The title compound was obtained by the condensation of ethylenediamine and (5
E,5
E,6
Z,6
Z)-6,6-[ethane-1,2-diylbis(azanylylidene)]bis{5-[2-(4-fluorophenyl)hydrazono)-3,3-dimethylcyclohexanone} in ethanol and crystallized as a 1:2.5 hydrate containing two different conformers stabilized by intramolecular N—H

N and linked by O—H

O (involving the water molecules) hydrogen bonds.
Supporting information
CCDC reference: 2153643
Key indicators
Structure: I
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.058
- wR factor = 0.193
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT041_ALERT_1_C Calc. and Reported SumFormula Strings Differ Please Check
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ Please Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including O1W 0.159 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including O2W 0.138 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including O3W 0.184 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including O4W 0.180 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including O5W 0.175 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including O6W 0.149 Check
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00493 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D H1WA ..H3WA . 2.13 Ang.
2-x,1-y,1-z = 5_766 Check
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -4.141 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.596 2 Report
Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 1 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 3 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 15 Report
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ... 0.500 Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 1 Report
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records 1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records 1 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records 1 Report
PLAT300_ALERT_4_G Atom Site Occupancy of O4W Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H4WA Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H4WB Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of O5W Constrained at 0.125 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H5WA Constrained at 0.125 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H5WB Constrained at 0.125 Check
PLAT300_ALERT_4_G Atom Site Occupancy of O6W Constrained at 0.125 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6WA Constrained at 0.125 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6WB Constrained at 0.125 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 6 ) 100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 7 ) 100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 8 ) 100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd 6 ) 1.50 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd 7 ) 0.38 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd 8 ) 0.38 Check
PLAT417_ALERT_2_G Short Inter D-H..H-D H3WA ..H4WB . 1.28 Ang.
x,y,z = 1_555 Check
PLAT417_ALERT_2_G Short Inter D-H..H-D H3WA ..H5WA . 1.63 Ang.
x,y,z = 1_555 Check
PLAT417_ALERT_2_G Short Inter D-H..H-D H3WA ..H5WB . 1.90 Ang.
x,y,z = 1_555 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact F3 ..F3 . 2.84 Ang.
3/2-x,1/2-y,1-z = 7_656 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H24A ..O3 . 2.65 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 12 Note
PLAT728_ALERT_1_G D-H..A Calc 117.00, Rep 118.10 Dev... 1.10 Degree
O5W -H5WB -O5W 1_555 1_555 2_755 # 22 Check
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters 1 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 25 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary . Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 3 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File 4 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ........... 4.5 Low
PLAT967_ALERT_5_G Note: Two-Theta Cutoff Value in Embedded .res .. 50.1 Degree
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
12 ALERT level C = Check. Ensure it is not caused by an omission or oversight
38 ALERT level G = General information/check it is not something unexpected
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
15 ALERT type 2 Indicator that the structure model may be wrong or deficient
6 ALERT type 3 Indicator that the structure quality may be low
22 ALERT type 4 Improvement, methodology, query or suggestion
2 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXT2013/1 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
(5
E,5'
E,6
Z,6'
Z)-6,6'-[Ethane-1,2-diylbis(azanylylidene)]bis{5-[2-(4-fluorophenyl)hydrazono]-3,3-dimethylcyclohexanone} 2.5-hydrate
top
Crystal data top
C30H34F2N6O2·2.5H2O | F(000) = 3780 |
Mr = 593.67 | Dx = 1.267 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 22.7715 (19) Å | Cell parameters from 2620 reflections |
b = 17.2794 (15) Å | θ = 2.5–18.8° |
c = 25.640 (3) Å | µ = 0.10 mm−1 |
β = 112.297 (1)° | T = 296 K |
V = 9334.2 (16) Å3 | Prism, colourless |
Z = 12 | 0.16 × 0.14 × 0.11 mm |
Data collection top
Bruker APEXII CCD diffractometer | Rint = 0.070 |
φ and ω scans | θmax = 25.1°, θmin = 1.9° |
37069 measured reflections | h = −27→27 |
8249 independent reflections | k = −20→20 |
4099 reflections with I > 2σ(I) | l = −30→30 |
Refinement top
Refinement on F2 | 25 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.193 | w = 1/[σ2(Fo2) + (0.0988P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
8249 reflections | Δρmax = 0.20 e Å−3 |
601 parameters | Δρmin = −0.29 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
F2 | 1.09554 (9) | 0.57702 (14) | 0.53005 (9) | 0.0952 (7) | |
O6 | 0.89907 (11) | 0.85004 (13) | 0.36530 (9) | 0.0707 (7) | |
N9 | 0.95271 (11) | 0.63828 (14) | 0.27726 (10) | 0.0497 (6) | |
H9 | 0.914706 | 0.638997 | 0.252226 | 0.060* | |
F3 | 0.76710 (10) | 0.32116 (12) | 0.48211 (10) | 0.1025 (8) | |
N10 | 0.86237 (11) | 0.75960 (14) | 0.27290 (10) | 0.0519 (6) | |
N2 | 0.75280 (11) | 0.67741 (14) | 0.31652 (10) | 0.0521 (6) | |
H2 | 0.791352 | 0.677251 | 0.340527 | 0.063* | |
N3 | 0.78027 (11) | 0.76386 (14) | 0.41673 (10) | 0.0530 (7) | |
H3 | 0.771048 | 0.715792 | 0.417904 | 0.064* | |
N1 | 0.84455 (11) | 0.71070 (15) | 0.23249 (10) | 0.0539 (7) | |
N7 | 0.83957 (12) | 0.55075 (15) | 0.32396 (11) | 0.0557 (7) | |
N6 | 0.85905 (12) | 0.60375 (15) | 0.36126 (11) | 0.0550 (7) | |
N4 | 0.82821 (12) | 0.67186 (16) | 0.51854 (11) | 0.0588 (7) | |
O7 | 0.79621 (12) | 0.44357 (15) | 0.24172 (11) | 0.0846 (8) | |
N5 | 0.79668 (12) | 0.63644 (15) | 0.47308 (11) | 0.0581 (7) | |
F4 | 0.60711 (11) | 0.74370 (16) | 0.06565 (10) | 0.1250 (9) | |
O3 | 0.89386 (14) | 0.75091 (17) | 0.61336 (10) | 0.0977 (9) | |
C12 | 0.96907 (13) | 0.69768 (16) | 0.31285 (11) | 0.0446 (7) | |
C7 | 0.92362 (13) | 0.75336 (17) | 0.31220 (12) | 0.0460 (7) | |
C8 | 0.93933 (15) | 0.80892 (17) | 0.35815 (12) | 0.0492 (7) | |
C20 | 0.73494 (14) | 0.61741 (17) | 0.28199 (12) | 0.0499 (8) | |
C10 | 1.05603 (13) | 0.78558 (17) | 0.37729 (12) | 0.0509 (8) | |
C13 | 0.99160 (14) | 0.57224 (16) | 0.27573 (12) | 0.0514 (8) | |
H13A | 0.968891 | 0.524959 | 0.276294 | 0.062* | |
H13B | 1.030349 | 0.572808 | 0.309210 | 0.062* | |
C11 | 1.03605 (13) | 0.70393 (17) | 0.35377 (12) | 0.0498 (7) | |
H11A | 1.063950 | 0.686857 | 0.335369 | 0.060* | |
H11B | 1.041915 | 0.669060 | 0.385002 | 0.060* | |
C40 | 0.92104 (14) | 0.59354 (18) | 0.40252 (13) | 0.0524 (8) | |
C21 | 0.77828 (15) | 0.55750 (17) | 0.28450 (13) | 0.0526 (8) | |
C31 | 0.83760 (14) | 0.75046 (19) | 0.51517 (12) | 0.0538 (8) | |
C26 | 0.81638 (13) | 0.79584 (17) | 0.46495 (13) | 0.0506 (8) | |
C4 | 0.78281 (14) | 0.72419 (19) | 0.19112 (12) | 0.0523 (8) | |
C34 | 0.79058 (14) | 0.55572 (19) | 0.47871 (14) | 0.0556 (8) | |
C39 | 0.76263 (15) | 0.5143 (2) | 0.42909 (14) | 0.0607 (9) | |
H39 | 0.749549 | 0.540146 | 0.394719 | 0.073* | |
C25 | 0.75416 (15) | 0.80125 (18) | 0.36141 (12) | 0.0580 (8) | |
H25A | 0.788441 | 0.819537 | 0.350919 | 0.070* | |
H25B | 0.728565 | 0.845438 | 0.362886 | 0.070* | |
C24 | 0.71388 (14) | 0.74392 (18) | 0.31816 (12) | 0.0559 (8) | |
H24A | 0.678742 | 0.726986 | 0.327934 | 0.067* | |
H24B | 0.696646 | 0.768255 | 0.281344 | 0.067* | |
C9 | 1.00665 (14) | 0.81378 (18) | 0.39906 (12) | 0.0544 (8) | |
H9A | 1.010664 | 0.783819 | 0.432237 | 0.065* | |
H9B | 1.015934 | 0.867263 | 0.410773 | 0.065* | |
C22 | 0.75933 (17) | 0.4957 (2) | 0.24298 (14) | 0.0634 (9) | |
C45 | 0.96325 (16) | 0.53591 (19) | 0.40083 (14) | 0.0595 (9) | |
H45 | 0.951641 | 0.500797 | 0.371137 | 0.071* | |
C41 | 0.93867 (14) | 0.64476 (19) | 0.44682 (14) | 0.0581 (8) | |
H41 | 0.910566 | 0.683324 | 0.447703 | 0.070* | |
C35 | 0.80994 (15) | 0.5166 (2) | 0.53017 (14) | 0.0626 (9) | |
H35 | 0.828554 | 0.543580 | 0.563835 | 0.075* | |
C36 | 0.80127 (16) | 0.4373 (2) | 0.53080 (17) | 0.0724 (10) | |
H36 | 0.813723 | 0.410494 | 0.564756 | 0.087* | |
C44 | 1.02267 (16) | 0.5316 (2) | 0.44389 (16) | 0.0675 (10) | |
H44 | 1.051675 | 0.494183 | 0.443113 | 0.081* | |
C19 | 0.66830 (15) | 0.61617 (18) | 0.23968 (13) | 0.0621 (9) | |
H19A | 0.665624 | 0.649403 | 0.208368 | 0.075* | |
H19B | 0.640637 | 0.637650 | 0.256904 | 0.075* | |
C43 | 1.03795 (16) | 0.5828 (2) | 0.48728 (16) | 0.0666 (10) | |
C30 | 0.87277 (17) | 0.7878 (2) | 0.56849 (15) | 0.0678 (9) | |
C28 | 0.89082 (16) | 0.90513 (19) | 0.51674 (14) | 0.0659 (9) | |
C27 | 0.83332 (15) | 0.87873 (17) | 0.46489 (13) | 0.0607 (9) | |
H27A | 0.796896 | 0.909788 | 0.462471 | 0.073* | |
H27B | 0.842091 | 0.888947 | 0.431352 | 0.073* | |
C18 | 0.64399 (16) | 0.5357 (2) | 0.21674 (14) | 0.0680 (10) | |
C38 | 0.75398 (16) | 0.4358 (2) | 0.42995 (16) | 0.0693 (10) | |
H38 | 0.734767 | 0.408362 | 0.396538 | 0.083* | |
C42 | 0.99769 (16) | 0.6397 (2) | 0.49014 (14) | 0.0666 (9) | |
H42 | 1.009572 | 0.674041 | 0.520310 | 0.080* | |
C3 | 0.74440 (16) | 0.7869 (2) | 0.19078 (14) | 0.0655 (9) | |
H3A | 0.758677 | 0.824248 | 0.218897 | 0.079* | |
C5 | 0.76179 (16) | 0.6708 (2) | 0.14840 (14) | 0.0672 (9) | |
H5 | 0.787844 | 0.629339 | 0.148330 | 0.081* | |
C15 | 1.06016 (17) | 0.83952 (19) | 0.33173 (14) | 0.0701 (10) | |
H15A | 1.088826 | 0.818125 | 0.316115 | 0.105* | |
H15B | 1.075407 | 0.889248 | 0.347916 | 0.105* | |
H15C | 1.018841 | 0.845162 | 0.302490 | 0.105* | |
C29 | 0.88290 (17) | 0.8731 (2) | 0.56898 (14) | 0.0710 (10) | |
H29A | 0.920447 | 0.886039 | 0.601720 | 0.085* | |
H29B | 0.847052 | 0.898716 | 0.573198 | 0.085* | |
C37 | 0.77395 (16) | 0.3988 (2) | 0.48037 (19) | 0.0713 (10) | |
C23 | 0.69345 (16) | 0.4967 (2) | 0.19936 (14) | 0.0726 (10) | |
H23A | 0.680241 | 0.443726 | 0.188760 | 0.087* | |
H23B | 0.694256 | 0.522801 | 0.166131 | 0.087* | |
C14 | 1.12089 (15) | 0.7801 (2) | 0.42564 (14) | 0.0742 (10) | |
H14A | 1.118189 | 0.745758 | 0.454065 | 0.111* | |
H14B | 1.133661 | 0.830553 | 0.441640 | 0.111* | |
H14C | 1.151542 | 0.760639 | 0.411575 | 0.111* | |
C46 | 0.66604 (18) | 0.7378 (3) | 0.10724 (16) | 0.0812 (11) | |
C6 | 0.70266 (19) | 0.6772 (3) | 0.10544 (15) | 0.0791 (11) | |
H6 | 0.688639 | 0.641151 | 0.076380 | 0.095* | |
C33 | 0.95173 (17) | 0.8743 (2) | 0.51310 (16) | 0.0831 (11) | |
H33A | 0.949259 | 0.818939 | 0.509510 | 0.125* | |
H33B | 0.987162 | 0.888138 | 0.546644 | 0.125* | |
H33C | 0.957199 | 0.896237 | 0.480848 | 0.125* | |
C17 | 0.63175 (18) | 0.4872 (2) | 0.26157 (17) | 0.0875 (12) | |
H17A | 0.670640 | 0.481196 | 0.293764 | 0.131* | |
H17B | 0.616002 | 0.437181 | 0.246323 | 0.131* | |
H17C | 0.600946 | 0.512764 | 0.272725 | 0.131* | |
C2 | 0.68508 (18) | 0.7934 (2) | 0.14860 (16) | 0.0795 (11) | |
H2A | 0.658518 | 0.834447 | 0.148160 | 0.095* | |
C16 | 0.58150 (18) | 0.5454 (2) | 0.16554 (17) | 0.0996 (14) | |
H16A | 0.550401 | 0.569113 | 0.177259 | 0.149* | |
H16B | 0.566489 | 0.495546 | 0.149430 | 0.149* | |
H16C | 0.588558 | 0.577506 | 0.137932 | 0.149* | |
C32 | 0.8926 (2) | 0.9931 (2) | 0.51835 (18) | 0.0964 (13) | |
H32A | 0.896750 | 1.012411 | 0.484791 | 0.145* | |
H32B | 0.928180 | 1.010059 | 0.550779 | 0.145* | |
H32C | 0.854080 | 1.012447 | 0.520502 | 0.145* | |
O2W | 0.85971 (16) | 0.5119 (2) | 0.17268 (14) | 0.1381 (12) | |
H2WA | 0.840883 | 0.493144 | 0.192778 | 0.207* | |
H2WB | 0.879123 | 0.473704 | 0.165798 | 0.207* | |
O1W | 0.93443 (17) | 0.6011 (2) | 0.65403 (17) | 0.1587 (15) | |
H1WA | 0.970580 | 0.620651 | 0.672785 | 0.238* | |
H1WB | 0.910130 | 0.639951 | 0.641847 | 0.238* | |
O3W | 0.92308 (17) | 0.3840 (2) | 0.2815 (2) | 0.1847 (19) | |
H3WA | 0.935932 | 0.338346 | 0.279348 | 0.277* | |
H3WB | 0.882892 | 0.380027 | 0.269188 | 0.277* | |
O4W | 0.9769 (4) | 0.2282 (5) | 0.2984 (4) | 0.180 (3) | 0.5 |
H4WA | 0.985140 | 0.227073 | 0.268724 | 0.270* | 0.5 |
H4WB | 0.962601 | 0.273503 | 0.298895 | 0.270* | 0.5 |
O5W | 0.9411 (16) | 0.241 (2) | 0.2313 (14) | 0.175 (4) | 0.125 |
H5WA | 0.911013 | 0.265707 | 0.236069 | 0.263* | 0.125 |
H5WB | 0.969813 | 0.275397 | 0.236599 | 0.263* | 0.125 |
O6W | 0.9656 (16) | 0.1682 (18) | 0.2174 (11) | 0.152 (11) | 0.125 |
H6WA | 0.942959 | 0.192682 | 0.187885 | 0.229* | 0.125 |
H6WB | 0.949669 | 0.123032 | 0.212835 | 0.229* | 0.125 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F2 | 0.0492 (12) | 0.1286 (19) | 0.0893 (15) | 0.0052 (12) | 0.0055 (12) | 0.0275 (14) |
O6 | 0.0634 (15) | 0.0765 (16) | 0.0659 (15) | 0.0190 (13) | 0.0174 (12) | −0.0113 (12) |
N9 | 0.0451 (14) | 0.0494 (15) | 0.0520 (15) | −0.0007 (12) | 0.0157 (12) | −0.0013 (13) |
F3 | 0.0878 (16) | 0.0592 (13) | 0.133 (2) | −0.0079 (11) | 0.0110 (14) | 0.0246 (13) |
N10 | 0.0481 (16) | 0.0540 (16) | 0.0504 (16) | 0.0013 (13) | 0.0153 (14) | 0.0014 (13) |
N2 | 0.0465 (15) | 0.0554 (16) | 0.0465 (15) | −0.0008 (13) | 0.0088 (12) | −0.0035 (13) |
N3 | 0.0575 (16) | 0.0460 (15) | 0.0480 (15) | −0.0019 (12) | 0.0114 (13) | 0.0015 (12) |
N1 | 0.0471 (16) | 0.0600 (17) | 0.0506 (16) | −0.0003 (13) | 0.0141 (14) | 0.0011 (14) |
N7 | 0.0548 (17) | 0.0560 (17) | 0.0556 (16) | −0.0069 (13) | 0.0200 (15) | −0.0017 (14) |
N6 | 0.0489 (16) | 0.0614 (17) | 0.0512 (16) | −0.0062 (13) | 0.0150 (14) | −0.0006 (14) |
N4 | 0.0586 (17) | 0.0617 (19) | 0.0545 (17) | 0.0017 (14) | 0.0194 (14) | 0.0029 (14) |
O7 | 0.0789 (18) | 0.0724 (17) | 0.100 (2) | −0.0005 (14) | 0.0314 (16) | −0.0241 (15) |
N5 | 0.0596 (17) | 0.0575 (18) | 0.0527 (17) | −0.0005 (14) | 0.0162 (14) | −0.0002 (14) |
F4 | 0.0794 (16) | 0.154 (2) | 0.0920 (17) | 0.0178 (15) | −0.0236 (14) | 0.0128 (16) |
O3 | 0.123 (2) | 0.098 (2) | 0.0496 (15) | −0.0072 (17) | 0.0072 (16) | 0.0027 (15) |
C12 | 0.0480 (18) | 0.0432 (18) | 0.0428 (17) | −0.0026 (14) | 0.0174 (15) | 0.0015 (14) |
C7 | 0.0442 (18) | 0.0466 (17) | 0.0447 (17) | 0.0040 (14) | 0.0141 (15) | 0.0048 (14) |
C8 | 0.0532 (19) | 0.0493 (18) | 0.0453 (18) | 0.0078 (16) | 0.0189 (16) | 0.0036 (15) |
C20 | 0.0531 (19) | 0.0517 (19) | 0.0415 (17) | −0.0090 (16) | 0.0143 (15) | 0.0034 (15) |
C10 | 0.0459 (18) | 0.0524 (19) | 0.0500 (18) | −0.0059 (15) | 0.0134 (15) | −0.0055 (15) |
C13 | 0.0559 (19) | 0.0392 (16) | 0.0572 (19) | −0.0019 (15) | 0.0193 (16) | 0.0004 (14) |
C11 | 0.0439 (18) | 0.0504 (18) | 0.0518 (18) | 0.0026 (15) | 0.0146 (15) | 0.0012 (15) |
C40 | 0.0451 (19) | 0.056 (2) | 0.056 (2) | −0.0016 (16) | 0.0188 (17) | 0.0053 (16) |
C21 | 0.0502 (19) | 0.0482 (19) | 0.056 (2) | −0.0041 (16) | 0.0163 (17) | −0.0007 (16) |
C31 | 0.0536 (19) | 0.060 (2) | 0.0438 (18) | 0.0015 (16) | 0.0141 (16) | −0.0051 (16) |
C26 | 0.0447 (18) | 0.0520 (19) | 0.055 (2) | 0.0034 (15) | 0.0194 (16) | −0.0079 (16) |
C4 | 0.0476 (19) | 0.065 (2) | 0.0389 (17) | 0.0007 (17) | 0.0104 (15) | 0.0049 (16) |
C34 | 0.0494 (19) | 0.057 (2) | 0.061 (2) | 0.0031 (16) | 0.0225 (17) | 0.0116 (17) |
C39 | 0.058 (2) | 0.062 (2) | 0.056 (2) | 0.0010 (17) | 0.0154 (17) | 0.0074 (18) |
C25 | 0.062 (2) | 0.0522 (19) | 0.0497 (19) | 0.0048 (16) | 0.0101 (17) | 0.0060 (16) |
C24 | 0.0528 (19) | 0.057 (2) | 0.0486 (18) | 0.0060 (16) | 0.0086 (16) | 0.0040 (16) |
C9 | 0.057 (2) | 0.0558 (19) | 0.0472 (18) | −0.0013 (16) | 0.0162 (16) | −0.0041 (15) |
C22 | 0.067 (2) | 0.056 (2) | 0.065 (2) | −0.0082 (19) | 0.023 (2) | −0.0040 (18) |
C45 | 0.061 (2) | 0.061 (2) | 0.061 (2) | 0.0007 (18) | 0.0274 (19) | 0.0072 (17) |
C41 | 0.0442 (19) | 0.060 (2) | 0.065 (2) | 0.0024 (16) | 0.0155 (18) | 0.0031 (18) |
C35 | 0.057 (2) | 0.074 (2) | 0.056 (2) | 0.0042 (18) | 0.0200 (17) | 0.0082 (18) |
C36 | 0.062 (2) | 0.072 (3) | 0.079 (3) | 0.003 (2) | 0.022 (2) | 0.030 (2) |
C44 | 0.051 (2) | 0.071 (2) | 0.084 (3) | 0.0148 (18) | 0.028 (2) | 0.024 (2) |
C19 | 0.054 (2) | 0.062 (2) | 0.056 (2) | −0.0027 (16) | 0.0051 (17) | −0.0009 (17) |
C43 | 0.044 (2) | 0.082 (3) | 0.066 (2) | −0.002 (2) | 0.0114 (19) | 0.021 (2) |
C30 | 0.067 (2) | 0.077 (3) | 0.055 (2) | 0.006 (2) | 0.0184 (19) | −0.005 (2) |
C28 | 0.065 (2) | 0.061 (2) | 0.066 (2) | −0.0066 (18) | 0.0187 (19) | −0.0158 (18) |
C27 | 0.064 (2) | 0.053 (2) | 0.061 (2) | 0.0050 (16) | 0.0187 (18) | −0.0070 (16) |
C18 | 0.057 (2) | 0.067 (2) | 0.063 (2) | −0.0098 (18) | 0.0033 (18) | −0.0026 (18) |
C38 | 0.062 (2) | 0.062 (2) | 0.072 (2) | −0.0038 (18) | 0.013 (2) | 0.004 (2) |
C42 | 0.052 (2) | 0.075 (2) | 0.065 (2) | −0.0087 (19) | 0.0135 (19) | −0.0012 (19) |
C3 | 0.067 (2) | 0.068 (2) | 0.055 (2) | 0.0049 (19) | 0.0147 (19) | 0.0068 (17) |
C5 | 0.060 (2) | 0.081 (2) | 0.054 (2) | 0.0016 (19) | 0.0142 (19) | −0.0019 (19) |
C15 | 0.079 (2) | 0.058 (2) | 0.081 (2) | −0.0153 (18) | 0.039 (2) | 0.0003 (19) |
C29 | 0.073 (2) | 0.076 (3) | 0.057 (2) | 0.006 (2) | 0.0171 (19) | −0.0179 (19) |
C37 | 0.054 (2) | 0.055 (2) | 0.095 (3) | −0.0012 (18) | 0.017 (2) | 0.009 (2) |
C23 | 0.075 (3) | 0.065 (2) | 0.067 (2) | −0.009 (2) | 0.014 (2) | −0.0092 (18) |
C14 | 0.057 (2) | 0.077 (3) | 0.077 (2) | −0.0035 (19) | 0.0117 (19) | −0.016 (2) |
C46 | 0.061 (2) | 0.102 (3) | 0.058 (2) | 0.002 (2) | −0.004 (2) | 0.012 (2) |
C6 | 0.072 (3) | 0.095 (3) | 0.052 (2) | −0.005 (2) | 0.004 (2) | −0.005 (2) |
C33 | 0.063 (2) | 0.104 (3) | 0.077 (3) | −0.010 (2) | 0.021 (2) | −0.019 (2) |
C17 | 0.077 (3) | 0.082 (3) | 0.098 (3) | −0.018 (2) | 0.027 (2) | 0.005 (2) |
C2 | 0.070 (3) | 0.085 (3) | 0.076 (3) | 0.024 (2) | 0.018 (2) | 0.020 (2) |
C16 | 0.075 (3) | 0.091 (3) | 0.091 (3) | −0.010 (2) | −0.016 (2) | −0.018 (2) |
C32 | 0.118 (4) | 0.063 (3) | 0.099 (3) | −0.015 (2) | 0.031 (3) | −0.025 (2) |
O2W | 0.137 (3) | 0.153 (3) | 0.134 (3) | 0.008 (2) | 0.062 (2) | 0.002 (2) |
O1W | 0.130 (3) | 0.116 (3) | 0.188 (4) | −0.014 (2) | 0.013 (3) | 0.049 (2) |
O3W | 0.111 (3) | 0.134 (3) | 0.298 (6) | −0.003 (2) | 0.066 (3) | 0.025 (3) |
O4W | 0.160 (6) | 0.137 (6) | 0.170 (6) | −0.040 (5) | −0.019 (5) | 0.015 (5) |
O5W | 0.157 (7) | 0.138 (7) | 0.166 (7) | −0.038 (6) | −0.011 (6) | 0.015 (6) |
O6W | 0.19 (3) | 0.13 (2) | 0.12 (2) | 0.05 (2) | 0.05 (2) | 0.050 (18) |
Geometric parameters (Å, º) top
F2—C43 | 1.357 (4) | C36—C37 | 1.375 (5) |
O6—C8 | 1.227 (3) | C36—H36 | 0.9300 |
N9—C12 | 1.329 (3) | C44—C43 | 1.360 (5) |
N9—C13 | 1.454 (4) | C44—H44 | 0.9300 |
N9—H9 | 0.8600 | C19—C18 | 1.529 (4) |
F3—C37 | 1.353 (4) | C19—H19A | 0.9700 |
N10—N1 | 1.278 (3) | C19—H19B | 0.9700 |
N10—C7 | 1.380 (3) | C43—C42 | 1.365 (5) |
N2—C20 | 1.323 (3) | C30—C29 | 1.491 (5) |
N2—C24 | 1.461 (4) | C28—C32 | 1.521 (5) |
N2—H2 | 0.8600 | C28—C33 | 1.522 (5) |
N3—C26 | 1.319 (3) | C28—C29 | 1.522 (5) |
N3—C25 | 1.464 (3) | C28—C27 | 1.539 (4) |
N3—H3 | 0.8600 | C27—H27A | 0.9700 |
N1—C4 | 1.423 (4) | C27—H27B | 0.9700 |
N7—N6 | 1.276 (3) | C18—C23 | 1.517 (5) |
N7—C21 | 1.383 (4) | C18—C17 | 1.531 (5) |
N6—C40 | 1.418 (4) | C18—C16 | 1.536 (4) |
N4—N5 | 1.270 (3) | C38—C37 | 1.357 (5) |
N4—C31 | 1.383 (4) | C38—H38 | 0.9300 |
O7—C22 | 1.240 (4) | C42—H42 | 0.9300 |
N5—C34 | 1.414 (4) | C3—C2 | 1.378 (5) |
F4—C46 | 1.365 (4) | C3—H3A | 0.9300 |
O3—C30 | 1.242 (4) | C5—C6 | 1.383 (5) |
C12—C7 | 1.409 (4) | C5—H5 | 0.9300 |
C12—C11 | 1.491 (4) | C15—H15A | 0.9600 |
C7—C8 | 1.455 (4) | C15—H15B | 0.9600 |
C8—C9 | 1.496 (4) | C15—H15C | 0.9600 |
C20—C21 | 1.415 (4) | C29—H29A | 0.9700 |
C20—C19 | 1.494 (4) | C29—H29B | 0.9700 |
C10—C9 | 1.513 (4) | C23—H23A | 0.9700 |
C10—C15 | 1.525 (4) | C23—H23B | 0.9700 |
C10—C14 | 1.529 (4) | C14—H14A | 0.9600 |
C10—C11 | 1.534 (4) | C14—H14B | 0.9600 |
C13—C13i | 1.507 (6) | C14—H14C | 0.9600 |
C13—H13A | 0.9700 | C46—C6 | 1.350 (5) |
C13—H13B | 0.9700 | C46—C2 | 1.373 (5) |
C11—H11A | 0.9700 | C6—H6 | 0.9300 |
C11—H11B | 0.9700 | C33—H33A | 0.9600 |
C40—C41 | 1.374 (4) | C33—H33B | 0.9600 |
C40—C45 | 1.396 (4) | C33—H33C | 0.9600 |
C21—C22 | 1.453 (4) | C17—H17A | 0.9600 |
C31—C26 | 1.426 (4) | C17—H17B | 0.9600 |
C31—C30 | 1.448 (4) | C17—H17C | 0.9600 |
C26—C27 | 1.483 (4) | C2—H2A | 0.9300 |
C4—C5 | 1.372 (4) | C16—H16A | 0.9600 |
C4—C3 | 1.390 (4) | C16—H16B | 0.9600 |
C34—C39 | 1.386 (4) | C16—H16C | 0.9600 |
C34—C35 | 1.397 (4) | C32—H32A | 0.9600 |
C39—C38 | 1.374 (4) | C32—H32B | 0.9600 |
C39—H39 | 0.9300 | C32—H32C | 0.9600 |
C25—C24 | 1.510 (4) | O2W—H2WA | 0.8500 |
C25—H25A | 0.9700 | O2W—H2WB | 0.8497 |
C25—H25B | 0.9700 | O1W—H1WA | 0.8499 |
C24—H24A | 0.9700 | O1W—H1WB | 0.8500 |
C24—H24B | 0.9700 | O3W—H3WA | 0.8500 |
C9—H9A | 0.9700 | O3W—H3WB | 0.8500 |
C9—H9B | 0.9700 | O4W—H4WA | 0.8503 |
C22—C23 | 1.493 (4) | O4W—H4WB | 0.8499 |
C45—C44 | 1.386 (4) | O5W—H5WA | 0.8501 |
C45—H45 | 0.9300 | O5W—H5WB | 0.8501 |
C41—C42 | 1.384 (4) | O6W—O6Wi | 1.80 (6) |
C41—H41 | 0.9300 | O6W—H6WA | 0.8499 |
C35—C36 | 1.385 (5) | O6W—H6WB | 0.8500 |
C35—H35 | 0.9300 | | |
| | | |
C12—N9—C13 | 127.6 (3) | C18—C19—H19B | 108.7 |
C12—N9—H9 | 116.2 | H19A—C19—H19B | 107.6 |
C13—N9—H9 | 116.2 | F2—C43—C44 | 118.8 (3) |
N1—N10—C7 | 117.5 (2) | F2—C43—C42 | 118.2 (4) |
C20—N2—C24 | 126.8 (3) | C44—C43—C42 | 123.0 (3) |
C20—N2—H2 | 116.6 | O3—C30—C31 | 121.8 (3) |
C24—N2—H2 | 116.6 | O3—C30—C29 | 119.7 (3) |
C26—N3—C25 | 127.1 (3) | C31—C30—C29 | 118.5 (3) |
C26—N3—H3 | 116.5 | C32—C28—C33 | 109.7 (3) |
C25—N3—H3 | 116.5 | C32—C28—C29 | 110.5 (3) |
N10—N1—C4 | 114.6 (3) | C33—C28—C29 | 110.0 (3) |
N6—N7—C21 | 117.1 (3) | C32—C28—C27 | 109.0 (3) |
N7—N6—C40 | 115.8 (3) | C33—C28—C27 | 109.9 (3) |
N5—N4—C31 | 117.6 (3) | C29—C28—C27 | 107.8 (3) |
N4—N5—C34 | 115.1 (3) | C26—C27—C28 | 114.9 (3) |
N9—C12—C7 | 120.4 (3) | C26—C27—H27A | 108.5 |
N9—C12—C11 | 119.0 (3) | C28—C27—H27A | 108.5 |
C7—C12—C11 | 120.6 (3) | C26—C27—H27B | 108.5 |
N10—C7—C12 | 126.6 (3) | C28—C27—H27B | 108.5 |
N10—C7—C8 | 114.2 (3) | H27A—C27—H27B | 107.5 |
C12—C7—C8 | 119.2 (3) | C23—C18—C19 | 108.4 (3) |
O6—C8—C7 | 122.3 (3) | C23—C18—C17 | 110.1 (3) |
O6—C8—C9 | 119.2 (3) | C19—C18—C17 | 110.6 (3) |
C7—C8—C9 | 118.5 (3) | C23—C18—C16 | 110.3 (3) |
N2—C20—C21 | 120.7 (3) | C19—C18—C16 | 108.2 (3) |
N2—C20—C19 | 117.8 (3) | C17—C18—C16 | 109.1 (3) |
C21—C20—C19 | 121.4 (3) | C37—C38—C39 | 118.9 (3) |
C9—C10—C15 | 110.9 (3) | C37—C38—H38 | 120.6 |
C9—C10—C14 | 110.2 (2) | C39—C38—H38 | 120.6 |
C15—C10—C14 | 109.7 (3) | C43—C42—C41 | 118.0 (3) |
C9—C10—C11 | 106.8 (2) | C43—C42—H42 | 121.0 |
C15—C10—C11 | 110.9 (2) | C41—C42—H42 | 121.0 |
C14—C10—C11 | 108.3 (2) | C2—C3—C4 | 119.7 (3) |
N9—C13—C13i | 112.5 (2) | C2—C3—H3A | 120.1 |
N9—C13—H13A | 109.1 | C4—C3—H3A | 120.1 |
C13i—C13—H13A | 109.1 | C4—C5—C6 | 121.4 (3) |
N9—C13—H13B | 109.1 | C4—C5—H5 | 119.3 |
C13i—C13—H13B | 109.1 | C6—C5—H5 | 119.3 |
H13A—C13—H13B | 107.8 | C10—C15—H15A | 109.5 |
C12—C11—C10 | 114.5 (2) | C10—C15—H15B | 109.5 |
C12—C11—H11A | 108.6 | H15A—C15—H15B | 109.5 |
C10—C11—H11A | 108.6 | C10—C15—H15C | 109.5 |
C12—C11—H11B | 108.6 | H15A—C15—H15C | 109.5 |
C10—C11—H11B | 108.6 | H15B—C15—H15C | 109.5 |
H11A—C11—H11B | 107.6 | C30—C29—C28 | 114.9 (3) |
C41—C40—C45 | 119.8 (3) | C30—C29—H29A | 108.5 |
C41—C40—N6 | 115.6 (3) | C28—C29—H29A | 108.5 |
C45—C40—N6 | 124.6 (3) | C30—C29—H29B | 108.5 |
N7—C21—C20 | 126.0 (3) | C28—C29—H29B | 108.5 |
N7—C21—C22 | 114.2 (3) | H29A—C29—H29B | 107.5 |
C20—C21—C22 | 119.8 (3) | F3—C37—C38 | 119.8 (4) |
N4—C31—C26 | 126.1 (3) | F3—C37—C36 | 117.7 (4) |
N4—C31—C30 | 115.0 (3) | C38—C37—C36 | 122.5 (3) |
C26—C31—C30 | 118.9 (3) | C22—C23—C18 | 115.6 (3) |
N3—C26—C31 | 119.6 (3) | C22—C23—H23A | 108.4 |
N3—C26—C27 | 118.3 (3) | C18—C23—H23A | 108.4 |
C31—C26—C27 | 122.2 (3) | C22—C23—H23B | 108.4 |
C5—C4—C3 | 119.4 (3) | C18—C23—H23B | 108.4 |
C5—C4—N1 | 115.6 (3) | H23A—C23—H23B | 107.4 |
C3—C4—N1 | 125.0 (3) | C10—C14—H14A | 109.5 |
C39—C34—C35 | 119.2 (3) | C10—C14—H14B | 109.5 |
C39—C34—N5 | 116.3 (3) | H14A—C14—H14B | 109.5 |
C35—C34—N5 | 124.5 (3) | C10—C14—H14C | 109.5 |
C38—C39—C34 | 120.9 (3) | H14A—C14—H14C | 109.5 |
C38—C39—H39 | 119.5 | H14B—C14—H14C | 109.5 |
C34—C39—H39 | 119.5 | C6—C46—F4 | 117.9 (4) |
N3—C25—C24 | 109.4 (2) | C6—C46—C2 | 123.4 (3) |
N3—C25—H25A | 109.8 | F4—C46—C2 | 118.7 (4) |
C24—C25—H25A | 109.8 | C46—C6—C5 | 117.6 (4) |
N3—C25—H25B | 109.8 | C46—C6—H6 | 121.2 |
C24—C25—H25B | 109.8 | C5—C6—H6 | 121.2 |
H25A—C25—H25B | 108.2 | C28—C33—H33A | 109.5 |
N2—C24—C25 | 109.3 (2) | C28—C33—H33B | 109.5 |
N2—C24—H24A | 109.8 | H33A—C33—H33B | 109.5 |
C25—C24—H24A | 109.8 | C28—C33—H33C | 109.5 |
N2—C24—H24B | 109.8 | H33A—C33—H33C | 109.5 |
C25—C24—H24B | 109.8 | H33B—C33—H33C | 109.5 |
H24A—C24—H24B | 108.3 | C18—C17—H17A | 109.5 |
C8—C9—C10 | 115.5 (2) | C18—C17—H17B | 109.5 |
C8—C9—H9A | 108.4 | H17A—C17—H17B | 109.5 |
C10—C9—H9A | 108.4 | C18—C17—H17C | 109.5 |
C8—C9—H9B | 108.4 | H17A—C17—H17C | 109.5 |
C10—C9—H9B | 108.4 | H17B—C17—H17C | 109.5 |
H9A—C9—H9B | 107.5 | C46—C2—C3 | 118.5 (4) |
O7—C22—C21 | 122.5 (3) | C46—C2—H2A | 120.7 |
O7—C22—C23 | 119.2 (3) | C3—C2—H2A | 120.7 |
C21—C22—C23 | 118.3 (3) | C18—C16—H16A | 109.5 |
C44—C45—C40 | 119.3 (3) | C18—C16—H16B | 109.5 |
C44—C45—H45 | 120.4 | H16A—C16—H16B | 109.5 |
C40—C45—H45 | 120.4 | C18—C16—H16C | 109.5 |
C40—C41—C42 | 120.9 (3) | H16A—C16—H16C | 109.5 |
C40—C41—H41 | 119.6 | H16B—C16—H16C | 109.5 |
C42—C41—H41 | 119.6 | C28—C32—H32A | 109.5 |
C36—C35—C34 | 119.7 (3) | C28—C32—H32B | 109.5 |
C36—C35—H35 | 120.2 | H32A—C32—H32B | 109.5 |
C34—C35—H35 | 120.2 | C28—C32—H32C | 109.5 |
C37—C36—C35 | 118.9 (3) | H32A—C32—H32C | 109.5 |
C37—C36—H36 | 120.6 | H32B—C32—H32C | 109.5 |
C35—C36—H36 | 120.6 | H2WA—O2W—H2WB | 104.5 |
C43—C44—C45 | 119.1 (3) | H1WA—O1W—H1WB | 104.5 |
C43—C44—H44 | 120.5 | H3WA—O3W—H3WB | 104.5 |
C45—C44—H44 | 120.5 | H4WA—O4W—H4WB | 104.5 |
C20—C19—C18 | 114.3 (3) | H5WA—O5W—H5WB | 104.5 |
C20—C19—H19A | 108.7 | O6Wi—O6W—H6WA | 147.7 |
C18—C19—H19A | 108.7 | O6Wi—O6W—H6WB | 107.6 |
C20—C19—H19B | 108.7 | H6WA—O6W—H6WB | 104.5 |
| | | |
C7—N10—N1—C4 | −175.2 (2) | N7—C21—C22—C23 | 178.6 (3) |
C21—N7—N6—C40 | 177.4 (2) | C20—C21—C22—C23 | −1.3 (4) |
C31—N4—N5—C34 | 177.7 (3) | C41—C40—C45—C44 | −0.4 (4) |
C13—N9—C12—C7 | −173.7 (2) | N6—C40—C45—C44 | −179.7 (3) |
C13—N9—C12—C11 | 5.7 (4) | C45—C40—C41—C42 | −0.5 (5) |
N1—N10—C7—C12 | −0.6 (4) | N6—C40—C41—C42 | 178.9 (3) |
N1—N10—C7—C8 | −177.4 (2) | C39—C34—C35—C36 | 0.4 (5) |
N9—C12—C7—N10 | −8.4 (4) | N5—C34—C35—C36 | 179.5 (3) |
C11—C12—C7—N10 | 172.2 (3) | C34—C35—C36—C37 | 0.4 (5) |
N9—C12—C7—C8 | 168.2 (2) | C40—C45—C44—C43 | 1.2 (5) |
C11—C12—C7—C8 | −11.2 (4) | N2—C20—C19—C18 | −158.9 (3) |
N10—C7—C8—O6 | 9.6 (4) | C21—C20—C19—C18 | 22.5 (4) |
C12—C7—C8—O6 | −167.4 (3) | C45—C44—C43—F2 | 178.3 (3) |
N10—C7—C8—C9 | −172.5 (2) | C45—C44—C43—C42 | −1.1 (5) |
C12—C7—C8—C9 | 10.4 (4) | N4—C31—C30—O3 | 1.6 (5) |
C24—N2—C20—C21 | 178.8 (3) | C26—C31—C30—O3 | −178.1 (3) |
C24—N2—C20—C19 | 0.2 (4) | N4—C31—C30—C29 | −177.7 (3) |
C12—N9—C13—C13i | −111.6 (3) | C26—C31—C30—C29 | 2.7 (5) |
N9—C12—C11—C10 | 159.0 (3) | N3—C26—C27—C28 | −161.6 (3) |
C7—C12—C11—C10 | −21.6 (4) | C31—C26—C27—C28 | 18.7 (4) |
C9—C10—C11—C12 | 51.5 (3) | C32—C28—C27—C26 | −166.1 (3) |
C15—C10—C11—C12 | −69.4 (3) | C33—C28—C27—C26 | 73.8 (4) |
C14—C10—C11—C12 | 170.2 (3) | C29—C28—C27—C26 | −46.1 (4) |
N7—N6—C40—C41 | −171.5 (3) | C20—C19—C18—C23 | −48.5 (4) |
N7—N6—C40—C45 | 7.8 (4) | C20—C19—C18—C17 | 72.4 (4) |
N6—N7—C21—C20 | −0.6 (4) | C20—C19—C18—C16 | −168.1 (3) |
N6—N7—C21—C22 | 179.5 (3) | C34—C39—C38—C37 | −0.7 (5) |
N2—C20—C21—N7 | 5.5 (5) | F2—C43—C42—C41 | −179.1 (3) |
C19—C20—C21—N7 | −175.9 (3) | C44—C43—C42—C41 | 0.3 (5) |
N2—C20—C21—C22 | −174.6 (3) | C40—C41—C42—C43 | 0.5 (5) |
C19—C20—C21—C22 | 4.0 (4) | C5—C4—C3—C2 | 1.9 (5) |
N5—N4—C31—C26 | −1.5 (5) | N1—C4—C3—C2 | −179.4 (3) |
N5—N4—C31—C30 | 178.8 (3) | C3—C4—C5—C6 | −1.1 (5) |
C25—N3—C26—C31 | 179.9 (3) | N1—C4—C5—C6 | −179.9 (3) |
C25—N3—C26—C27 | 0.1 (4) | O3—C30—C29—C28 | 146.9 (3) |
N4—C31—C26—N3 | 5.5 (5) | C31—C30—C29—C28 | −33.8 (4) |
C30—C31—C26—N3 | −174.9 (3) | C32—C28—C29—C30 | 173.0 (3) |
N4—C31—C26—C27 | −174.8 (3) | C33—C28—C29—C30 | −65.8 (4) |
C30—C31—C26—C27 | 4.8 (4) | C27—C28—C29—C30 | 54.0 (4) |
N10—N1—C4—C5 | −177.7 (3) | C39—C38—C37—F3 | −178.6 (3) |
N10—N1—C4—C3 | 3.6 (4) | C39—C38—C37—C36 | 1.5 (5) |
N4—N5—C34—C39 | −173.0 (3) | C35—C36—C37—F3 | 178.8 (3) |
N4—N5—C34—C35 | 7.8 (4) | C35—C36—C37—C38 | −1.3 (5) |
C35—C34—C39—C38 | −0.2 (5) | O7—C22—C23—C18 | 153.5 (3) |
N5—C34—C39—C38 | −179.4 (3) | C21—C22—C23—C18 | −28.2 (5) |
C26—N3—C25—C24 | −178.3 (3) | C19—C18—C23—C22 | 51.9 (4) |
C20—N2—C24—C25 | −176.4 (3) | C17—C18—C23—C22 | −69.2 (4) |
N3—C25—C24—N2 | −59.1 (3) | C16—C18—C23—C22 | 170.2 (3) |
O6—C8—C9—C10 | −158.5 (3) | F4—C46—C6—C5 | −178.7 (3) |
C7—C8—C9—C10 | 23.6 (4) | C2—C46—C6—C5 | 1.3 (6) |
C15—C10—C9—C8 | 68.3 (3) | C4—C5—C6—C46 | −0.5 (5) |
C14—C10—C9—C8 | −170.0 (3) | C6—C46—C2—C3 | −0.5 (6) |
C11—C10—C9—C8 | −52.6 (3) | F4—C46—C2—C3 | 179.5 (3) |
N7—C21—C22—O7 | −3.2 (5) | C4—C3—C2—C46 | −1.2 (5) |
C20—C21—C22—O7 | 176.8 (3) | | |
Symmetry code: (i) −x+2, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N9—H9···N1 | 0.86 | 1.93 | 2.609 (3) | 135 |
N2—H2···N6 | 0.86 | 1.91 | 2.585 (3) | 134 |
N3—H3···N5 | 0.86 | 1.90 | 2.582 (3) | 136 |
C13—H13B···O2Wi | 0.97 | 2.59 | 3.302 (4) | 130 |
C25—H25A···O6 | 0.97 | 2.46 | 3.370 (4) | 156 |
C24—H24A···O3ii | 0.97 | 2.65 | 3.518 (4) | 149 |
C24—H24A···O5Wiii | 0.97 | 2.58 | 3.27 (4) | 128 |
C27—H27B···O6 | 0.97 | 2.58 | 3.451 (4) | 149 |
C42—H42···F4iv | 0.93 | 2.52 | 3.218 (4) | 132 |
C5—H5···O2W | 0.93 | 2.53 | 3.441 (5) | 166 |
C23—H23A···O6v | 0.97 | 2.43 | 3.311 (4) | 151 |
O2W—H2WA···O7 | 0.85 | 2.08 | 2.926 (4) | 178 |
O2W—H2WB···O1Wvi | 0.85 | 1.91 | 2.749 (5) | 171 |
O1W—H1WA···O3Wvii | 0.85 | 2.26 | 3.042 (5) | 154 |
O1W—H1WB···O3 | 0.85 | 2.03 | 2.812 (4) | 152 |
O3W—H3WA···O4W | 0.85 | 2.09 | 2.921 (10) | 164 |
O3W—H3WA···O5W | 0.85 | 2.11 | 2.88 (4) | 151 |
O3W—H3WB···O7 | 0.85 | 2.13 | 2.866 (4) | 144 |
O4W—H4WA···O4Wi | 0.85 | 2.20 | 3.04 (2) | 170 |
O4W—H4WB···O3W | 0.85 | 2.08 | 2.921 (10) | 168 |
O5W—H5WA···O3W | 0.85 | 2.32 | 2.88 (4) | 124 |
O5W—H5WB···O5Wi | 0.85 | 1.97 | 2.48 (7) | 118 |
O6W—H6WA···O3vi | 0.85 | 2.06 | 2.90 (2) | 175 |
Symmetry codes: (i) −x+2, y, −z+1/2; (ii) −x+3/2, −y+3/2, −z+1; (iii) −x+3/2, y+1/2, −z+1/2; (iv) x+1/2, −y+3/2, z+1/2; (v) −x+3/2, y−1/2, −z+1/2; (vi) x, −y+1, z−1/2; (vii) −x+2, −y+1, −z+1. |