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The title compound was obtained by the condensation of ethyl­enedi­amine and (5E,5E,6Z,6Z)-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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023001895/zv2022sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023001895/zv2022Isup3.hkl
Contains datablock I

CCDC reference: 2153643

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](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

Computing details top

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).

(5E,5'E,6Z,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
C30H34F2N6O2·2.5H2OF(000) = 3780
Mr = 593.67Dx = 1.267 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 22.7715 (19) ÅCell parameters from 2620 reflections
b = 17.2794 (15) Åθ = 2.5–18.8°
c = 25.640 (3) ŵ = 0.10 mm1
β = 112.297 (1)°T = 296 K
V = 9334.2 (16) Å3Prism, colourless
Z = 120.16 × 0.14 × 0.11 mm
Data collection top
Bruker APEXII CCD
diffractometer
Rint = 0.070
φ and ω scansθmax = 25.1°, θmin = 1.9°
37069 measured reflectionsh = 2727
8249 independent reflectionsk = 2020
4099 reflections with I > 2σ(I)l = 3030
Refinement top
Refinement on F225 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.058H-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 reflectionsΔρmax = 0.20 e Å3
601 parametersΔρmin = 0.29 e Å3
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
xyzUiso*/UeqOcc. (<1)
F21.09554 (9)0.57702 (14)0.53005 (9)0.0952 (7)
O60.89907 (11)0.85004 (13)0.36530 (9)0.0707 (7)
N90.95271 (11)0.63828 (14)0.27726 (10)0.0497 (6)
H90.9147060.6389970.2522260.060*
F30.76710 (10)0.32116 (12)0.48211 (10)0.1025 (8)
N100.86237 (11)0.75960 (14)0.27290 (10)0.0519 (6)
N20.75280 (11)0.67741 (14)0.31652 (10)0.0521 (6)
H20.7913520.6772510.3405270.063*
N30.78027 (11)0.76386 (14)0.41673 (10)0.0530 (7)
H30.7710480.7157920.4179040.064*
N10.84455 (11)0.71070 (15)0.23249 (10)0.0539 (7)
N70.83957 (12)0.55075 (15)0.32396 (11)0.0557 (7)
N60.85905 (12)0.60375 (15)0.36126 (11)0.0550 (7)
N40.82821 (12)0.67186 (16)0.51854 (11)0.0588 (7)
O70.79621 (12)0.44357 (15)0.24172 (11)0.0846 (8)
N50.79668 (12)0.63644 (15)0.47308 (11)0.0581 (7)
F40.60711 (11)0.74370 (16)0.06565 (10)0.1250 (9)
O30.89386 (14)0.75091 (17)0.61336 (10)0.0977 (9)
C120.96907 (13)0.69768 (16)0.31285 (11)0.0446 (7)
C70.92362 (13)0.75336 (17)0.31220 (12)0.0460 (7)
C80.93933 (15)0.80892 (17)0.35815 (12)0.0492 (7)
C200.73494 (14)0.61741 (17)0.28199 (12)0.0499 (8)
C101.05603 (13)0.78558 (17)0.37729 (12)0.0509 (8)
C130.99160 (14)0.57224 (16)0.27573 (12)0.0514 (8)
H13A0.9688910.5249590.2762940.062*
H13B1.0303490.5728080.3092100.062*
C111.03605 (13)0.70393 (17)0.35377 (12)0.0498 (7)
H11A1.0639500.6868570.3353690.060*
H11B1.0419150.6690600.3850020.060*
C400.92104 (14)0.59354 (18)0.40252 (13)0.0524 (8)
C210.77828 (15)0.55750 (17)0.28450 (13)0.0526 (8)
C310.83760 (14)0.75046 (19)0.51517 (12)0.0538 (8)
C260.81638 (13)0.79584 (17)0.46495 (13)0.0506 (8)
C40.78281 (14)0.72419 (19)0.19112 (12)0.0523 (8)
C340.79058 (14)0.55572 (19)0.47871 (14)0.0556 (8)
C390.76263 (15)0.5143 (2)0.42909 (14)0.0607 (9)
H390.7495490.5401460.3947190.073*
C250.75416 (15)0.80125 (18)0.36141 (12)0.0580 (8)
H25A0.7884410.8195370.3509190.070*
H25B0.7285650.8454380.3628860.070*
C240.71388 (14)0.74392 (18)0.31816 (12)0.0559 (8)
H24A0.6787420.7269860.3279340.067*
H24B0.6966460.7682550.2813440.067*
C91.00665 (14)0.81378 (18)0.39906 (12)0.0544 (8)
H9A1.0106640.7838190.4322370.065*
H9B1.0159340.8672630.4107730.065*
C220.75933 (17)0.4957 (2)0.24298 (14)0.0634 (9)
C450.96325 (16)0.53591 (19)0.40083 (14)0.0595 (9)
H450.9516410.5007970.3711370.071*
C410.93867 (14)0.64476 (19)0.44682 (14)0.0581 (8)
H410.9105660.6833240.4477030.070*
C350.80994 (15)0.5166 (2)0.53017 (14)0.0626 (9)
H350.8285540.5435800.5638350.075*
C360.80127 (16)0.4373 (2)0.53080 (17)0.0724 (10)
H360.8137230.4104940.5647560.087*
C441.02267 (16)0.5316 (2)0.44389 (16)0.0675 (10)
H441.0516750.4941830.4431130.081*
C190.66830 (15)0.61617 (18)0.23968 (13)0.0621 (9)
H19A0.6656240.6494030.2083680.075*
H19B0.6406370.6376500.2569040.075*
C431.03795 (16)0.5828 (2)0.48728 (16)0.0666 (10)
C300.87277 (17)0.7878 (2)0.56849 (15)0.0678 (9)
C280.89082 (16)0.90513 (19)0.51674 (14)0.0659 (9)
C270.83332 (15)0.87873 (17)0.46489 (13)0.0607 (9)
H27A0.7968960.9097880.4624710.073*
H27B0.8420910.8889470.4313520.073*
C180.64399 (16)0.5357 (2)0.21674 (14)0.0680 (10)
C380.75398 (16)0.4358 (2)0.42995 (16)0.0693 (10)
H380.7347670.4083620.3965380.083*
C420.99769 (16)0.6397 (2)0.49014 (14)0.0666 (9)
H421.0095720.6740410.5203100.080*
C30.74440 (16)0.7869 (2)0.19078 (14)0.0655 (9)
H3A0.7586770.8242480.2188970.079*
C50.76179 (16)0.6708 (2)0.14840 (14)0.0672 (9)
H50.7878440.6293390.1483300.081*
C151.06016 (17)0.83952 (19)0.33173 (14)0.0701 (10)
H15A1.0888260.8181250.3161150.105*
H15B1.0754070.8892480.3479160.105*
H15C1.0188410.8451620.3024900.105*
C290.88290 (17)0.8731 (2)0.56898 (14)0.0710 (10)
H29A0.9204470.8860390.6017200.085*
H29B0.8470520.8987160.5731980.085*
C370.77395 (16)0.3988 (2)0.48037 (19)0.0713 (10)
C230.69345 (16)0.4967 (2)0.19936 (14)0.0726 (10)
H23A0.6802410.4437260.1887600.087*
H23B0.6942560.5228010.1661310.087*
C141.12089 (15)0.7801 (2)0.42564 (14)0.0742 (10)
H14A1.1181890.7457580.4540650.111*
H14B1.1336610.8305530.4416400.111*
H14C1.1515420.7606390.4115750.111*
C460.66604 (18)0.7378 (3)0.10724 (16)0.0812 (11)
C60.70266 (19)0.6772 (3)0.10544 (15)0.0791 (11)
H60.6886390.6411510.0763800.095*
C330.95173 (17)0.8743 (2)0.51310 (16)0.0831 (11)
H33A0.9492590.8189390.5095100.125*
H33B0.9871620.8881380.5466440.125*
H33C0.9571990.8962370.4808480.125*
C170.63175 (18)0.4872 (2)0.26157 (17)0.0875 (12)
H17A0.6706400.4811960.2937640.131*
H17B0.6160020.4371810.2463230.131*
H17C0.6009460.5127640.2727250.131*
C20.68508 (18)0.7934 (2)0.14860 (16)0.0795 (11)
H2A0.6585180.8344470.1481600.095*
C160.58150 (18)0.5454 (2)0.16554 (17)0.0996 (14)
H16A0.5504010.5691130.1772590.149*
H16B0.5664890.4955460.1494300.149*
H16C0.5885580.5775060.1379320.149*
C320.8926 (2)0.9931 (2)0.51835 (18)0.0964 (13)
H32A0.8967501.0124110.4847910.145*
H32B0.9281801.0100590.5507790.145*
H32C0.8540801.0124470.5205020.145*
O2W0.85971 (16)0.5119 (2)0.17268 (14)0.1381 (12)
H2WA0.8408830.4931440.1927780.207*
H2WB0.8791230.4737040.1657980.207*
O1W0.93443 (17)0.6011 (2)0.65403 (17)0.1587 (15)
H1WA0.9705800.6206510.6727850.238*
H1WB0.9101300.6399510.6418470.238*
O3W0.92308 (17)0.3840 (2)0.2815 (2)0.1847 (19)
H3WA0.9359320.3383460.2793480.277*
H3WB0.8828920.3800270.2691880.277*
O4W0.9769 (4)0.2282 (5)0.2984 (4)0.180 (3)0.5
H4WA0.9851400.2270730.2687240.270*0.5
H4WB0.9626010.2735030.2988950.270*0.5
O5W0.9411 (16)0.241 (2)0.2313 (14)0.175 (4)0.125
H5WA0.9110130.2657070.2360690.263*0.125
H5WB0.9698130.2753970.2365990.263*0.125
O6W0.9656 (16)0.1682 (18)0.2174 (11)0.152 (11)0.125
H6WA0.9429590.1926820.1878850.229*0.125
H6WB0.9496690.1230320.2128350.229*0.125
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F20.0492 (12)0.1286 (19)0.0893 (15)0.0052 (12)0.0055 (12)0.0275 (14)
O60.0634 (15)0.0765 (16)0.0659 (15)0.0190 (13)0.0174 (12)0.0113 (12)
N90.0451 (14)0.0494 (15)0.0520 (15)0.0007 (12)0.0157 (12)0.0013 (13)
F30.0878 (16)0.0592 (13)0.133 (2)0.0079 (11)0.0110 (14)0.0246 (13)
N100.0481 (16)0.0540 (16)0.0504 (16)0.0013 (13)0.0153 (14)0.0014 (13)
N20.0465 (15)0.0554 (16)0.0465 (15)0.0008 (13)0.0088 (12)0.0035 (13)
N30.0575 (16)0.0460 (15)0.0480 (15)0.0019 (12)0.0114 (13)0.0015 (12)
N10.0471 (16)0.0600 (17)0.0506 (16)0.0003 (13)0.0141 (14)0.0011 (14)
N70.0548 (17)0.0560 (17)0.0556 (16)0.0069 (13)0.0200 (15)0.0017 (14)
N60.0489 (16)0.0614 (17)0.0512 (16)0.0062 (13)0.0150 (14)0.0006 (14)
N40.0586 (17)0.0617 (19)0.0545 (17)0.0017 (14)0.0194 (14)0.0029 (14)
O70.0789 (18)0.0724 (17)0.100 (2)0.0005 (14)0.0314 (16)0.0241 (15)
N50.0596 (17)0.0575 (18)0.0527 (17)0.0005 (14)0.0162 (14)0.0002 (14)
F40.0794 (16)0.154 (2)0.0920 (17)0.0178 (15)0.0236 (14)0.0128 (16)
O30.123 (2)0.098 (2)0.0496 (15)0.0072 (17)0.0072 (16)0.0027 (15)
C120.0480 (18)0.0432 (18)0.0428 (17)0.0026 (14)0.0174 (15)0.0015 (14)
C70.0442 (18)0.0466 (17)0.0447 (17)0.0040 (14)0.0141 (15)0.0048 (14)
C80.0532 (19)0.0493 (18)0.0453 (18)0.0078 (16)0.0189 (16)0.0036 (15)
C200.0531 (19)0.0517 (19)0.0415 (17)0.0090 (16)0.0143 (15)0.0034 (15)
C100.0459 (18)0.0524 (19)0.0500 (18)0.0059 (15)0.0134 (15)0.0055 (15)
C130.0559 (19)0.0392 (16)0.0572 (19)0.0019 (15)0.0193 (16)0.0004 (14)
C110.0439 (18)0.0504 (18)0.0518 (18)0.0026 (15)0.0146 (15)0.0012 (15)
C400.0451 (19)0.056 (2)0.056 (2)0.0016 (16)0.0188 (17)0.0053 (16)
C210.0502 (19)0.0482 (19)0.056 (2)0.0041 (16)0.0163 (17)0.0007 (16)
C310.0536 (19)0.060 (2)0.0438 (18)0.0015 (16)0.0141 (16)0.0051 (16)
C260.0447 (18)0.0520 (19)0.055 (2)0.0034 (15)0.0194 (16)0.0079 (16)
C40.0476 (19)0.065 (2)0.0389 (17)0.0007 (17)0.0104 (15)0.0049 (16)
C340.0494 (19)0.057 (2)0.061 (2)0.0031 (16)0.0225 (17)0.0116 (17)
C390.058 (2)0.062 (2)0.056 (2)0.0010 (17)0.0154 (17)0.0074 (18)
C250.062 (2)0.0522 (19)0.0497 (19)0.0048 (16)0.0101 (17)0.0060 (16)
C240.0528 (19)0.057 (2)0.0486 (18)0.0060 (16)0.0086 (16)0.0040 (16)
C90.057 (2)0.0558 (19)0.0472 (18)0.0013 (16)0.0162 (16)0.0041 (15)
C220.067 (2)0.056 (2)0.065 (2)0.0082 (19)0.023 (2)0.0040 (18)
C450.061 (2)0.061 (2)0.061 (2)0.0007 (18)0.0274 (19)0.0072 (17)
C410.0442 (19)0.060 (2)0.065 (2)0.0024 (16)0.0155 (18)0.0031 (18)
C350.057 (2)0.074 (2)0.056 (2)0.0042 (18)0.0200 (17)0.0082 (18)
C360.062 (2)0.072 (3)0.079 (3)0.003 (2)0.022 (2)0.030 (2)
C440.051 (2)0.071 (2)0.084 (3)0.0148 (18)0.028 (2)0.024 (2)
C190.054 (2)0.062 (2)0.056 (2)0.0027 (16)0.0051 (17)0.0009 (17)
C430.044 (2)0.082 (3)0.066 (2)0.002 (2)0.0114 (19)0.021 (2)
C300.067 (2)0.077 (3)0.055 (2)0.006 (2)0.0184 (19)0.005 (2)
C280.065 (2)0.061 (2)0.066 (2)0.0066 (18)0.0187 (19)0.0158 (18)
C270.064 (2)0.053 (2)0.061 (2)0.0050 (16)0.0187 (18)0.0070 (16)
C180.057 (2)0.067 (2)0.063 (2)0.0098 (18)0.0033 (18)0.0026 (18)
C380.062 (2)0.062 (2)0.072 (2)0.0038 (18)0.013 (2)0.004 (2)
C420.052 (2)0.075 (2)0.065 (2)0.0087 (19)0.0135 (19)0.0012 (19)
C30.067 (2)0.068 (2)0.055 (2)0.0049 (19)0.0147 (19)0.0068 (17)
C50.060 (2)0.081 (2)0.054 (2)0.0016 (19)0.0142 (19)0.0019 (19)
C150.079 (2)0.058 (2)0.081 (2)0.0153 (18)0.039 (2)0.0003 (19)
C290.073 (2)0.076 (3)0.057 (2)0.006 (2)0.0171 (19)0.0179 (19)
C370.054 (2)0.055 (2)0.095 (3)0.0012 (18)0.017 (2)0.009 (2)
C230.075 (3)0.065 (2)0.067 (2)0.009 (2)0.014 (2)0.0092 (18)
C140.057 (2)0.077 (3)0.077 (2)0.0035 (19)0.0117 (19)0.016 (2)
C460.061 (2)0.102 (3)0.058 (2)0.002 (2)0.004 (2)0.012 (2)
C60.072 (3)0.095 (3)0.052 (2)0.005 (2)0.004 (2)0.005 (2)
C330.063 (2)0.104 (3)0.077 (3)0.010 (2)0.021 (2)0.019 (2)
C170.077 (3)0.082 (3)0.098 (3)0.018 (2)0.027 (2)0.005 (2)
C20.070 (3)0.085 (3)0.076 (3)0.024 (2)0.018 (2)0.020 (2)
C160.075 (3)0.091 (3)0.091 (3)0.010 (2)0.016 (2)0.018 (2)
C320.118 (4)0.063 (3)0.099 (3)0.015 (2)0.031 (3)0.025 (2)
O2W0.137 (3)0.153 (3)0.134 (3)0.008 (2)0.062 (2)0.002 (2)
O1W0.130 (3)0.116 (3)0.188 (4)0.014 (2)0.013 (3)0.049 (2)
O3W0.111 (3)0.134 (3)0.298 (6)0.003 (2)0.066 (3)0.025 (3)
O4W0.160 (6)0.137 (6)0.170 (6)0.040 (5)0.019 (5)0.015 (5)
O5W0.157 (7)0.138 (7)0.166 (7)0.038 (6)0.011 (6)0.015 (6)
O6W0.19 (3)0.13 (2)0.12 (2)0.05 (2)0.05 (2)0.050 (18)
Geometric parameters (Å, º) top
F2—C431.357 (4)C36—C371.375 (5)
O6—C81.227 (3)C36—H360.9300
N9—C121.329 (3)C44—C431.360 (5)
N9—C131.454 (4)C44—H440.9300
N9—H90.8600C19—C181.529 (4)
F3—C371.353 (4)C19—H19A0.9700
N10—N11.278 (3)C19—H19B0.9700
N10—C71.380 (3)C43—C421.365 (5)
N2—C201.323 (3)C30—C291.491 (5)
N2—C241.461 (4)C28—C321.521 (5)
N2—H20.8600C28—C331.522 (5)
N3—C261.319 (3)C28—C291.522 (5)
N3—C251.464 (3)C28—C271.539 (4)
N3—H30.8600C27—H27A0.9700
N1—C41.423 (4)C27—H27B0.9700
N7—N61.276 (3)C18—C231.517 (5)
N7—C211.383 (4)C18—C171.531 (5)
N6—C401.418 (4)C18—C161.536 (4)
N4—N51.270 (3)C38—C371.357 (5)
N4—C311.383 (4)C38—H380.9300
O7—C221.240 (4)C42—H420.9300
N5—C341.414 (4)C3—C21.378 (5)
F4—C461.365 (4)C3—H3A0.9300
O3—C301.242 (4)C5—C61.383 (5)
C12—C71.409 (4)C5—H50.9300
C12—C111.491 (4)C15—H15A0.9600
C7—C81.455 (4)C15—H15B0.9600
C8—C91.496 (4)C15—H15C0.9600
C20—C211.415 (4)C29—H29A0.9700
C20—C191.494 (4)C29—H29B0.9700
C10—C91.513 (4)C23—H23A0.9700
C10—C151.525 (4)C23—H23B0.9700
C10—C141.529 (4)C14—H14A0.9600
C10—C111.534 (4)C14—H14B0.9600
C13—C13i1.507 (6)C14—H14C0.9600
C13—H13A0.9700C46—C61.350 (5)
C13—H13B0.9700C46—C21.373 (5)
C11—H11A0.9700C6—H60.9300
C11—H11B0.9700C33—H33A0.9600
C40—C411.374 (4)C33—H33B0.9600
C40—C451.396 (4)C33—H33C0.9600
C21—C221.453 (4)C17—H17A0.9600
C31—C261.426 (4)C17—H17B0.9600
C31—C301.448 (4)C17—H17C0.9600
C26—C271.483 (4)C2—H2A0.9300
C4—C51.372 (4)C16—H16A0.9600
C4—C31.390 (4)C16—H16B0.9600
C34—C391.386 (4)C16—H16C0.9600
C34—C351.397 (4)C32—H32A0.9600
C39—C381.374 (4)C32—H32B0.9600
C39—H390.9300C32—H32C0.9600
C25—C241.510 (4)O2W—H2WA0.8500
C25—H25A0.9700O2W—H2WB0.8497
C25—H25B0.9700O1W—H1WA0.8499
C24—H24A0.9700O1W—H1WB0.8500
C24—H24B0.9700O3W—H3WA0.8500
C9—H9A0.9700O3W—H3WB0.8500
C9—H9B0.9700O4W—H4WA0.8503
C22—C231.493 (4)O4W—H4WB0.8499
C45—C441.386 (4)O5W—H5WA0.8501
C45—H450.9300O5W—H5WB0.8501
C41—C421.384 (4)O6W—O6Wi1.80 (6)
C41—H410.9300O6W—H6WA0.8499
C35—C361.385 (5)O6W—H6WB0.8500
C35—H350.9300
C12—N9—C13127.6 (3)C18—C19—H19B108.7
C12—N9—H9116.2H19A—C19—H19B107.6
C13—N9—H9116.2F2—C43—C44118.8 (3)
N1—N10—C7117.5 (2)F2—C43—C42118.2 (4)
C20—N2—C24126.8 (3)C44—C43—C42123.0 (3)
C20—N2—H2116.6O3—C30—C31121.8 (3)
C24—N2—H2116.6O3—C30—C29119.7 (3)
C26—N3—C25127.1 (3)C31—C30—C29118.5 (3)
C26—N3—H3116.5C32—C28—C33109.7 (3)
C25—N3—H3116.5C32—C28—C29110.5 (3)
N10—N1—C4114.6 (3)C33—C28—C29110.0 (3)
N6—N7—C21117.1 (3)C32—C28—C27109.0 (3)
N7—N6—C40115.8 (3)C33—C28—C27109.9 (3)
N5—N4—C31117.6 (3)C29—C28—C27107.8 (3)
N4—N5—C34115.1 (3)C26—C27—C28114.9 (3)
N9—C12—C7120.4 (3)C26—C27—H27A108.5
N9—C12—C11119.0 (3)C28—C27—H27A108.5
C7—C12—C11120.6 (3)C26—C27—H27B108.5
N10—C7—C12126.6 (3)C28—C27—H27B108.5
N10—C7—C8114.2 (3)H27A—C27—H27B107.5
C12—C7—C8119.2 (3)C23—C18—C19108.4 (3)
O6—C8—C7122.3 (3)C23—C18—C17110.1 (3)
O6—C8—C9119.2 (3)C19—C18—C17110.6 (3)
C7—C8—C9118.5 (3)C23—C18—C16110.3 (3)
N2—C20—C21120.7 (3)C19—C18—C16108.2 (3)
N2—C20—C19117.8 (3)C17—C18—C16109.1 (3)
C21—C20—C19121.4 (3)C37—C38—C39118.9 (3)
C9—C10—C15110.9 (3)C37—C38—H38120.6
C9—C10—C14110.2 (2)C39—C38—H38120.6
C15—C10—C14109.7 (3)C43—C42—C41118.0 (3)
C9—C10—C11106.8 (2)C43—C42—H42121.0
C15—C10—C11110.9 (2)C41—C42—H42121.0
C14—C10—C11108.3 (2)C2—C3—C4119.7 (3)
N9—C13—C13i112.5 (2)C2—C3—H3A120.1
N9—C13—H13A109.1C4—C3—H3A120.1
C13i—C13—H13A109.1C4—C5—C6121.4 (3)
N9—C13—H13B109.1C4—C5—H5119.3
C13i—C13—H13B109.1C6—C5—H5119.3
H13A—C13—H13B107.8C10—C15—H15A109.5
C12—C11—C10114.5 (2)C10—C15—H15B109.5
C12—C11—H11A108.6H15A—C15—H15B109.5
C10—C11—H11A108.6C10—C15—H15C109.5
C12—C11—H11B108.6H15A—C15—H15C109.5
C10—C11—H11B108.6H15B—C15—H15C109.5
H11A—C11—H11B107.6C30—C29—C28114.9 (3)
C41—C40—C45119.8 (3)C30—C29—H29A108.5
C41—C40—N6115.6 (3)C28—C29—H29A108.5
C45—C40—N6124.6 (3)C30—C29—H29B108.5
N7—C21—C20126.0 (3)C28—C29—H29B108.5
N7—C21—C22114.2 (3)H29A—C29—H29B107.5
C20—C21—C22119.8 (3)F3—C37—C38119.8 (4)
N4—C31—C26126.1 (3)F3—C37—C36117.7 (4)
N4—C31—C30115.0 (3)C38—C37—C36122.5 (3)
C26—C31—C30118.9 (3)C22—C23—C18115.6 (3)
N3—C26—C31119.6 (3)C22—C23—H23A108.4
N3—C26—C27118.3 (3)C18—C23—H23A108.4
C31—C26—C27122.2 (3)C22—C23—H23B108.4
C5—C4—C3119.4 (3)C18—C23—H23B108.4
C5—C4—N1115.6 (3)H23A—C23—H23B107.4
C3—C4—N1125.0 (3)C10—C14—H14A109.5
C39—C34—C35119.2 (3)C10—C14—H14B109.5
C39—C34—N5116.3 (3)H14A—C14—H14B109.5
C35—C34—N5124.5 (3)C10—C14—H14C109.5
C38—C39—C34120.9 (3)H14A—C14—H14C109.5
C38—C39—H39119.5H14B—C14—H14C109.5
C34—C39—H39119.5C6—C46—F4117.9 (4)
N3—C25—C24109.4 (2)C6—C46—C2123.4 (3)
N3—C25—H25A109.8F4—C46—C2118.7 (4)
C24—C25—H25A109.8C46—C6—C5117.6 (4)
N3—C25—H25B109.8C46—C6—H6121.2
C24—C25—H25B109.8C5—C6—H6121.2
H25A—C25—H25B108.2C28—C33—H33A109.5
N2—C24—C25109.3 (2)C28—C33—H33B109.5
N2—C24—H24A109.8H33A—C33—H33B109.5
C25—C24—H24A109.8C28—C33—H33C109.5
N2—C24—H24B109.8H33A—C33—H33C109.5
C25—C24—H24B109.8H33B—C33—H33C109.5
H24A—C24—H24B108.3C18—C17—H17A109.5
C8—C9—C10115.5 (2)C18—C17—H17B109.5
C8—C9—H9A108.4H17A—C17—H17B109.5
C10—C9—H9A108.4C18—C17—H17C109.5
C8—C9—H9B108.4H17A—C17—H17C109.5
C10—C9—H9B108.4H17B—C17—H17C109.5
H9A—C9—H9B107.5C46—C2—C3118.5 (4)
O7—C22—C21122.5 (3)C46—C2—H2A120.7
O7—C22—C23119.2 (3)C3—C2—H2A120.7
C21—C22—C23118.3 (3)C18—C16—H16A109.5
C44—C45—C40119.3 (3)C18—C16—H16B109.5
C44—C45—H45120.4H16A—C16—H16B109.5
C40—C45—H45120.4C18—C16—H16C109.5
C40—C41—C42120.9 (3)H16A—C16—H16C109.5
C40—C41—H41119.6H16B—C16—H16C109.5
C42—C41—H41119.6C28—C32—H32A109.5
C36—C35—C34119.7 (3)C28—C32—H32B109.5
C36—C35—H35120.2H32A—C32—H32B109.5
C34—C35—H35120.2C28—C32—H32C109.5
C37—C36—C35118.9 (3)H32A—C32—H32C109.5
C37—C36—H36120.6H32B—C32—H32C109.5
C35—C36—H36120.6H2WA—O2W—H2WB104.5
C43—C44—C45119.1 (3)H1WA—O1W—H1WB104.5
C43—C44—H44120.5H3WA—O3W—H3WB104.5
C45—C44—H44120.5H4WA—O4W—H4WB104.5
C20—C19—C18114.3 (3)H5WA—O5W—H5WB104.5
C20—C19—H19A108.7O6Wi—O6W—H6WA147.7
C18—C19—H19A108.7O6Wi—O6W—H6WB107.6
C20—C19—H19B108.7H6WA—O6W—H6WB104.5
C7—N10—N1—C4175.2 (2)N7—C21—C22—C23178.6 (3)
C21—N7—N6—C40177.4 (2)C20—C21—C22—C231.3 (4)
C31—N4—N5—C34177.7 (3)C41—C40—C45—C440.4 (4)
C13—N9—C12—C7173.7 (2)N6—C40—C45—C44179.7 (3)
C13—N9—C12—C115.7 (4)C45—C40—C41—C420.5 (5)
N1—N10—C7—C120.6 (4)N6—C40—C41—C42178.9 (3)
N1—N10—C7—C8177.4 (2)C39—C34—C35—C360.4 (5)
N9—C12—C7—N108.4 (4)N5—C34—C35—C36179.5 (3)
C11—C12—C7—N10172.2 (3)C34—C35—C36—C370.4 (5)
N9—C12—C7—C8168.2 (2)C40—C45—C44—C431.2 (5)
C11—C12—C7—C811.2 (4)N2—C20—C19—C18158.9 (3)
N10—C7—C8—O69.6 (4)C21—C20—C19—C1822.5 (4)
C12—C7—C8—O6167.4 (3)C45—C44—C43—F2178.3 (3)
N10—C7—C8—C9172.5 (2)C45—C44—C43—C421.1 (5)
C12—C7—C8—C910.4 (4)N4—C31—C30—O31.6 (5)
C24—N2—C20—C21178.8 (3)C26—C31—C30—O3178.1 (3)
C24—N2—C20—C190.2 (4)N4—C31—C30—C29177.7 (3)
C12—N9—C13—C13i111.6 (3)C26—C31—C30—C292.7 (5)
N9—C12—C11—C10159.0 (3)N3—C26—C27—C28161.6 (3)
C7—C12—C11—C1021.6 (4)C31—C26—C27—C2818.7 (4)
C9—C10—C11—C1251.5 (3)C32—C28—C27—C26166.1 (3)
C15—C10—C11—C1269.4 (3)C33—C28—C27—C2673.8 (4)
C14—C10—C11—C12170.2 (3)C29—C28—C27—C2646.1 (4)
N7—N6—C40—C41171.5 (3)C20—C19—C18—C2348.5 (4)
N7—N6—C40—C457.8 (4)C20—C19—C18—C1772.4 (4)
N6—N7—C21—C200.6 (4)C20—C19—C18—C16168.1 (3)
N6—N7—C21—C22179.5 (3)C34—C39—C38—C370.7 (5)
N2—C20—C21—N75.5 (5)F2—C43—C42—C41179.1 (3)
C19—C20—C21—N7175.9 (3)C44—C43—C42—C410.3 (5)
N2—C20—C21—C22174.6 (3)C40—C41—C42—C430.5 (5)
C19—C20—C21—C224.0 (4)C5—C4—C3—C21.9 (5)
N5—N4—C31—C261.5 (5)N1—C4—C3—C2179.4 (3)
N5—N4—C31—C30178.8 (3)C3—C4—C5—C61.1 (5)
C25—N3—C26—C31179.9 (3)N1—C4—C5—C6179.9 (3)
C25—N3—C26—C270.1 (4)O3—C30—C29—C28146.9 (3)
N4—C31—C26—N35.5 (5)C31—C30—C29—C2833.8 (4)
C30—C31—C26—N3174.9 (3)C32—C28—C29—C30173.0 (3)
N4—C31—C26—C27174.8 (3)C33—C28—C29—C3065.8 (4)
C30—C31—C26—C274.8 (4)C27—C28—C29—C3054.0 (4)
N10—N1—C4—C5177.7 (3)C39—C38—C37—F3178.6 (3)
N10—N1—C4—C33.6 (4)C39—C38—C37—C361.5 (5)
N4—N5—C34—C39173.0 (3)C35—C36—C37—F3178.8 (3)
N4—N5—C34—C357.8 (4)C35—C36—C37—C381.3 (5)
C35—C34—C39—C380.2 (5)O7—C22—C23—C18153.5 (3)
N5—C34—C39—C38179.4 (3)C21—C22—C23—C1828.2 (5)
C26—N3—C25—C24178.3 (3)C19—C18—C23—C2251.9 (4)
C20—N2—C24—C25176.4 (3)C17—C18—C23—C2269.2 (4)
N3—C25—C24—N259.1 (3)C16—C18—C23—C22170.2 (3)
O6—C8—C9—C10158.5 (3)F4—C46—C6—C5178.7 (3)
C7—C8—C9—C1023.6 (4)C2—C46—C6—C51.3 (6)
C15—C10—C9—C868.3 (3)C4—C5—C6—C460.5 (5)
C14—C10—C9—C8170.0 (3)C6—C46—C2—C30.5 (6)
C11—C10—C9—C852.6 (3)F4—C46—C2—C3179.5 (3)
N7—C21—C22—O73.2 (5)C4—C3—C2—C461.2 (5)
C20—C21—C22—O7176.8 (3)
Symmetry code: (i) x+2, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N9—H9···N10.861.932.609 (3)135
N2—H2···N60.861.912.585 (3)134
N3—H3···N50.861.902.582 (3)136
C13—H13B···O2Wi0.972.593.302 (4)130
C25—H25A···O60.972.463.370 (4)156
C24—H24A···O3ii0.972.653.518 (4)149
C24—H24A···O5Wiii0.972.583.27 (4)128
C27—H27B···O60.972.583.451 (4)149
C42—H42···F4iv0.932.523.218 (4)132
C5—H5···O2W0.932.533.441 (5)166
C23—H23A···O6v0.972.433.311 (4)151
O2W—H2WA···O70.852.082.926 (4)178
O2W—H2WB···O1Wvi0.851.912.749 (5)171
O1W—H1WA···O3Wvii0.852.263.042 (5)154
O1W—H1WB···O30.852.032.812 (4)152
O3W—H3WA···O4W0.852.092.921 (10)164
O3W—H3WA···O5W0.852.112.88 (4)151
O3W—H3WB···O70.852.132.866 (4)144
O4W—H4WA···O4Wi0.852.203.04 (2)170
O4W—H4WB···O3W0.852.082.921 (10)168
O5W—H5WA···O3W0.852.322.88 (4)124
O5W—H5WB···O5Wi0.851.972.48 (7)118
O6W—H6WA···O3vi0.852.062.90 (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, y1/2, z+1/2; (vi) x, y+1, z1/2; (vii) x+2, y+1, z+1.
 

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