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The supra­molecular assemblies of the two title structures are one-dimensional: the chain-of-rings motifs are supported by aromatic π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989022011501/vm2275sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989022011501/vm2275Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989022011501/vm2275IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989022011501/vm2275Isup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989022011501/vm2275IIsup5.cml
Supplementary material

CCDC references: 2223441; 2223442

Computing details top

For both structures, data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/2 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

4-(4-Nitrophenyl)piperazin-1-ium trifluoroacetate (I) top
Crystal data top
C10H14N3O2+·C2F3O2F(000) = 664
Mr = 321.26Dx = 1.542 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 6.6889 (4) ÅCell parameters from 2766 reflections
b = 18.376 (1) Åθ = 2.9–27.8°
c = 11.2600 (7) ŵ = 0.14 mm1
β = 91.131 (6)°T = 293 K
V = 1383.76 (14) Å3Prism, yellow
Z = 40.50 × 0.44 × 0.44 mm
Data collection top
Oxford Diffraction Xcalibur with Sapphire CCD
diffractometer
1908 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.020
Rotation method data acquisition using ω scans.θmax = 25.3°, θmin = 2.9°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction (2009)
h = 87
Tmin = 0.784, Tmax = 1.000k = 1722
4855 measured reflectionsl = 1113
2515 independent reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.0484P)2 + 0.5034P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.106(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.28 e Å3
2515 reflectionsΔρmin = 0.28 e Å3
239 parametersExtinction correction: SHELXL2019/2 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
84 restraintsExtinction coefficient: 0.053 (3)
Primary atom site location: structure-invariant direct methods
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)
O10.6694 (3)0.05792 (11)0.27331 (14)0.0805 (6)
O20.6790 (2)0.05336 (10)0.21928 (14)0.0636 (5)
N10.8545 (2)0.10090 (8)0.26900 (12)0.0356 (4)
N20.6570 (2)0.12077 (8)0.48752 (13)0.0312 (4)
N30.6925 (2)0.01145 (11)0.19696 (15)0.0476 (5)
C10.8114 (2)0.07873 (10)0.15542 (15)0.0312 (4)
C20.8000 (3)0.12928 (11)0.06160 (16)0.0419 (5)
H20.8188590.1785010.0774330.050*
C30.7615 (3)0.10711 (12)0.05228 (17)0.0447 (5)
H30.7539870.1411710.1132940.054*
C40.7339 (3)0.03448 (11)0.07686 (15)0.0365 (4)
C50.7466 (2)0.01673 (11)0.01221 (16)0.0377 (4)
H50.7299930.0658480.0052340.045*
C60.7840 (3)0.00528 (10)0.12678 (16)0.0355 (4)
H60.7913710.0294000.1868600.043*
C70.8875 (3)0.05084 (10)0.36718 (15)0.0341 (4)
H7A1.0015620.0669790.4147940.041*
H7B0.9174670.0028450.3363920.041*
C80.7060 (3)0.04672 (9)0.44371 (15)0.0320 (4)
H8A0.5937790.0273240.3979460.038*
H8B0.7322010.0145040.5104610.038*
C90.6318 (3)0.17363 (10)0.38863 (16)0.0373 (4)
H9A0.6102170.2219630.4205500.045*
H9B0.5157210.1605350.3402490.045*
C100.8162 (3)0.17372 (10)0.31302 (16)0.0401 (5)
H10A0.7967620.2067850.2466410.048*
H10B0.9303520.1905040.3598620.048*
C110.1577 (3)0.17011 (10)0.61221 (17)0.0386 (5)
C12A0.2811 (6)0.2193 (2)0.6965 (3)0.0574 (11)0.779 (4)
C12B0.295 (2)0.2305 (8)0.6565 (13)0.0574 (11)0.221 (4)
O30.2518 (2)0.12351 (8)0.55930 (14)0.0522 (4)
O40.0240 (2)0.18168 (9)0.61548 (14)0.0593 (5)
F1A0.4768 (4)0.22180 (19)0.6652 (3)0.0873 (11)0.779 (4)
F2A0.2265 (4)0.28753 (13)0.6917 (4)0.0974 (13)0.779 (4)
F3A0.2611 (5)0.2012 (2)0.8079 (2)0.1261 (13)0.779 (4)
F1B0.2251 (14)0.2549 (8)0.7591 (12)0.089 (3)0.221 (4)
F2B0.4517 (17)0.1991 (8)0.7164 (11)0.090 (3)0.221 (4)
F3B0.2926 (17)0.2875 (5)0.5852 (13)0.129 (3)0.221 (4)
H210.541 (3)0.1200 (11)0.5272 (17)0.047 (6)*
H220.752 (2)0.1340 (10)0.5372 (15)0.038 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1184 (16)0.0917 (14)0.0310 (8)0.0055 (11)0.0098 (9)0.0050 (9)
O20.0640 (10)0.0726 (12)0.0539 (10)0.0033 (8)0.0089 (8)0.0253 (8)
N10.0441 (9)0.0359 (8)0.0268 (8)0.0041 (7)0.0012 (6)0.0023 (7)
N20.0272 (8)0.0362 (8)0.0301 (8)0.0006 (7)0.0020 (6)0.0032 (7)
N30.0359 (9)0.0719 (13)0.0349 (9)0.0018 (9)0.0004 (7)0.0080 (9)
C10.0234 (8)0.0406 (10)0.0298 (9)0.0020 (7)0.0030 (7)0.0014 (8)
C20.0518 (12)0.0397 (11)0.0341 (10)0.0012 (9)0.0002 (8)0.0025 (9)
C30.0508 (12)0.0527 (13)0.0306 (10)0.0033 (10)0.0012 (8)0.0079 (9)
C40.0277 (9)0.0528 (12)0.0289 (9)0.0020 (8)0.0003 (7)0.0037 (9)
C50.0269 (9)0.0433 (11)0.0429 (11)0.0001 (8)0.0005 (8)0.0064 (9)
C60.0317 (9)0.0404 (11)0.0344 (10)0.0005 (8)0.0001 (7)0.0038 (8)
C70.0342 (9)0.0388 (10)0.0291 (9)0.0075 (8)0.0028 (7)0.0002 (8)
C80.0358 (9)0.0312 (9)0.0288 (9)0.0000 (8)0.0048 (7)0.0006 (7)
C90.0438 (11)0.0314 (10)0.0363 (10)0.0062 (8)0.0056 (8)0.0005 (8)
C100.0523 (11)0.0346 (10)0.0335 (10)0.0058 (9)0.0005 (8)0.0011 (8)
C110.0313 (10)0.0398 (11)0.0446 (11)0.0015 (8)0.0029 (8)0.0100 (9)
C12A0.0369 (14)0.068 (2)0.067 (3)0.0037 (13)0.0025 (19)0.036 (2)
C12B0.0369 (14)0.068 (2)0.067 (3)0.0037 (13)0.0025 (19)0.036 (2)
O30.0386 (8)0.0484 (8)0.0695 (10)0.0011 (7)0.0020 (7)0.0248 (8)
O40.0308 (8)0.0745 (11)0.0724 (11)0.0014 (7)0.0055 (7)0.0315 (8)
F1A0.0316 (11)0.103 (2)0.128 (3)0.0196 (12)0.0112 (14)0.0703 (18)
F2A0.0739 (15)0.0495 (14)0.168 (4)0.0015 (12)0.012 (2)0.0513 (17)
F3A0.146 (3)0.168 (3)0.0625 (16)0.035 (2)0.0317 (15)0.0260 (18)
F1B0.055 (4)0.112 (6)0.100 (5)0.010 (5)0.006 (4)0.068 (4)
F2B0.036 (4)0.120 (5)0.111 (5)0.015 (4)0.032 (4)0.057 (4)
F3B0.126 (5)0.083 (5)0.178 (6)0.035 (4)0.003 (5)0.029 (5)
Geometric parameters (Å, º) top
O1—N31.219 (2)C7—C81.505 (2)
O2—N31.220 (2)C7—H7A0.9700
N1—C11.368 (2)C7—H7B0.9700
N1—C101.452 (2)C8—H8A0.9700
N1—C71.452 (2)C8—H8B0.9700
N2—C91.485 (2)C9—C101.512 (3)
N2—C81.486 (2)C9—H9A0.9700
N2—H210.901 (15)C9—H9B0.9700
N2—H220.873 (15)C10—H10A0.9700
N3—C41.439 (2)C10—H10B0.9700
C1—C61.399 (3)C11—O31.224 (2)
C1—C21.408 (2)C11—O41.235 (2)
C2—C31.365 (3)C11—C12B1.518 (15)
C2—H20.9300C11—C12A1.539 (4)
C3—C41.375 (3)C12A—F2A1.306 (5)
C3—H30.9300C12A—F3A1.307 (5)
C4—C51.377 (3)C12A—F1A1.364 (5)
C5—C61.370 (3)C12B—F3B1.319 (13)
C5—H50.9300C12B—F1B1.332 (14)
C6—H60.9300C12B—F2B1.365 (14)
C1—N1—C10123.95 (15)N2—C8—C7109.25 (14)
C1—N1—C7123.34 (15)N2—C8—H8A109.8
C10—N1—C7110.45 (13)C7—C8—H8A109.8
C9—N2—C8111.88 (13)N2—C8—H8B109.8
C9—N2—H21107.2 (13)C7—C8—H8B109.8
C8—N2—H21110.4 (13)H8A—C8—H8B108.3
C9—N2—H22111.7 (13)N2—C9—C10109.95 (15)
C8—N2—H22107.8 (12)N2—C9—H9A109.7
H21—N2—H22107.9 (18)C10—C9—H9A109.7
O1—N3—O2122.05 (18)N2—C9—H9B109.7
O1—N3—C4118.42 (19)C10—C9—H9B109.7
O2—N3—C4119.53 (19)H9A—C9—H9B108.2
N1—C1—C6121.82 (16)N1—C10—C9110.05 (15)
N1—C1—C2120.84 (17)N1—C10—H10A109.7
C6—C1—C2117.31 (16)C9—C10—H10A109.7
C3—C2—C1120.96 (18)N1—C10—H10B109.7
C3—C2—H2119.5C9—C10—H10B109.7
C1—C2—H2119.5H10A—C10—H10B108.2
C2—C3—C4120.06 (18)O3—C11—O4130.58 (17)
C2—C3—H3120.0O3—C11—C12B111.0 (6)
C4—C3—H3120.0O4—C11—C12B116.9 (6)
C3—C4—C5120.72 (17)O3—C11—C12A115.9 (2)
C3—C4—N3119.83 (18)O4—C11—C12A113.3 (2)
C5—C4—N3119.45 (18)F2A—C12A—F3A104.5 (4)
C6—C5—C4119.45 (18)F2A—C12A—F1A103.1 (4)
C6—C5—H5120.3F3A—C12A—F1A112.0 (4)
C4—C5—H5120.3F2A—C12A—C11113.1 (3)
C5—C6—C1121.49 (17)F3A—C12A—C11112.2 (3)
C5—C6—H6119.3F1A—C12A—C11111.5 (3)
C1—C6—H6119.3F3B—C12B—F1B105.1 (13)
N1—C7—C8110.83 (14)F3B—C12B—F2B129.5 (15)
N1—C7—H7A109.5F1B—C12B—F2B89.6 (11)
C8—C7—H7A109.5F3B—C12B—C11112.5 (10)
N1—C7—H7B109.5F1B—C12B—C11108.2 (11)
C8—C7—H7B109.5F2B—C12B—C11107.8 (11)
H7A—C7—H7B108.1
C10—N1—C1—C6157.34 (17)C10—N1—C7—C861.08 (19)
C7—N1—C1—C63.9 (3)C9—N2—C8—C754.85 (18)
C10—N1—C1—C224.9 (2)N1—C7—C8—N257.36 (18)
C7—N1—C1—C2173.79 (16)C8—N2—C9—C1054.97 (19)
N1—C1—C2—C3178.48 (17)C1—N1—C10—C9103.02 (19)
C6—C1—C2—C30.7 (3)C7—N1—C10—C960.34 (19)
C1—C2—C3—C40.2 (3)N2—C9—C10—N156.90 (19)
C2—C3—C4—C50.7 (3)O3—C11—C12A—F2A139.1 (3)
C2—C3—C4—N3179.71 (17)O4—C11—C12A—F2A45.3 (4)
O1—N3—C4—C34.9 (3)O3—C11—C12A—F3A103.0 (3)
O2—N3—C4—C3175.97 (18)O4—C11—C12A—F3A72.6 (4)
O1—N3—C4—C5175.49 (18)O3—C11—C12A—F1A23.5 (5)
O2—N3—C4—C53.6 (3)O4—C11—C12A—F1A160.9 (3)
C3—C4—C5—C61.1 (3)O3—C11—C12B—F3B98.1 (11)
N3—C4—C5—C6179.33 (15)O4—C11—C12B—F3B69.4 (12)
C4—C5—C6—C10.6 (3)O3—C11—C12B—F1B146.3 (10)
N1—C1—C6—C5178.08 (16)O4—C11—C12B—F1B46.2 (12)
C2—C1—C6—C50.3 (3)O3—C11—C12B—F2B50.7 (12)
C1—N1—C7—C8102.40 (18)O4—C11—C12B—F2B141.8 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O30.90 (2)1.98 (2)2.844 (2)161 (2)
N2—H22···O4i0.87 (2)1.93 (2)2.786 (2)165 (2)
C7—H7A···O3i0.972.533.492 (2)169
Symmetry code: (i) x+1, y, z.
4-(4-Nitrophenyl)piperazin-1-ium trichloroacetate (II) top
Crystal data top
C10H14N3O2+·C2Cl3O2F(000) = 760
Mr = 370.61Dx = 1.603 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.7825 (5) ÅCell parameters from 2813 reflections
b = 6.6142 (3) Åθ = 3.0–27.8°
c = 20.3271 (9) ŵ = 0.62 mm1
β = 104.173 (4)°T = 293 K
V = 1535.91 (12) Å3Prism, brown
Z = 40.48 × 0.44 × 0.40 mm
Data collection top
Oxford Diffraction Xcalibu with Sapphire CCD
diffractometer
2068 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.013
Rotation method data acquisition using ω scans.θmax = 25.4°, θmin = 3.0°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction (2009)
h = 1413
Tmin = 0.840, Tmax = 1.000k = 76
5078 measured reflectionsl = 2414
2802 independent reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.0553P)2 + 0.1937P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.104(Δ/σ)max < 0.001
S = 1.09Δρmax = 0.25 e Å3
2802 reflectionsΔρmin = 0.28 e Å3
236 parametersExtinction correction: SHELXL2019/2 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
35 restraintsExtinction coefficient: 0.0084 (12)
Primary atom site location: structure-invariant direct methods
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)
O11.25261 (14)0.5140 (3)0.20561 (10)0.0741 (5)
O21.24364 (14)0.5039 (2)0.30936 (10)0.0669 (5)
N10.70718 (14)0.5089 (3)0.16441 (8)0.0449 (4)
N20.47368 (15)0.3654 (3)0.13414 (9)0.0428 (4)
N31.19635 (15)0.5092 (2)0.24883 (10)0.0477 (5)
C10.82694 (16)0.5103 (2)0.18508 (9)0.0332 (4)
C20.89695 (17)0.5088 (3)0.13812 (10)0.0410 (5)
H20.8613450.5085800.0919220.049*
C31.01632 (18)0.5077 (3)0.15913 (11)0.0432 (5)
H31.0611590.5065640.1273130.052*
C41.07033 (16)0.5084 (3)0.22736 (10)0.0369 (4)
C51.00483 (17)0.5083 (3)0.27476 (10)0.0379 (5)
H51.0417170.5077040.3207780.046*
C60.88472 (17)0.5091 (3)0.25404 (9)0.0370 (4)
H60.8409850.5088720.2864200.044*
C70.63004 (17)0.5611 (3)0.20782 (11)0.0452 (5)
H7A0.5908600.6880090.1928890.054*
H7B0.6757410.5782460.2541380.054*
C80.54056 (16)0.3977 (3)0.20527 (10)0.0425 (5)
H8A0.5792930.2731100.2234400.051*
H8B0.4875200.4361250.2328400.051*
C90.55236 (18)0.3230 (3)0.08906 (10)0.0466 (5)
H9A0.5065150.3127580.0425280.056*
H9B0.5914560.1945560.1015610.056*
C100.64214 (18)0.4869 (3)0.09421 (10)0.0489 (5)
H10A0.6953240.4531100.0662210.059*
H10B0.6037910.6134580.0779350.059*
O30.39831 (14)0.0360 (2)0.13071 (8)0.0613 (5)
O40.35547 (15)0.3109 (2)0.06595 (8)0.0619 (5)
C110.33900 (17)0.1382 (3)0.08446 (10)0.0412 (5)
C120.22438 (17)0.0367 (3)0.04153 (9)0.0394 (5)
Cl1A0.1882 (4)0.1717 (9)0.0837 (2)0.0708 (9)0.494 (15)
Cl2A0.2502 (7)0.0289 (11)0.0355 (3)0.0911 (17)0.494 (15)
Cl3A0.1076 (4)0.2089 (7)0.0240 (3)0.0746 (11)0.494 (15)
Cl1B0.2023 (4)0.2189 (9)0.0640 (4)0.0790 (16)0.506 (15)
Cl2B0.2284 (6)0.0136 (10)0.0438 (2)0.0839 (13)0.506 (15)
Cl3B0.1049 (4)0.1756 (13)0.0517 (5)0.100 (2)0.506 (15)
H210.4277 (18)0.263 (3)0.1340 (11)0.047 (6)*
H220.4300 (19)0.468 (3)0.1176 (11)0.061 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0405 (9)0.0979 (15)0.0875 (13)0.0003 (9)0.0227 (9)0.0052 (10)
O20.0443 (9)0.0759 (12)0.0697 (11)0.0015 (8)0.0068 (8)0.0106 (9)
N10.0330 (9)0.0664 (12)0.0364 (9)0.0058 (8)0.0106 (7)0.0123 (8)
N20.0334 (9)0.0375 (10)0.0536 (11)0.0019 (8)0.0033 (8)0.0032 (8)
N30.0357 (9)0.0363 (10)0.0689 (13)0.0012 (7)0.0087 (9)0.0069 (8)
C10.0344 (10)0.0273 (9)0.0388 (10)0.0020 (8)0.0106 (8)0.0025 (8)
C20.0406 (11)0.0483 (12)0.0350 (10)0.0030 (9)0.0108 (8)0.0016 (9)
C30.0405 (11)0.0439 (12)0.0491 (12)0.0042 (9)0.0181 (9)0.0022 (9)
C40.0333 (10)0.0252 (9)0.0506 (12)0.0004 (8)0.0076 (8)0.0017 (8)
C50.0429 (11)0.0286 (10)0.0395 (10)0.0014 (8)0.0046 (9)0.0032 (8)
C60.0423 (11)0.0349 (10)0.0359 (10)0.0026 (8)0.0136 (8)0.0024 (8)
C70.0348 (10)0.0567 (12)0.0464 (12)0.0050 (9)0.0144 (9)0.0130 (10)
C80.0368 (10)0.0466 (12)0.0442 (11)0.0020 (9)0.0104 (8)0.0017 (9)
C90.0449 (12)0.0509 (12)0.0388 (11)0.0026 (10)0.0001 (9)0.0060 (9)
C100.0391 (11)0.0675 (15)0.0386 (11)0.0004 (10)0.0066 (8)0.0006 (10)
O30.0579 (10)0.0507 (9)0.0598 (10)0.0039 (8)0.0152 (8)0.0023 (7)
O40.0640 (10)0.0505 (9)0.0616 (10)0.0210 (8)0.0030 (8)0.0044 (8)
C110.0383 (11)0.0456 (12)0.0375 (11)0.0031 (9)0.0054 (8)0.0057 (9)
C120.0386 (11)0.0401 (10)0.0378 (11)0.0010 (9)0.0062 (8)0.0024 (8)
Cl1A0.0801 (15)0.0735 (19)0.0577 (13)0.0376 (13)0.0150 (12)0.0120 (11)
Cl2A0.121 (3)0.099 (3)0.067 (3)0.040 (2)0.050 (2)0.053 (2)
Cl3A0.0501 (11)0.0651 (12)0.095 (2)0.0146 (8)0.0082 (13)0.0026 (15)
Cl1B0.0603 (14)0.0597 (17)0.095 (3)0.0272 (12)0.0224 (15)0.0358 (18)
Cl2B0.100 (2)0.107 (3)0.0388 (11)0.060 (2)0.0071 (13)0.0062 (15)
Cl3B0.0427 (9)0.115 (3)0.137 (4)0.0141 (15)0.0102 (19)0.063 (3)
Geometric parameters (Å, º) top
O1—N31.224 (3)C7—C81.502 (3)
O2—N31.221 (2)C7—H7A0.9700
N1—C11.370 (2)C7—H7B0.9700
N1—C101.452 (2)C8—H8A0.9700
N1—C71.455 (2)C8—H8B0.9700
N2—C91.481 (3)C9—C101.501 (3)
N2—C81.483 (2)C9—H9A0.9700
N2—H210.867 (16)C9—H9B0.9700
N2—H220.870 (16)C10—H10A0.9700
N3—C41.442 (2)C10—H10B0.9700
C1—C61.400 (3)O3—C111.228 (2)
C1—C21.406 (3)O4—C111.233 (2)
C2—C31.366 (3)C11—C121.568 (3)
C2—H20.9300C12—Cl2A1.722 (4)
C3—C41.377 (3)C12—Cl1A1.730 (5)
C3—H30.9300C12—Cl3B1.736 (4)
C4—C51.374 (3)C12—Cl2B1.753 (5)
C5—C61.374 (3)C12—Cl3A1.754 (5)
C5—H50.9300C12—Cl1B1.787 (4)
C6—H60.9300
C1—N1—C10123.91 (16)H7A—C7—H7B108.1
C1—N1—C7124.18 (17)N2—C8—C7109.76 (16)
C10—N1—C7111.23 (17)N2—C8—H8A109.7
C9—N2—C8111.52 (15)C7—C8—H8A109.7
C9—N2—H21109.6 (14)N2—C8—H8B109.7
C8—N2—H21107.4 (14)C7—C8—H8B109.7
C9—N2—H22108.0 (16)H8A—C8—H8B108.2
C8—N2—H22112.8 (16)N2—C9—C10110.93 (16)
H21—N2—H22107 (2)N2—C9—H9A109.5
O2—N3—O1122.05 (19)C10—C9—H9A109.5
O2—N3—C4119.16 (19)N2—C9—H9B109.5
O1—N3—C4118.79 (19)C10—C9—H9B109.5
N1—C1—C6121.24 (17)H9A—C9—H9B108.0
N1—C1—C2121.54 (17)N1—C10—C9109.53 (17)
C6—C1—C2117.21 (18)N1—C10—H10A109.8
C3—C2—C1121.20 (18)C9—C10—H10A109.8
C3—C2—H2119.4N1—C10—H10B109.8
C1—C2—H2119.4C9—C10—H10B109.8
C2—C3—C4120.09 (19)H10A—C10—H10B108.2
C2—C3—H3120.0O3—C11—O4129.89 (19)
C4—C3—H3120.0O3—C11—C12116.20 (18)
C5—C4—C3120.39 (18)O4—C11—C12113.91 (17)
C5—C4—N3120.10 (18)C11—C12—Cl2A107.1 (3)
C3—C4—N3119.52 (18)C11—C12—Cl1A110.38 (19)
C4—C5—C6119.88 (18)Cl2A—C12—Cl1A111.7 (2)
C4—C5—H5120.1C11—C12—Cl3B108.7 (2)
C6—C5—H5120.1C11—C12—Cl2B111.1 (2)
C5—C6—C1121.24 (18)Cl3B—C12—Cl2B112.5 (3)
C5—C6—H6119.4C11—C12—Cl3A111.2 (2)
C1—C6—H6119.4Cl2A—C12—Cl3A106.4 (3)
N1—C7—C8110.22 (17)Cl1A—C12—Cl3A110.0 (2)
N1—C7—H7A109.6C11—C12—Cl1B114.97 (18)
C8—C7—H7A109.6Cl3B—C12—Cl1B107.3 (2)
N1—C7—H7B109.6Cl2B—C12—Cl1B102.2 (3)
C8—C7—H7B109.6
C10—N1—C1—C6172.70 (18)C10—N1—C7—C860.7 (2)
C7—N1—C1—C617.6 (3)C9—N2—C8—C754.7 (2)
C10—N1—C1—C26.0 (3)N1—C7—C8—N257.0 (2)
C7—N1—C1—C2163.77 (18)C8—N2—C9—C1054.9 (2)
N1—C1—C2—C3179.19 (18)C1—N1—C10—C9129.3 (2)
C6—C1—C2—C30.5 (3)C7—N1—C10—C959.8 (2)
C1—C2—C3—C40.1 (3)N2—C9—C10—N156.4 (2)
C2—C3—C4—C50.6 (3)O3—C11—C12—Cl2A105.8 (4)
C2—C3—C4—N3179.41 (18)O4—C11—C12—Cl2A74.1 (4)
O2—N3—C4—C52.1 (3)O3—C11—C12—Cl1A16.0 (3)
O1—N3—C4—C5178.32 (17)O4—C11—C12—Cl1A164.1 (3)
O2—N3—C4—C3177.92 (18)O3—C11—C12—Cl3B117.0 (5)
O1—N3—C4—C31.7 (3)O4—C11—C12—Cl3B63.2 (5)
C3—C4—C5—C60.5 (3)O3—C11—C12—Cl2B118.7 (3)
N3—C4—C5—C6179.50 (16)O4—C11—C12—Cl2B61.1 (3)
C4—C5—C6—C10.1 (3)O3—C11—C12—Cl3A138.3 (3)
N1—C1—C6—C5179.29 (17)O4—C11—C12—Cl3A41.8 (3)
C2—C1—C6—C50.6 (3)O3—C11—C12—Cl1B3.3 (5)
C1—N1—C7—C8128.4 (2)O4—C11—C12—Cl1B176.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O30.87 (2)2.01 (2)2.795 (2)151 (2)
N2—H21···Cl1A0.87 (2)2.82 (2)3.510 (5)138 (2)
N2—H22···O4i0.87 (2)1.89 (2)2.738 (2)167 (2)
Symmetry code: (i) x, y+1, z.
 

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