Download citation
Download citation
link to html
2,3,8,9,14,15-Hexamethyl- and 2,3,8,9,14,15-hexa­phenyl-5,6,11,12,17,18-hexa­zatri­naphthyl­ene (HATNMe6 and HATNPh6) are derivatives of hexa­aza­tri­naphthyl­ene (HATN). In the crystal structures of the two compounds, pronounced π–π stacking dominates the packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989018000725/wm5431sup1.cif
Contains datablocks 1, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018000725/wm54311sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018000725/wm54312sup3.hkl
Contains datablock 2

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018000725/wm54311sup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018000725/wm54312sup5.cml
Supplementary material

CCDC references: 1816408; 1816407

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.002 Å
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.080
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.746 PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.096 Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 2 Report
Alert level G PLAT333_ALERT_2_G Large Aver C6-Ring C-C Dist. C1 -C1_a 1.45 Ang. PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 12 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 2 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 1 Note PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by . 1 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 6 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 7 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Datablock: 2
Alert level G PLAT333_ALERT_2_G Large Aver C6-Ring C-C Dist. C1 -C6 1.45 Ang. PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 20 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 0 ALERT level C = Check. Ensure it is not caused by an omission or oversight 3 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: IPDS (Stoe, 1999) for (1); APEX2 (Bruker, 2013) for (2). Cell refinement: IPDS (Stoe, 1999) for (1); SAINT (Bruker, 2013) for (2). Data reduction: X-RED (Stoe, 2002) for (1); SAINT (Bruker, 2013) for (2). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (1); SHELXS2013/1 (Sheldrick, 2015a) for (2). For both structures, program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

2,3,8,9,14,15-Hexamethyl-5,6,11,12,17,18-hexaazatrinaphthylene (1) top
Crystal data top
C30H24N6Dx = 1.320 Mg m3
Mr = 468.55Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcnCell parameters from 5493 reflections
a = 11.6178 (8) Åθ = 2.3–26.2°
b = 15.7762 (8) ŵ = 0.08 mm1
c = 12.8621 (7) ÅT = 153 K
V = 2357.4 (2) Å3Prism, yellow
Z = 40.50 × 0.38 × 0.25 mm
F(000) = 984
Data collection top
Stoe IPDS
diffractometer
Rint = 0.057
Radiation source: sealed tubeθmax = 26.2°, θmin = 2.6°
φ scansh = 1414
23121 measured reflectionsk = 1919
2361 independent reflectionsl = 1516
1286 reflections with I > 2σ(I)
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.080 w = 1/[σ2(Fo2) + (0.050P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.75(Δ/σ)max < 0.001
2361 reflectionsΔρmax = 0.16 e Å3
166 parametersΔρmin = 0.14 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*/Ueq
N10.56074 (10)0.64519 (8)0.34566 (8)0.0255 (3)
N20.62730 (10)0.49478 (7)0.43437 (8)0.0265 (3)
N30.56076 (10)0.34059 (8)0.33894 (7)0.0252 (3)
C10.53175 (13)0.57382 (8)0.29813 (10)0.0226 (3)
C20.56581 (11)0.49314 (9)0.34649 (9)0.0225 (3)
C30.53343 (12)0.41546 (9)0.29893 (9)0.0225 (3)
C40.52959 (12)0.71863 (9)0.29846 (10)0.0247 (3)
C50.55513 (12)0.79701 (10)0.34611 (10)0.0283 (3)
H50.5926910.7973430.4117150.034*
C60.52734 (13)0.87212 (9)0.30047 (11)0.0314 (4)
C70.55470 (17)0.95456 (11)0.35433 (13)0.0502 (5)
H7A0.5792760.9430760.4258450.075*
H7B0.4859520.9905400.3552340.075*
H7C0.6166730.9836450.3169240.075*
C80.65625 (12)0.41882 (9)0.47584 (10)0.0246 (3)
C90.72310 (13)0.41486 (9)0.56818 (10)0.0288 (4)
H90.7450940.4660610.6016000.035*
C100.75658 (12)0.33909 (9)0.61015 (10)0.0281 (3)
C110.72339 (12)0.26111 (9)0.56134 (10)0.0266 (3)
C120.65713 (13)0.26394 (9)0.47327 (10)0.0269 (3)
H120.6334970.2123310.4417610.032*
C130.62308 (11)0.34154 (9)0.42814 (9)0.0238 (3)
C140.82859 (14)0.33631 (11)0.70797 (11)0.0398 (4)
H14A0.8469970.3942340.7298950.060*
H14B0.9000370.3052440.6942360.060*
H14C0.7854190.3076480.7631840.060*
C150.76172 (14)0.17752 (9)0.60460 (11)0.0367 (4)
H15A0.7290410.1314820.5628310.055*
H15B0.7352620.1721940.6766540.055*
H15C0.8459310.1742420.6026130.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0268 (6)0.0259 (7)0.0237 (5)0.0006 (6)0.0010 (5)0.0007 (5)
N20.0279 (6)0.0280 (7)0.0235 (6)0.0014 (6)0.0026 (5)0.0015 (5)
N30.0279 (6)0.0277 (7)0.0201 (5)0.0003 (6)0.0001 (5)0.0010 (5)
C10.0211 (7)0.0255 (9)0.0213 (6)0.0007 (6)0.0018 (6)0.0005 (5)
C20.0209 (7)0.0265 (8)0.0201 (6)0.0010 (7)0.0028 (6)0.0001 (6)
C30.0224 (7)0.0259 (8)0.0191 (6)0.0008 (6)0.0034 (6)0.0006 (5)
C40.0225 (7)0.0271 (9)0.0244 (7)0.0003 (7)0.0010 (6)0.0011 (6)
C50.0274 (8)0.0313 (9)0.0262 (7)0.0004 (7)0.0058 (6)0.0017 (6)
C60.0311 (8)0.0272 (9)0.0360 (8)0.0017 (7)0.0061 (6)0.0015 (6)
C70.0685 (13)0.0294 (10)0.0526 (9)0.0004 (9)0.0288 (9)0.0037 (8)
C80.0236 (8)0.0277 (9)0.0225 (7)0.0009 (6)0.0014 (6)0.0025 (6)
C90.0311 (9)0.0301 (9)0.0254 (7)0.0031 (7)0.0033 (6)0.0006 (6)
C100.0267 (8)0.0323 (9)0.0253 (6)0.0006 (7)0.0011 (6)0.0061 (6)
C110.0261 (8)0.0287 (9)0.0252 (7)0.0031 (6)0.0044 (6)0.0049 (6)
C120.0306 (8)0.0257 (8)0.0246 (7)0.0003 (6)0.0025 (6)0.0011 (5)
C130.0238 (7)0.0277 (8)0.0198 (6)0.0012 (7)0.0027 (5)0.0010 (6)
C140.0426 (9)0.0399 (10)0.0370 (8)0.0030 (8)0.0141 (7)0.0061 (7)
C150.0385 (10)0.0365 (10)0.0350 (8)0.0033 (8)0.0042 (7)0.0063 (6)
Geometric parameters (Å, º) top
N1—C11.3248 (17)C7—H7C0.9800
N1—C41.3571 (18)C8—C131.4181 (19)
N2—C21.3374 (15)C8—C91.4205 (19)
N2—C81.3541 (18)C9—C101.368 (2)
N3—C31.3270 (17)C9—H90.9500
N3—C131.3568 (16)C10—C111.434 (2)
C1—C1i1.441 (3)C10—C141.5115 (19)
C1—C21.4709 (19)C11—C121.3703 (19)
C2—C31.4203 (19)C11—C151.4990 (19)
C3—C3i1.479 (3)C12—C131.4115 (19)
C4—C51.412 (2)C12—H120.9500
C4—C4i1.424 (3)C14—H14A0.9800
C5—C61.361 (2)C14—H14B0.9800
C5—H50.9500C14—H14C0.9800
C6—C6i1.445 (3)C15—H15A0.9800
C6—C71.507 (2)C15—H15B0.9800
C7—H7A0.9800C15—H15C0.9800
C7—H7B0.9800
C1—N1—C4116.83 (11)C13—C8—C9118.20 (12)
C2—N2—C8116.65 (12)C10—C9—C8121.58 (14)
C3—N3—C13116.47 (12)C10—C9—H9119.2
N1—C1—C1i121.77 (8)C8—C9—H9119.2
N1—C1—C2118.16 (12)C9—C10—C11120.03 (12)
C1i—C1—C2120.07 (7)C9—C10—C14120.74 (14)
N2—C2—C3121.48 (13)C11—C10—C14119.24 (13)
N2—C2—C1118.97 (13)C12—C11—C10119.02 (13)
C3—C2—C1119.55 (11)C12—C11—C15120.17 (13)
N3—C3—C2122.52 (12)C10—C11—C15120.81 (12)
N3—C3—C3i117.11 (7)C11—C12—C13121.71 (13)
C2—C3—C3i120.37 (8)C11—C12—H12119.1
N1—C4—C5119.83 (12)C13—C12—H12119.1
N1—C4—C4i121.37 (7)N3—C13—C12119.18 (13)
C5—C4—C4i118.80 (8)N3—C13—C8121.36 (12)
C6—C5—C4121.70 (12)C12—C13—C8119.45 (11)
C6—C5—H5119.1C10—C14—H14A109.5
C4—C5—H5119.1C10—C14—H14B109.5
C5—C6—C6i119.44 (8)H14A—C14—H14B109.5
C5—C6—C7120.19 (13)C10—C14—H14C109.5
C6i—C6—C7120.36 (9)H14A—C14—H14C109.5
C6—C7—H7A109.5H14B—C14—H14C109.5
C6—C7—H7B109.5C11—C15—H15A109.5
H7A—C7—H7B109.5C11—C15—H15B109.5
C6—C7—H7C109.5H15A—C15—H15B109.5
H7A—C7—H7C109.5C11—C15—H15C109.5
H7B—C7—H7C109.5H15A—C15—H15C109.5
N2—C8—C13121.52 (12)H15B—C15—H15C109.5
N2—C8—C9120.27 (13)
C4—N1—C1—C1i1.1 (2)C2—N2—C8—C130.12 (18)
C4—N1—C1—C2179.08 (13)C2—N2—C8—C9178.97 (12)
C8—N2—C2—C30.44 (17)N2—C8—C9—C10178.02 (13)
C8—N2—C2—C1179.87 (12)C13—C8—C9—C100.9 (2)
N1—C1—C2—N21.96 (18)C8—C9—C10—C110.5 (2)
C1i—C1—C2—N2178.26 (15)C8—C9—C10—C14179.46 (14)
N1—C1—C2—C3178.35 (13)C9—C10—C11—C120.7 (2)
C1i—C1—C2—C31.4 (2)C14—C10—C11—C12179.35 (13)
C13—N3—C3—C20.70 (18)C9—C10—C11—C15178.43 (14)
C13—N3—C3—C3i179.36 (15)C14—C10—C11—C151.56 (19)
N2—C2—C3—N30.77 (19)C10—C11—C12—C131.5 (2)
C1—C2—C3—N3179.54 (13)C15—C11—C12—C13177.59 (13)
N2—C2—C3—C3i179.28 (15)C3—N3—C13—C12178.55 (12)
C1—C2—C3—C3i0.4 (2)C3—N3—C13—C80.36 (17)
C1—N1—C4—C5178.39 (14)C11—C12—C13—N3177.78 (13)
C1—N1—C4—C4i1.1 (2)C11—C12—C13—C81.2 (2)
N1—C4—C5—C6178.74 (15)N2—C8—C13—N30.1 (2)
C4i—C4—C5—C61.7 (2)C9—C8—C13—N3178.96 (13)
C4—C5—C6—C6i1.5 (3)N2—C8—C13—C12178.83 (14)
C4—C5—C6—C7179.25 (15)C9—C8—C13—C120.04 (18)
Symmetry code: (i) x+1, y, z+1/2.
2,3,8,9,14,15-Hexaphenyl-5,6,11,12,17,18-hexazatrinaphthylene dichloromethane disolvate (2) top
Crystal data top
C60H36N6·2CH2Cl2Z = 2
Mr = 1010.80F(000) = 1044
Triclinic, P1Dx = 1.364 Mg m3
a = 9.2629 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 16.3829 (6) ÅCell parameters from 9893 reflections
c = 18.4366 (6) Åθ = 2.3–30.0°
α = 64.2659 (13)°µ = 0.29 mm1
β = 78.2616 (15)°T = 100 K
γ = 88.3530 (17)°Block, yellow
V = 2461.98 (16) Å30.30 × 0.12 × 0.10 mm
Data collection top
Bruker APEX-II CCD
diffractometer
11804 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.043
φ and ω scansθmax = 30.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 1313
Tmin = 0.970, Tmax = 1.000k = 2323
87137 measured reflectionsl = 2525
14377 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: difference Fourier map
wR(F2) = 0.107H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.050P)2 + 1.2P]
where P = (Fo2 + 2Fc2)/3
14377 reflections(Δ/σ)max = 0.001
649 parametersΔρmax = 0.84 e Å3
0 restraintsΔρmin = 0.84 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*/Ueq
N10.11926 (11)0.44967 (7)0.60814 (6)0.01193 (18)
N20.18060 (11)0.60400 (7)0.45277 (6)0.01252 (19)
N30.41523 (11)0.61360 (7)0.33603 (6)0.01264 (19)
N40.59471 (11)0.46401 (7)0.36209 (6)0.01232 (19)
N50.53889 (11)0.31547 (7)0.51241 (6)0.01196 (18)
N60.27642 (11)0.29872 (7)0.62955 (6)0.01280 (19)
C10.22651 (12)0.45307 (8)0.54672 (7)0.0107 (2)
C20.25958 (12)0.53194 (8)0.46923 (7)0.0111 (2)
C30.38735 (12)0.53672 (8)0.40497 (7)0.0110 (2)
C40.47903 (12)0.46219 (8)0.41903 (7)0.0109 (2)
C50.44562 (13)0.38091 (8)0.49903 (7)0.0110 (2)
C60.31672 (12)0.37406 (8)0.55998 (7)0.0113 (2)
C70.04205 (13)0.52505 (8)0.59315 (7)0.0116 (2)
C80.06780 (13)0.53019 (8)0.65653 (7)0.0132 (2)
H80.0888840.4793640.7091040.016*
C90.14549 (13)0.60696 (8)0.64431 (7)0.0128 (2)
C100.12054 (13)0.68304 (8)0.56292 (7)0.0128 (2)
C110.01485 (13)0.67705 (8)0.50117 (7)0.0142 (2)
H110.0005540.7257390.4473690.017*
C120.07124 (13)0.60140 (8)0.51484 (7)0.0122 (2)
C130.24727 (13)0.60780 (8)0.71806 (7)0.0140 (2)
C140.34319 (14)0.53190 (9)0.77210 (8)0.0175 (2)
H140.3447090.4804830.7610370.021*
C150.43664 (15)0.53104 (10)0.84210 (8)0.0229 (3)
H150.5021560.4794260.8781820.028*
C160.43391 (16)0.60558 (11)0.85904 (9)0.0244 (3)
H160.4979060.6051960.9065360.029*
C170.33734 (16)0.68085 (10)0.80636 (9)0.0233 (3)
H170.3346990.7316290.8182610.028*
C180.24461 (15)0.68200 (9)0.73633 (8)0.0181 (2)
H180.1789300.7336550.7006110.022*
C190.20291 (13)0.76731 (8)0.53886 (7)0.0139 (2)
C200.35316 (14)0.76736 (9)0.57128 (8)0.0161 (2)
H200.4047300.7131780.6141740.019*
C210.42778 (14)0.84646 (9)0.54103 (8)0.0185 (2)
H210.5293030.8459220.5644150.022*
C220.35570 (15)0.92581 (9)0.47732 (8)0.0197 (3)
H220.4083160.9787490.4558460.024*
C230.20617 (15)0.92744 (9)0.44508 (8)0.0193 (2)
H230.1557380.9817900.4018450.023*
C240.13024 (14)0.84933 (9)0.47618 (8)0.0172 (2)
H240.0273810.8513950.4546970.021*
C250.53512 (13)0.61711 (8)0.27859 (7)0.0127 (2)
C260.57330 (13)0.69798 (8)0.20488 (7)0.0144 (2)
H260.5166970.7491100.1980400.017*
C270.69015 (13)0.70462 (8)0.14283 (7)0.0134 (2)
C280.77379 (13)0.62586 (8)0.15212 (7)0.0136 (2)
C290.74119 (13)0.54812 (8)0.22552 (7)0.0145 (2)
H290.7991470.4974940.2324950.017*
C300.62378 (13)0.54171 (8)0.29071 (7)0.0124 (2)
C310.72725 (13)0.79506 (8)0.07089 (7)0.0135 (2)
C320.61387 (14)0.84510 (9)0.03578 (8)0.0161 (2)
H320.5153740.8187810.0547910.019*
C330.64453 (15)0.93319 (9)0.02681 (8)0.0183 (2)
H330.5668240.9668070.0500290.022*
C340.78795 (15)0.97199 (9)0.05534 (8)0.0184 (2)
H340.8085941.0322440.0977790.022*
C350.90129 (15)0.92247 (9)0.02165 (8)0.0186 (2)
H350.9997850.9488520.0415680.022*
C360.87189 (14)0.83442 (9)0.04111 (8)0.0168 (2)
H360.9502470.8010270.0637480.020*
C370.88799 (14)0.62319 (8)0.08340 (7)0.0145 (2)
C380.86264 (15)0.65702 (9)0.00340 (8)0.0192 (2)
H380.7744430.6861530.0084360.023*
C390.96540 (16)0.64836 (10)0.05883 (8)0.0222 (3)
H390.9468880.6715170.1128370.027*
C401.09477 (16)0.60612 (9)0.04259 (9)0.0226 (3)
H401.1645110.6001560.0852740.027*
C411.12205 (15)0.57251 (9)0.03644 (9)0.0206 (3)
H411.2106380.5436700.0478430.025*
C421.01925 (14)0.58124 (9)0.09874 (8)0.0172 (2)
H421.0385960.5583140.1525560.021*
C430.50237 (13)0.23986 (8)0.58462 (7)0.0120 (2)
C440.59874 (13)0.16847 (8)0.60277 (7)0.0136 (2)
H440.6916800.1766930.5663820.016*
C450.56063 (13)0.08732 (8)0.67207 (7)0.0127 (2)
C460.41889 (13)0.07453 (8)0.72707 (7)0.0132 (2)
C470.32768 (13)0.14531 (8)0.71244 (7)0.0142 (2)
H470.2367930.1375460.7503180.017*
C480.36715 (13)0.22959 (8)0.64178 (7)0.0126 (2)
C490.67019 (13)0.01680 (8)0.68874 (7)0.0133 (2)
C500.74324 (14)0.00492 (9)0.62584 (8)0.0165 (2)
H500.7174860.0222630.5734470.020*
C510.85324 (15)0.06598 (9)0.63947 (8)0.0197 (3)
H510.9014090.0807900.5965000.024*
C520.89332 (15)0.10554 (9)0.71539 (8)0.0198 (3)
H520.9700250.1462960.7240940.024*
C530.82030 (15)0.08504 (9)0.77862 (8)0.0189 (2)
H530.8465030.1122950.8308960.023*
C540.70939 (14)0.02491 (9)0.76543 (8)0.0162 (2)
H540.6592860.0118600.8091410.019*
C550.36807 (13)0.01519 (8)0.79842 (7)0.0143 (2)
C560.36616 (16)0.09418 (9)0.78719 (8)0.0212 (3)
H560.3976450.0908070.7335420.025*
C570.31856 (18)0.17757 (9)0.85392 (9)0.0259 (3)
H570.3162300.2307430.8455380.031*
C580.27434 (16)0.18366 (9)0.93285 (9)0.0226 (3)
H580.2430540.2408930.9785010.027*
C590.27614 (15)0.10594 (9)0.94456 (8)0.0184 (2)
H590.2465410.1099430.9985150.022*
C600.32114 (14)0.02160 (8)0.87767 (8)0.0153 (2)
H600.3198010.0316420.8861430.018*
Cl10.11062 (5)0.83590 (3)0.26669 (2)0.03512 (10)
Cl20.17654 (4)0.72871 (3)0.17281 (2)0.02962 (9)
C610.10609 (16)0.72602 (9)0.27127 (8)0.0218 (3)
H61A0.0029800.6993040.2917840.026*
H61B0.1656170.6868430.3105970.026*
Cl30.70558 (5)0.30628 (3)0.27367 (2)0.03072 (9)
Cl40.84801 (4)0.18745 (2)0.40649 (2)0.02374 (8)
C620.78838 (16)0.29773 (9)0.35492 (9)0.0208 (3)
H62A0.7162640.3119950.3947310.025*
H62B0.8740640.3427470.3324680.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0112 (4)0.0113 (4)0.0130 (4)0.0012 (4)0.0023 (4)0.0051 (4)
N20.0130 (4)0.0120 (5)0.0124 (4)0.0027 (4)0.0030 (4)0.0051 (4)
N30.0135 (5)0.0116 (5)0.0116 (4)0.0015 (4)0.0019 (4)0.0044 (4)
N40.0124 (4)0.0119 (5)0.0112 (4)0.0011 (4)0.0016 (4)0.0041 (4)
N50.0127 (4)0.0112 (5)0.0111 (4)0.0017 (4)0.0029 (4)0.0040 (4)
N60.0127 (4)0.0119 (5)0.0120 (4)0.0020 (4)0.0020 (4)0.0040 (4)
C10.0102 (5)0.0105 (5)0.0117 (5)0.0010 (4)0.0033 (4)0.0046 (4)
C20.0110 (5)0.0108 (5)0.0114 (5)0.0011 (4)0.0026 (4)0.0047 (4)
C30.0106 (5)0.0109 (5)0.0110 (5)0.0006 (4)0.0022 (4)0.0043 (4)
C40.0110 (5)0.0107 (5)0.0108 (5)0.0008 (4)0.0025 (4)0.0043 (4)
C50.0112 (5)0.0112 (5)0.0102 (5)0.0005 (4)0.0021 (4)0.0044 (4)
C60.0112 (5)0.0110 (5)0.0115 (5)0.0013 (4)0.0031 (4)0.0046 (4)
C70.0113 (5)0.0113 (5)0.0122 (5)0.0009 (4)0.0024 (4)0.0051 (4)
C80.0128 (5)0.0128 (5)0.0127 (5)0.0003 (4)0.0015 (4)0.0048 (4)
C90.0111 (5)0.0142 (5)0.0135 (5)0.0004 (4)0.0018 (4)0.0070 (4)
C100.0122 (5)0.0120 (5)0.0150 (5)0.0021 (4)0.0034 (4)0.0064 (4)
C110.0150 (5)0.0128 (5)0.0132 (5)0.0034 (4)0.0035 (4)0.0042 (4)
C120.0122 (5)0.0121 (5)0.0121 (5)0.0012 (4)0.0032 (4)0.0049 (4)
C130.0123 (5)0.0162 (6)0.0142 (5)0.0032 (4)0.0038 (4)0.0069 (5)
C140.0157 (6)0.0183 (6)0.0179 (6)0.0006 (5)0.0021 (5)0.0079 (5)
C150.0184 (6)0.0267 (7)0.0185 (6)0.0012 (5)0.0012 (5)0.0072 (5)
C160.0208 (6)0.0340 (8)0.0176 (6)0.0055 (6)0.0006 (5)0.0129 (6)
C170.0267 (7)0.0270 (7)0.0212 (6)0.0066 (6)0.0037 (5)0.0160 (6)
C180.0190 (6)0.0181 (6)0.0174 (6)0.0019 (5)0.0021 (5)0.0089 (5)
C190.0152 (5)0.0140 (5)0.0146 (5)0.0040 (4)0.0051 (4)0.0075 (5)
C200.0152 (5)0.0163 (6)0.0190 (6)0.0027 (4)0.0039 (5)0.0098 (5)
C210.0140 (5)0.0202 (6)0.0252 (6)0.0056 (5)0.0055 (5)0.0132 (5)
C220.0216 (6)0.0173 (6)0.0236 (6)0.0089 (5)0.0095 (5)0.0104 (5)
C230.0228 (6)0.0140 (6)0.0185 (6)0.0033 (5)0.0044 (5)0.0048 (5)
C240.0158 (6)0.0175 (6)0.0178 (6)0.0037 (5)0.0022 (5)0.0080 (5)
C250.0127 (5)0.0127 (5)0.0120 (5)0.0010 (4)0.0023 (4)0.0048 (4)
C260.0150 (5)0.0117 (5)0.0138 (5)0.0025 (4)0.0031 (4)0.0032 (4)
C270.0135 (5)0.0125 (5)0.0121 (5)0.0011 (4)0.0031 (4)0.0032 (4)
C280.0129 (5)0.0142 (5)0.0117 (5)0.0007 (4)0.0015 (4)0.0044 (4)
C290.0142 (5)0.0128 (5)0.0139 (5)0.0028 (4)0.0012 (4)0.0043 (4)
C300.0131 (5)0.0114 (5)0.0117 (5)0.0010 (4)0.0026 (4)0.0041 (4)
C310.0153 (5)0.0117 (5)0.0108 (5)0.0008 (4)0.0014 (4)0.0030 (4)
C320.0140 (5)0.0176 (6)0.0137 (5)0.0018 (4)0.0018 (4)0.0046 (5)
C330.0222 (6)0.0172 (6)0.0135 (5)0.0059 (5)0.0049 (5)0.0046 (5)
C340.0265 (7)0.0135 (6)0.0117 (5)0.0006 (5)0.0018 (5)0.0033 (5)
C350.0179 (6)0.0164 (6)0.0171 (6)0.0037 (5)0.0008 (5)0.0051 (5)
C360.0155 (6)0.0153 (6)0.0169 (6)0.0012 (4)0.0032 (5)0.0047 (5)
C370.0158 (5)0.0126 (5)0.0122 (5)0.0013 (4)0.0007 (4)0.0043 (4)
C380.0226 (6)0.0170 (6)0.0150 (6)0.0012 (5)0.0023 (5)0.0052 (5)
C390.0304 (7)0.0204 (6)0.0127 (6)0.0022 (5)0.0003 (5)0.0063 (5)
C400.0258 (7)0.0195 (6)0.0197 (6)0.0052 (5)0.0071 (5)0.0108 (5)
C410.0176 (6)0.0182 (6)0.0236 (6)0.0008 (5)0.0026 (5)0.0098 (5)
C420.0177 (6)0.0158 (6)0.0154 (6)0.0005 (5)0.0008 (5)0.0054 (5)
C430.0136 (5)0.0116 (5)0.0104 (5)0.0013 (4)0.0021 (4)0.0048 (4)
C440.0137 (5)0.0138 (5)0.0122 (5)0.0032 (4)0.0017 (4)0.0052 (4)
C450.0148 (5)0.0125 (5)0.0112 (5)0.0032 (4)0.0031 (4)0.0055 (4)
C460.0156 (5)0.0116 (5)0.0113 (5)0.0012 (4)0.0027 (4)0.0041 (4)
C470.0143 (5)0.0130 (5)0.0122 (5)0.0013 (4)0.0006 (4)0.0035 (4)
C480.0129 (5)0.0120 (5)0.0121 (5)0.0014 (4)0.0025 (4)0.0046 (4)
C490.0143 (5)0.0102 (5)0.0134 (5)0.0018 (4)0.0024 (4)0.0035 (4)
C500.0197 (6)0.0153 (6)0.0144 (5)0.0038 (5)0.0033 (5)0.0067 (5)
C510.0227 (6)0.0182 (6)0.0196 (6)0.0066 (5)0.0030 (5)0.0105 (5)
C520.0206 (6)0.0162 (6)0.0233 (6)0.0073 (5)0.0063 (5)0.0090 (5)
C530.0228 (6)0.0162 (6)0.0172 (6)0.0062 (5)0.0079 (5)0.0056 (5)
C540.0189 (6)0.0151 (6)0.0144 (5)0.0044 (5)0.0035 (5)0.0065 (5)
C550.0143 (5)0.0117 (5)0.0135 (5)0.0012 (4)0.0022 (4)0.0028 (4)
C560.0297 (7)0.0156 (6)0.0164 (6)0.0010 (5)0.0013 (5)0.0066 (5)
C570.0372 (8)0.0130 (6)0.0238 (7)0.0034 (6)0.0002 (6)0.0073 (5)
C580.0266 (7)0.0133 (6)0.0200 (6)0.0026 (5)0.0006 (5)0.0015 (5)
C590.0193 (6)0.0169 (6)0.0137 (5)0.0003 (5)0.0000 (5)0.0033 (5)
C600.0153 (5)0.0136 (5)0.0147 (5)0.0012 (4)0.0015 (4)0.0048 (5)
Cl10.0569 (3)0.01799 (17)0.02317 (17)0.00789 (16)0.00341 (17)0.00389 (14)
Cl20.03465 (19)0.0337 (2)0.01836 (16)0.00290 (15)0.00656 (14)0.00909 (14)
C610.0273 (7)0.0158 (6)0.0156 (6)0.0027 (5)0.0028 (5)0.0013 (5)
Cl30.0449 (2)0.02792 (18)0.01921 (16)0.00109 (16)0.01175 (15)0.00788 (14)
Cl40.02025 (15)0.02240 (16)0.02590 (16)0.00880 (12)0.00300 (12)0.00941 (13)
C620.0233 (6)0.0187 (6)0.0233 (6)0.0049 (5)0.0087 (5)0.0106 (5)
Geometric parameters (Å, º) top
N1—C11.3278 (15)C31—C321.4001 (17)
N1—C71.3588 (15)C32—C331.3925 (18)
N2—C21.3231 (15)C32—H320.9500
N2—C121.3513 (15)C33—C341.3854 (19)
N3—C31.3279 (15)C33—H330.9500
N3—C251.3529 (15)C34—C351.3875 (19)
N4—C41.3296 (15)C34—H340.9500
N4—C301.3585 (15)C35—C361.3923 (18)
N5—C51.3268 (15)C35—H350.9500
N5—C431.3528 (15)C36—H360.9500
N6—C61.3286 (15)C37—C421.3978 (18)
N6—C481.3567 (15)C37—C381.4004 (17)
C1—C21.4305 (16)C38—C391.3899 (18)
C1—C61.4763 (16)C38—H380.9500
C2—C31.4713 (16)C39—C401.387 (2)
C3—C41.4263 (16)C39—H390.9500
C4—C51.4755 (16)C40—C411.391 (2)
C5—C61.4328 (16)C40—H400.9500
C7—C81.4159 (16)C41—C421.3915 (18)
C7—C121.4192 (16)C41—H410.9500
C8—C91.3851 (16)C42—H420.9500
C8—H80.9500C43—C441.4136 (16)
C9—C101.4526 (17)C43—C481.4244 (16)
C9—C131.4939 (16)C44—C451.3759 (17)
C10—C111.3792 (16)C44—H440.9500
C10—C191.4934 (16)C45—C461.4440 (16)
C11—C121.4103 (16)C45—C491.4868 (16)
C11—H110.9500C46—C471.3770 (17)
C13—C181.3973 (17)C46—C551.4905 (16)
C13—C141.3984 (18)C47—C481.4179 (16)
C14—C151.3948 (18)C47—H470.9500
C14—H140.9500C49—C541.3977 (17)
C15—C161.388 (2)C49—C501.3979 (17)
C15—H150.9500C50—C511.3891 (18)
C16—C171.391 (2)C50—H500.9500
C16—H160.9500C51—C521.3880 (19)
C17—C181.3907 (18)C51—H510.9500
C17—H170.9500C52—C531.3911 (19)
C18—H180.9500C52—H520.9500
C19—C201.3987 (17)C53—C541.3858 (17)
C19—C241.4075 (18)C53—H530.9500
C20—C211.3949 (17)C54—H540.9500
C20—H200.9500C55—C601.3949 (17)
C21—C221.386 (2)C55—C561.3976 (18)
C21—H210.9500C56—C571.3889 (19)
C22—C231.3877 (19)C56—H560.9500
C22—H220.9500C57—C581.389 (2)
C23—C241.3915 (18)C57—H570.9500
C23—H230.9500C58—C591.3818 (19)
C24—H240.9500C58—H580.9500
C25—C261.4124 (16)C59—C601.3957 (17)
C25—C301.4237 (16)C59—H590.9500
C26—C271.3736 (17)C60—H600.9500
C26—H260.9500Cl1—C611.7665 (14)
C27—C281.4489 (17)Cl2—C611.7812 (14)
C27—C311.4865 (16)C61—H61A0.9900
C28—C291.3798 (17)C61—H61B0.9900
C28—C371.4920 (16)Cl3—C621.7695 (14)
C29—C301.4155 (16)Cl4—C621.7713 (14)
C29—H290.9500C62—H62A0.9900
C31—C361.3983 (17)C62—H62B0.9900
C1—N1—C7116.30 (10)C33—C32—C31120.44 (12)
C2—N2—C12116.39 (10)C33—C32—H32119.8
C3—N3—C25116.16 (10)C31—C32—H32119.8
C4—N4—C30116.49 (10)C34—C33—C32120.24 (12)
C5—N5—C43116.77 (10)C34—C33—H33119.9
C6—N6—C48116.57 (10)C32—C33—H33119.9
N1—C1—C2121.85 (10)C33—C34—C35119.71 (12)
N1—C1—C6118.82 (10)C33—C34—H34120.1
C2—C1—C6119.30 (10)C35—C34—H34120.1
N2—C2—C1122.22 (10)C34—C35—C36120.55 (12)
N2—C2—C3117.20 (10)C34—C35—H35119.7
C1—C2—C3120.56 (10)C36—C35—H35119.7
N3—C3—C4122.47 (10)C35—C36—C31120.13 (12)
N3—C3—C2117.23 (10)C35—C36—H36119.9
C4—C3—C2120.26 (10)C31—C36—H36119.9
N4—C4—C3121.81 (10)C42—C37—C38118.35 (11)
N4—C4—C5118.87 (10)C42—C37—C28120.41 (11)
C3—C4—C5119.32 (10)C38—C37—C28121.10 (11)
N5—C5—C6121.65 (10)C39—C38—C37120.58 (13)
N5—C5—C4117.87 (10)C39—C38—H38119.7
C6—C5—C4120.48 (10)C37—C38—H38119.7
N6—C6—C5121.95 (10)C40—C39—C38120.43 (13)
N6—C6—C1118.34 (10)C40—C39—H39119.8
C5—C6—C1119.70 (10)C38—C39—H39119.8
N1—C7—C8120.43 (11)C39—C40—C41119.76 (12)
N1—C7—C12121.41 (10)C39—C40—H40120.1
C8—C7—C12118.14 (10)C41—C40—H40120.1
C9—C8—C7122.09 (11)C40—C41—C42119.84 (13)
C9—C8—H8119.0C40—C41—H41120.1
C7—C8—H8119.0C42—C41—H41120.1
C8—C9—C10119.46 (10)C41—C42—C37121.05 (12)
C8—C9—C13117.04 (11)C41—C42—H42119.5
C10—C9—C13123.45 (10)C37—C42—H42119.5
C11—C10—C9118.05 (10)N5—C43—C44119.26 (10)
C11—C10—C19116.27 (11)N5—C43—C48121.46 (11)
C9—C10—C19125.65 (10)C44—C43—C48119.27 (11)
C10—C11—C12122.52 (11)C45—C44—C43121.32 (11)
C10—C11—H11118.7C45—C44—H44119.3
C12—C11—H11118.7C43—C44—H44119.3
N2—C12—C11118.80 (11)C44—C45—C46119.37 (11)
N2—C12—C7121.68 (11)C44—C45—C49118.20 (11)
C11—C12—C7119.51 (11)C46—C45—C49122.40 (10)
C18—C13—C14118.81 (11)C47—C46—C45119.76 (11)
C18—C13—C9121.17 (11)C47—C46—C55119.40 (11)
C14—C13—C9119.97 (11)C45—C46—C55120.83 (10)
C15—C14—C13120.58 (12)C46—C47—C48121.10 (11)
C15—C14—H14119.7C46—C47—H47119.4
C13—C14—H14119.7C48—C47—H47119.4
C16—C15—C14119.99 (13)N6—C48—C47119.90 (11)
C16—C15—H15120.0N6—C48—C43121.16 (11)
C14—C15—H15120.0C47—C48—C43118.94 (11)
C15—C16—C17119.89 (12)C54—C49—C50118.52 (11)
C15—C16—H16120.1C54—C49—C45121.15 (11)
C17—C16—H16120.1C50—C49—C45120.21 (11)
C16—C17—C18120.19 (13)C51—C50—C49120.42 (12)
C16—C17—H17119.9C51—C50—H50119.8
C18—C17—H17119.9C49—C50—H50119.8
C17—C18—C13120.53 (13)C52—C51—C50120.52 (12)
C17—C18—H18119.7C52—C51—H51119.7
C13—C18—H18119.7C50—C51—H51119.7
C20—C19—C24117.96 (11)C51—C52—C53119.49 (12)
C20—C19—C10122.87 (11)C51—C52—H52120.3
C24—C19—C10118.98 (11)C53—C52—H52120.3
C21—C20—C19120.42 (12)C54—C53—C52120.07 (12)
C21—C20—H20119.8C54—C53—H53120.0
C19—C20—H20119.8C52—C53—H53120.0
C22—C21—C20120.84 (12)C53—C54—C49120.96 (11)
C22—C21—H21119.6C53—C54—H54119.5
C20—C21—H21119.6C49—C54—H54119.5
C21—C22—C23119.57 (12)C60—C55—C56118.87 (11)
C21—C22—H22120.2C60—C55—C46120.40 (11)
C23—C22—H22120.2C56—C55—C46120.73 (11)
C22—C23—C24119.89 (12)C57—C56—C55120.45 (12)
C22—C23—H23120.1C57—C56—H56119.8
C24—C23—H23120.1C55—C56—H56119.8
C23—C24—C19121.27 (12)C56—C57—C58120.36 (13)
C23—C24—H24119.4C56—C57—H57119.8
C19—C24—H24119.4C58—C57—H57119.8
N3—C25—C26118.94 (11)C59—C58—C57119.58 (12)
N3—C25—C30121.74 (11)C59—C58—H58120.2
C26—C25—C30119.32 (11)C57—C58—H58120.2
C27—C26—C25121.72 (11)C58—C59—C60120.47 (12)
C27—C26—H26119.1C58—C59—H59119.8
C25—C26—H26119.1C60—C59—H59119.8
C26—C27—C28119.20 (11)C55—C60—C59120.26 (12)
C26—C27—C31117.00 (11)C55—C60—H60119.9
C28—C27—C31123.74 (11)C59—C60—H60119.9
C29—C28—C27119.15 (11)Cl1—C61—Cl2111.51 (7)
C29—C28—C37118.19 (11)Cl1—C61—H61A109.3
C27—C28—C37122.53 (11)Cl2—C61—H61A109.3
C28—C29—C30121.82 (11)Cl1—C61—H61B109.3
C28—C29—H29119.1Cl2—C61—H61B109.3
C30—C29—H29119.1H61A—C61—H61B108.0
N4—C30—C29120.21 (11)Cl3—C62—Cl4111.38 (7)
N4—C30—C25121.24 (10)Cl3—C62—H62A109.4
C29—C30—C25118.52 (11)Cl4—C62—H62A109.4
C36—C31—C32118.92 (11)Cl3—C62—H62B109.4
C36—C31—C27121.40 (11)Cl4—C62—H62B109.4
C32—C31—C27119.51 (11)H62A—C62—H62B108.0
C7—N1—C1—C20.39 (16)C25—C26—C27—C281.87 (18)
C7—N1—C1—C6178.51 (10)C25—C26—C27—C31175.41 (11)
C12—N2—C2—C13.53 (16)C26—C27—C28—C294.81 (18)
C12—N2—C2—C3174.71 (10)C31—C27—C28—C29172.28 (11)
N1—C1—C2—N23.64 (17)C26—C27—C28—C37171.17 (11)
C6—C1—C2—N2178.24 (10)C31—C27—C28—C3711.75 (18)
N1—C1—C2—C3174.54 (10)C27—C28—C29—C302.96 (18)
C6—C1—C2—C33.57 (16)C37—C28—C29—C30173.19 (11)
C25—N3—C3—C41.04 (16)C4—N4—C30—C29177.43 (11)
C25—N3—C3—C2178.61 (10)C4—N4—C30—C250.63 (16)
N2—C2—C3—N31.24 (16)C28—C29—C30—N4179.89 (11)
C1—C2—C3—N3177.04 (10)C28—C29—C30—C251.78 (18)
N2—C2—C3—C4178.87 (10)N3—C25—C30—N42.53 (18)
C1—C2—C3—C40.59 (16)C26—C25—C30—N4177.19 (11)
C30—N4—C4—C31.96 (16)N3—C25—C30—C29175.56 (11)
C30—N4—C4—C5177.66 (10)C26—C25—C30—C294.72 (17)
N3—C3—C4—N42.97 (18)C26—C27—C31—C36130.02 (13)
C2—C3—C4—N4179.52 (10)C28—C27—C31—C3647.12 (18)
N3—C3—C4—C5176.64 (10)C26—C27—C31—C3245.20 (16)
C2—C3—C4—C50.86 (16)C28—C27—C31—C32137.66 (13)
C43—N5—C5—C63.42 (16)C36—C31—C32—C331.07 (18)
C43—N5—C5—C4177.02 (10)C27—C31—C32—C33174.26 (11)
N4—C4—C5—N54.35 (16)C31—C32—C33—C340.42 (19)
C3—C4—C5—N5175.28 (10)C32—C33—C34—C350.43 (19)
N4—C4—C5—C6176.09 (10)C33—C34—C35—C360.6 (2)
C3—C4—C5—C64.28 (16)C34—C35—C36—C310.1 (2)
C48—N6—C6—C52.78 (16)C32—C31—C36—C350.90 (19)
C48—N6—C6—C1176.00 (10)C27—C31—C36—C35174.34 (12)
N5—C5—C6—N66.51 (18)C29—C28—C37—C4243.08 (17)
C4—C5—C6—N6173.94 (10)C27—C28—C37—C42140.91 (13)
N5—C5—C6—C1172.25 (10)C29—C28—C37—C38132.67 (13)
C4—C5—C6—C17.29 (16)C27—C28—C37—C3843.34 (18)
N1—C1—C6—N67.57 (16)C42—C37—C38—C390.43 (19)
C2—C1—C6—N6174.26 (10)C28—C37—C38—C39175.40 (12)
N1—C1—C6—C5171.24 (10)C37—C38—C39—C400.1 (2)
C2—C1—C6—C56.93 (16)C38—C39—C40—C410.2 (2)
C1—N1—C7—C8175.81 (10)C39—C40—C41—C420.2 (2)
C1—N1—C7—C122.53 (16)C40—C41—C42—C370.2 (2)
N1—C7—C8—C9177.93 (11)C38—C37—C42—C410.48 (19)
C12—C7—C8—C90.46 (17)C28—C37—C42—C41175.38 (12)
C7—C8—C9—C103.64 (18)C5—N5—C43—C44179.04 (11)
C7—C8—C9—C13173.85 (11)C5—N5—C43—C482.65 (16)
C8—C9—C10—C112.59 (17)N5—C43—C44—C45174.46 (11)
C13—C9—C10—C11174.73 (11)C48—C43—C44—C453.89 (18)
C8—C9—C10—C19175.49 (11)C43—C44—C45—C460.48 (18)
C13—C9—C10—C197.18 (18)C43—C44—C45—C49177.63 (11)
C9—C10—C11—C121.63 (18)C44—C45—C46—C474.07 (17)
C19—C10—C11—C12179.89 (11)C49—C45—C46—C47173.96 (11)
C2—N2—C12—C11178.93 (11)C44—C45—C46—C55174.32 (11)
C2—N2—C12—C70.57 (17)C49—C45—C46—C557.66 (17)
C10—C11—C12—N2174.68 (11)C45—C46—C47—C483.20 (18)
C10—C11—C12—C74.83 (18)C55—C46—C47—C48175.21 (11)
N1—C7—C12—N22.59 (18)C6—N6—C48—C47176.64 (11)
C8—C7—C12—N2175.78 (11)C6—N6—C48—C433.29 (17)
N1—C7—C12—C11177.91 (11)C46—C47—C48—N6178.90 (11)
C8—C7—C12—C113.71 (17)C46—C47—C48—C431.18 (18)
C8—C9—C13—C18131.14 (13)N5—C43—C48—N66.33 (18)
C10—C9—C13—C1846.24 (17)C44—C43—C48—N6175.36 (11)
C8—C9—C13—C1446.20 (16)N5—C43—C48—C47173.60 (11)
C10—C9—C13—C14136.41 (12)C44—C43—C48—C474.71 (17)
C18—C13—C14—C151.27 (19)C44—C45—C49—C54128.73 (13)
C9—C13—C14—C15178.68 (12)C46—C45—C49—C5449.32 (17)
C13—C14—C15—C160.6 (2)C44—C45—C49—C5047.16 (17)
C14—C15—C16—C170.3 (2)C46—C45—C49—C50134.79 (13)
C15—C16—C17—C180.7 (2)C54—C49—C50—C510.62 (19)
C16—C17—C18—C130.0 (2)C45—C49—C50—C51175.38 (12)
C14—C13—C18—C170.95 (19)C49—C50—C51—C520.7 (2)
C9—C13—C18—C17178.32 (12)C50—C51—C52—C531.3 (2)
C11—C10—C19—C20143.00 (12)C51—C52—C53—C540.6 (2)
C9—C10—C19—C2035.12 (18)C52—C53—C54—C490.8 (2)
C11—C10—C19—C2431.82 (16)C50—C49—C54—C531.35 (19)
C9—C10—C19—C24150.07 (12)C45—C49—C54—C53174.61 (12)
C24—C19—C20—C210.87 (18)C47—C46—C55—C6054.54 (16)
C10—C19—C20—C21174.00 (11)C45—C46—C55—C60127.07 (13)
C19—C20—C21—C221.38 (19)C47—C46—C55—C56125.28 (14)
C20—C21—C22—C232.2 (2)C45—C46—C55—C5653.11 (17)
C21—C22—C23—C240.8 (2)C60—C55—C56—C570.1 (2)
C22—C23—C24—C191.5 (2)C46—C55—C56—C57179.94 (13)
C20—C19—C24—C232.31 (19)C55—C56—C57—C581.0 (2)
C10—C19—C24—C23172.76 (11)C56—C57—C58—C590.8 (2)
C3—N3—C25—C26178.15 (11)C57—C58—C59—C600.4 (2)
C3—N3—C25—C301.57 (17)C56—C55—C60—C591.33 (19)
N3—C25—C26—C27177.36 (11)C46—C55—C60—C59178.84 (12)
C30—C25—C26—C272.91 (18)C58—C59—C60—C551.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C61—H61A···N1i0.992.463.2380 (17)135
C61—H61B···N20.992.403.2745 (17)146
C61—H61B···N30.992.613.4923 (18)149
C62—H62A···N40.992.583.2547 (17)126
C62—H62A···N50.992.463.4381 (17)169
Symmetry code: (i) x, y+1, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds