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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3110–o3111.
Published online 2010 November 10. doi:  10.1107/S1600536810045290
PMCID: PMC3011455

(Z)-3-Diethyl­amino-6-({2-[(E)-4-(diethyl­amino)-2-hy­droxy­benzyl­idene­amino]-4,5-dimethyl­phen­yl}amino­methyl­idene)cyclo­hexa-2,4-dienone–5,5′-bis­(diethyl­amino)-2,2′-[4,5-dimethyl-o-phenyl­enebis(nitrilo­methyl­idyne)]diphenol

Abstract

The asymmetric unit of the title Schiff base compound, C30H38N4O2, comprises two crystallographically independent mol­ecules, A and B. The structure is non-merohedrally twinned with a refined BASF ratio of 0.219 (6):0.701 (6). Mol­ecule B shows both phenol–imine and keto–amine tautomeric forms in a single structure. The dihedral angles between the central ring and the two outer rings are 5.9 (3) and 48.4 (3)° in mol­ecule A, and 48.3 (3) and 6.9 (3)° in mol­ecule B. Strong intra­molecular O—H(...)N and N—H(...)O hydrogen bonds generate S(6) ring motifs. The crystal structure is further stabilized by inter­molecular C—H(...)O, C—H(...)π and π–π inter­actions [centroid–centroid distances = 3.870 (4)–3.871 (4) Å].

Related literature

For standard values of bond lengths, see: Allen et al. (1987 [triangle]). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For related structures, see: Kargar et al. (2009 [triangle], 2010a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3110-scheme1.jpg

Experimental

Crystal data

  • C30H38N4O2
  • M r = 486.64
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3110-efi1.jpg
  • a = 11.4430 (12) Å
  • b = 12.0251 (12) Å
  • c = 22.171 (2) Å
  • α = 88.241 (6)°
  • β = 89.370 (7)°
  • γ = 65.207 (6)°
  • V = 2768.2 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 296 K
  • 0.24 × 0.19 × 0.11 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.983, T max = 0.992
  • 44348 measured reflections
  • 9655 independent reflections
  • 4485 reflections with I > 2σ(I)
  • R int = 0.095

Refinement

  • R[F 2 > 2σ(F 2)] = 0.106
  • wR(F 2) = 0.320
  • S = 1.06
  • 9655 reflections
  • 662 parameters
  • H-atom parameters constrained
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045290/hg2737sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045290/hg2737Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

HK thanks PNU for financial support. RK thanks the Science and Research Branch of the Islamic Azad University, Tehran. MNT thanks the University of Sargodha, Pakistan for the Research facility.

supplementary crystallographic information

Comment

Schiff base ligands are one of the most prevalent systems in coordination chemistry. As part of a general study of tetradenate Schiff bases (Kargar et al., 2009; Kargar et al., 2010a,b), we have determined the crystal structure of the title compound.

The asymmetric unit of the title Schiff base compound, Fig. 1, comprises two crystallographically independent molecules, A and B which is non-merohedrally twinned with a refined BASF ratio of 0.219 (6)/0.701 (6). Molecule B shows both phenol-imine and keto-amine tautomeric form in a single structure. The dihedral angles between the central phenyl ring with the two outer phenyl rings are 5.9 (3) and 48.4 (3)° in molecule A and 48.3 (3) and 6.9 (3)° in molecule B, respectively. Strong intramolecular O—H···N and N—H···O hydrogen bonds generate S(6) ring motifs. The crystal structure is further stabilized by the intermolecular C—H···π and π-π interactions [Cg1···Cg1i = 3.870 (4)Å, (i) -x, 1 - y, 1 - z; Cg2···Cg2ii = 3.871 (4)Å, (ii) 1 - x, 1 - y, -z; Cg1 and Cg2 are the centroids of C15–C20 and C33–C38 benzene rings].

Experimental

The title compound was synthesized by adding 4-N-diethylamino- salicylaldehyde (4 mmol) to a solution of 4,5-dimethyl-1,2-phenylenediamine (2 mmol) in ethanol (20 ml). The mixture was refluxed with stirring for half an hour. The resultant yellow solution was filtered. Yellow single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days. The quality of the crystal was not optimal and it was weakly diffracting. Although recrystallization was attempted repeatedly, we tried three data collections but no better data than this one was obtained.

Refinement

H atoms of the hydroxy and amino groups were located in a difference Fourier map. They first restrained to 0.90 (1)Å [OH] and 0.85 (1)Å [NH] and then constrained to refine with the parent atoms with Uiso(H) = 1.5 Ueq(O) and Uiso(H) = 1.2 Ueq(N), see Table 1. The remaining H atoms were positioned geometrically with C-H = 0.93-0.97 Å and included in a riding model approximation with Uiso (H) = 1.2 or 1.5 Ueq (C). A rotating group model was used for the methyl groups.

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. Intramolecular hydrogen bonds are drawn as dashed lines. The H atoms omitted for clarity except those involving in the hydrogen bonds. ...
Fig. 2.
The crystal packing of the title compound viewed down the c-axis, shows linking of molecules along the a-axis through C—H···O hydrogen bonds. Tha dashed lines show interactions.

Crystal data

C30H38N4O2Z = 4
Mr = 486.64F(000) = 1048
Triclinic, P1Dx = 1.168 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.4430 (12) ÅCell parameters from 2502 reflections
b = 12.0251 (12) Åθ = 2.5–30.5°
c = 22.171 (2) ŵ = 0.07 mm1
α = 88.241 (6)°T = 296 K
β = 89.370 (7)°Block, yellow
γ = 65.207 (6)°0.24 × 0.19 × 0.11 mm
V = 2768.2 (5) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer9655 independent reflections
Radiation source: fine-focus sealed tube4485 reflections with I > 2σ(I)
graphiteRint = 0.095
[var phi] and ω scansθmax = 25.0°, θmin = 0.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −13→13
Tmin = 0.983, Tmax = 0.992k = −14→14
44348 measured reflectionsl = −1→26

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.106Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.320H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.1053P)2 + 5.0339P] where P = (Fo2 + 2Fc2)/3
9655 reflections(Δ/σ)max < 0.001
662 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = −0.40 e Å3

Special details

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.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.1771 (4)0.4531 (4)0.2969 (2)0.0672 (14)
H10.20900.51030.29820.101*
O2−0.0627 (4)0.6876 (4)0.34677 (19)0.0623 (12)
H20.01120.69730.34280.093*
O30.4368 (4)0.6831 (4)0.15051 (19)0.0657 (13)
H30.51010.69150.15710.099*
O40.6807 (4)0.4524 (4)0.2030 (2)0.0628 (13)
N10.3133 (5)0.5755 (4)0.2929 (2)0.0443 (12)
N20.1449 (5)0.7137 (4)0.3758 (2)0.0473 (13)
N30.2933 (7)0.1058 (6)0.1759 (3)0.090 (2)
N4−0.3082 (5)0.6070 (5)0.5023 (2)0.0609 (15)
N50.6399 (5)0.7194 (4)0.1182 (2)0.0510 (13)
N60.8132 (5)0.5792 (4)0.2040 (2)0.0480 (13)
H60.75990.54780.19790.058*
N70.1980 (5)0.5983 (5)−0.0011 (2)0.0640 (16)
N80.7927 (6)0.1075 (5)0.3372 (3)0.0712 (17)
C10.2550 (6)0.3818 (6)0.2556 (3)0.0525 (17)
C20.2365 (7)0.2816 (6)0.2369 (3)0.0622 (19)
H2A0.16930.26680.25360.075*
C30.3138 (7)0.2029 (6)0.1944 (3)0.0635 (19)
C40.4164 (7)0.2268 (6)0.1695 (3)0.0625 (19)
H4A0.47030.17530.14080.075*
C50.4356 (7)0.3237 (7)0.1875 (3)0.0614 (19)
H5A0.50330.33740.17060.074*
C60.3577 (6)0.4057 (6)0.2310 (3)0.0453 (15)
C70.3832 (6)0.5038 (6)0.2507 (3)0.0476 (16)
H7A0.45050.51760.23350.057*
C80.3370 (6)0.6713 (5)0.3167 (3)0.0427 (15)
C90.4376 (6)0.7001 (6)0.2999 (3)0.0509 (16)
H9A0.49460.65420.27050.061*
C100.4569 (6)0.7951 (6)0.3252 (3)0.0532 (17)
C110.3742 (7)0.8617 (6)0.3700 (3)0.0580 (18)
C120.2731 (7)0.8316 (6)0.3877 (3)0.0544 (17)
H12A0.21830.87570.41820.065*
C130.2515 (6)0.7399 (5)0.3619 (3)0.0458 (15)
C140.1118 (6)0.7099 (6)0.4310 (3)0.0535 (17)
H14A0.16130.72210.46090.064*
C150.0009 (6)0.6875 (5)0.4493 (3)0.0462 (15)
C16−0.0255 (6)0.6752 (6)0.5095 (3)0.0548 (17)
H16A0.02790.68370.53860.066*
C17−0.1272 (6)0.6510 (6)0.5281 (3)0.0567 (18)
H17A−0.14240.64470.56910.068*
C18−0.2091 (6)0.6355 (6)0.4851 (3)0.0493 (16)
C19−0.1828 (6)0.6490 (6)0.4242 (3)0.0534 (17)
H19A−0.23540.63970.39490.064*
C20−0.0815 (6)0.6756 (5)0.4062 (3)0.0466 (15)
C220.1668 (11)0.0945 (8)0.1939 (4)0.104 (3)
H22A0.09740.17470.19950.124*
H22B0.14170.05320.16300.124*
C230.1964 (13)0.0245 (9)0.2488 (5)0.142 (5)
H23A0.11920.02300.26550.212*
H23B0.23250.06070.27690.212*
H23C0.2575−0.05780.24130.212*
C240.3764 (9)0.0149 (7)0.1341 (4)0.092 (3)
H24A0.3718−0.06250.14350.110*
H24B0.46450.00310.14070.110*
C250.3448 (12)0.0464 (9)0.0695 (5)0.125 (4)
H25A0.4029−0.01860.04530.188*
H25B0.35300.12090.05900.188*
H25C0.25800.05750.06210.188*
C260.5640 (8)0.8280 (8)0.3018 (4)0.082 (2)
H26A0.61270.83530.33520.124*
H26B0.52730.90450.27940.124*
H26C0.61960.76500.27600.124*
C270.3887 (9)0.9674 (7)0.3990 (4)0.095 (3)
H27A0.46790.93710.42130.142*
H27B0.31781.00710.42580.142*
H27C0.38951.02500.36820.142*
C29−0.3988 (6)0.6015 (8)0.4570 (4)0.078 (2)
H29A−0.40920.66200.42510.094*
H29B−0.48210.62320.47590.094*
C30−0.3571 (8)0.4787 (9)0.4297 (4)0.098 (3)
H30A−0.42430.47900.40400.148*
H30B−0.33980.41720.46110.148*
H30C−0.28060.46110.40630.148*
C31−0.3373 (7)0.5918 (6)0.5643 (3)0.065 (2)
H31A−0.25730.55680.58700.078*
H31B−0.37550.53350.56670.078*
C32−0.4263 (9)0.7071 (8)0.5938 (4)0.102 (3)
H32A−0.44300.68830.63450.153*
H32B−0.50580.74310.57170.153*
H32C−0.38720.76380.59410.153*
C330.4194 (6)0.6733 (6)0.0906 (3)0.0504 (16)
C340.3201 (6)0.6427 (6)0.0748 (3)0.0551 (17)
H34A0.26910.63040.10490.066*
C350.2952 (6)0.6301 (6)0.0143 (3)0.0521 (17)
C360.3750 (7)0.6504 (6)−0.0296 (3)0.0614 (19)
H36A0.36020.6441−0.07020.074*
C370.4733 (6)0.6790 (6)−0.0132 (3)0.0570 (18)
H37A0.52450.6912−0.04320.068*
C380.4996 (6)0.6905 (5)0.0467 (3)0.0467 (15)
C390.6070 (6)0.7153 (6)0.0633 (3)0.0558 (17)
H39A0.65560.72920.03260.067*
C400.7476 (6)0.7447 (6)0.1312 (3)0.0495 (16)
C410.7670 (7)0.8394 (7)0.1032 (3)0.068 (2)
H41A0.70970.88540.07310.081*
C420.8680 (8)0.8700 (7)0.1176 (4)0.067 (2)
C430.9524 (7)0.8001 (7)0.1628 (4)0.066 (2)
C440.9355 (6)0.7039 (6)0.1913 (3)0.0554 (17)
H44A0.99400.65670.22080.066*
C450.8327 (6)0.6764 (6)0.1768 (3)0.0481 (16)
C460.8779 (6)0.5096 (6)0.2494 (3)0.0466 (15)
H46A0.94230.52570.26710.056*
C470.8537 (5)0.4122 (6)0.2719 (3)0.0437 (15)
C480.9273 (6)0.3351 (6)0.3189 (3)0.0546 (17)
H48A0.99160.35230.33600.065*
C490.9098 (7)0.2369 (6)0.3407 (3)0.0614 (19)
H49A0.96200.18870.37190.074*
C500.8121 (6)0.2061 (6)0.3164 (3)0.0522 (16)
C510.7368 (6)0.2830 (6)0.2700 (3)0.0536 (17)
H51A0.67230.26550.25330.064*
C520.7536 (6)0.3841 (6)0.2475 (3)0.0466 (15)
C540.1720 (7)0.5812 (6)−0.0635 (3)0.066 (2)
H54A0.13550.5216−0.06430.079*
H54B0.25250.5484−0.08550.079*
C550.0812 (9)0.6977 (8)−0.0946 (4)0.101 (3)
H55A0.05840.6796−0.13340.151*
H55B0.12230.7526−0.09960.151*
H55C0.00500.7356−0.07070.151*
C560.1057 (7)0.5896 (8)0.0441 (4)0.076 (2)
H56A0.02390.60930.02420.091*
H56B0.09160.65040.07440.091*
C570.1492 (8)0.4652 (9)0.0751 (4)0.094 (3)
H57A0.08620.46680.10440.140*
H57B0.23020.44460.09480.140*
H57C0.15890.40490.04570.140*
C580.8813 (11)0.9777 (8)0.0858 (5)0.120 (4)
H58A0.88591.03260.11530.180*
H58B0.80801.02020.06010.180*
H58C0.95830.94840.06200.180*
C591.0633 (8)0.8279 (8)0.1837 (4)0.091 (3)
H59A1.10800.84070.14920.137*
H59B1.12160.76010.20790.137*
H59C1.03020.90030.20720.137*
C610.8788 (9)0.0184 (7)0.3812 (4)0.085 (3)
H61A0.96420.01630.37720.102*
H61B0.8849−0.06240.37260.102*
C620.8333 (11)0.0484 (9)0.4446 (4)0.123 (4)
H62A0.8955−0.00870.47200.184*
H62B0.75240.04320.44980.184*
H62C0.82280.13000.45270.184*
C630.6915 (8)0.0789 (7)0.3124 (3)0.076 (2)
H63A0.61650.15440.30320.092*
H63B0.66660.03210.34210.092*
C640.7357 (11)0.0071 (8)0.2564 (4)0.110 (3)
H64A0.6669−0.00900.24040.165*
H64B0.8079−0.06910.26580.165*
H64C0.76090.05320.22700.165*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.055 (3)0.077 (3)0.085 (4)−0.041 (3)0.024 (3)−0.035 (3)
O20.059 (3)0.087 (3)0.051 (3)−0.041 (3)0.000 (2)−0.004 (2)
O30.061 (3)0.091 (4)0.056 (3)−0.042 (3)−0.002 (2)−0.009 (3)
O40.051 (3)0.076 (3)0.069 (3)−0.035 (3)−0.020 (2)0.018 (3)
N10.045 (3)0.049 (3)0.045 (3)−0.025 (3)0.002 (2)−0.009 (3)
N20.047 (3)0.048 (3)0.052 (3)−0.025 (3)0.005 (3)−0.011 (3)
N30.100 (6)0.078 (5)0.116 (6)−0.058 (4)0.027 (4)−0.043 (4)
N40.043 (3)0.083 (4)0.061 (4)−0.031 (3)0.001 (3)0.008 (3)
N50.044 (3)0.046 (3)0.067 (4)−0.022 (3)0.000 (3)−0.003 (3)
N60.048 (3)0.045 (3)0.059 (4)−0.028 (3)0.001 (3)−0.007 (3)
N70.049 (3)0.084 (4)0.060 (4)−0.028 (3)−0.004 (3)−0.015 (3)
N80.080 (4)0.049 (4)0.094 (5)−0.037 (3)0.000 (4)0.007 (3)
C10.047 (4)0.053 (4)0.060 (4)−0.023 (3)0.005 (3)−0.018 (3)
C20.066 (5)0.058 (5)0.075 (5)−0.039 (4)0.018 (4)−0.018 (4)
C30.066 (5)0.055 (4)0.078 (5)−0.033 (4)0.001 (4)−0.016 (4)
C40.054 (4)0.065 (5)0.066 (5)−0.021 (4)0.012 (4)−0.025 (4)
C50.052 (4)0.077 (5)0.062 (5)−0.033 (4)0.013 (4)−0.019 (4)
C60.036 (3)0.052 (4)0.049 (4)−0.020 (3)0.001 (3)−0.006 (3)
C70.047 (4)0.058 (4)0.047 (4)−0.030 (3)−0.003 (3)0.002 (3)
C80.041 (4)0.043 (4)0.052 (4)−0.025 (3)−0.004 (3)0.002 (3)
C90.050 (4)0.047 (4)0.065 (4)−0.030 (3)0.002 (3)−0.004 (3)
C100.049 (4)0.058 (4)0.063 (4)−0.034 (3)−0.003 (3)0.004 (4)
C110.070 (5)0.049 (4)0.069 (5)−0.038 (4)−0.011 (4)−0.001 (4)
C120.066 (5)0.046 (4)0.060 (4)−0.032 (4)0.008 (3)−0.007 (3)
C130.047 (4)0.043 (4)0.054 (4)−0.025 (3)−0.007 (3)−0.001 (3)
C140.041 (4)0.047 (4)0.069 (5)−0.015 (3)−0.010 (3)0.000 (3)
C150.041 (4)0.042 (4)0.053 (4)−0.015 (3)0.000 (3)−0.007 (3)
C160.054 (4)0.061 (4)0.053 (4)−0.028 (4)−0.005 (3)−0.004 (3)
C170.057 (4)0.067 (5)0.050 (4)−0.029 (4)0.006 (3)−0.005 (3)
C180.042 (4)0.048 (4)0.054 (4)−0.016 (3)0.003 (3)0.003 (3)
C190.042 (4)0.060 (4)0.062 (5)−0.025 (3)−0.005 (3)−0.001 (3)
C200.043 (4)0.050 (4)0.045 (4)−0.017 (3)0.003 (3)−0.006 (3)
C220.173 (11)0.065 (6)0.081 (6)−0.057 (6)−0.044 (7)0.002 (5)
C230.198 (13)0.096 (8)0.131 (10)−0.062 (8)−0.073 (9)0.011 (7)
C240.117 (8)0.057 (5)0.106 (7)−0.040 (5)0.003 (6)−0.027 (5)
C250.164 (11)0.097 (8)0.109 (9)−0.047 (7)−0.002 (8)−0.022 (6)
C260.073 (5)0.088 (6)0.113 (7)−0.060 (5)0.005 (5)−0.012 (5)
C270.111 (7)0.080 (6)0.122 (7)−0.069 (6)0.006 (6)−0.024 (5)
C290.033 (4)0.120 (7)0.081 (6)−0.033 (4)−0.005 (4)0.023 (5)
C300.075 (6)0.134 (9)0.110 (7)−0.066 (6)−0.003 (5)−0.018 (6)
C310.056 (4)0.063 (5)0.070 (5)−0.018 (4)0.018 (4)−0.002 (4)
C320.084 (6)0.089 (7)0.111 (7)−0.015 (5)0.027 (5)−0.011 (5)
C330.045 (4)0.054 (4)0.049 (4)−0.016 (3)−0.004 (3)−0.008 (3)
C340.045 (4)0.063 (4)0.057 (4)−0.022 (3)0.007 (3)−0.009 (3)
C350.043 (4)0.053 (4)0.057 (4)−0.017 (3)−0.006 (3)−0.005 (3)
C360.059 (5)0.070 (5)0.052 (4)−0.024 (4)−0.008 (4)−0.003 (4)
C370.051 (4)0.065 (5)0.053 (4)−0.022 (4)−0.001 (3)0.006 (3)
C380.042 (4)0.038 (4)0.057 (4)−0.014 (3)−0.003 (3)−0.002 (3)
C390.058 (4)0.048 (4)0.058 (5)−0.020 (3)0.002 (4)−0.004 (3)
C400.052 (4)0.043 (4)0.059 (4)−0.026 (3)0.008 (3)−0.013 (3)
C410.071 (5)0.061 (5)0.078 (5)−0.034 (4)0.008 (4)−0.002 (4)
C420.082 (6)0.060 (5)0.080 (5)−0.050 (4)0.011 (4)−0.008 (4)
C430.066 (5)0.052 (4)0.097 (6)−0.041 (4)0.015 (4)−0.021 (4)
C440.055 (4)0.057 (4)0.062 (4)−0.030 (4)0.007 (3)−0.015 (3)
C450.042 (4)0.043 (4)0.067 (4)−0.026 (3)0.007 (3)−0.009 (3)
C460.044 (4)0.054 (4)0.050 (4)−0.028 (3)−0.002 (3)−0.009 (3)
C470.030 (3)0.051 (4)0.052 (4)−0.020 (3)−0.001 (3)−0.007 (3)
C480.051 (4)0.066 (5)0.055 (4)−0.031 (4)−0.008 (3)−0.007 (4)
C490.054 (4)0.060 (5)0.072 (5)−0.027 (4)−0.009 (4)0.004 (4)
C500.052 (4)0.051 (4)0.057 (4)−0.025 (3)0.007 (3)−0.006 (3)
C510.047 (4)0.048 (4)0.068 (5)−0.022 (3)−0.010 (3)0.002 (3)
C520.038 (4)0.051 (4)0.050 (4)−0.018 (3)−0.001 (3)−0.002 (3)
C540.057 (4)0.070 (5)0.063 (5)−0.017 (4)−0.019 (4)−0.007 (4)
C550.095 (7)0.083 (6)0.101 (7)−0.014 (5)−0.031 (5)0.012 (5)
C560.040 (4)0.105 (7)0.086 (6)−0.031 (4)0.003 (4)−0.028 (5)
C570.072 (6)0.120 (8)0.096 (7)−0.048 (6)0.005 (5)−0.005 (6)
C580.144 (10)0.081 (7)0.164 (10)−0.076 (7)0.006 (8)0.011 (6)
C590.082 (6)0.087 (6)0.134 (8)−0.064 (5)0.011 (5)−0.024 (5)
C610.102 (7)0.052 (5)0.100 (7)−0.030 (5)−0.008 (5)0.009 (5)
C620.163 (11)0.105 (8)0.085 (7)−0.043 (7)−0.029 (7)0.021 (6)
C630.111 (7)0.074 (5)0.072 (5)−0.066 (5)0.024 (5)−0.009 (4)
C640.153 (10)0.084 (6)0.108 (8)−0.062 (7)0.038 (7)−0.030 (6)

Geometric parameters (Å, °)

O1—C11.326 (7)C27—H27B0.9600
O1—H10.9059C27—H27C0.9600
O2—C201.346 (7)C29—C301.495 (11)
O2—H20.9029C29—H29A0.9700
O3—C331.361 (7)C29—H29B0.9700
O3—H30.8998C30—H30A0.9600
O4—C521.319 (7)C30—H30B0.9600
N1—C71.309 (7)C30—H30C0.9600
N1—C81.407 (7)C31—C321.498 (10)
N2—C141.283 (8)C31—H31A0.9700
N2—C131.411 (7)C31—H31B0.9700
N3—C31.359 (8)C32—H32A0.9600
N3—C241.459 (10)C32—H32B0.9600
N3—C221.556 (12)C32—H32C0.9600
N4—C181.363 (8)C33—C341.384 (9)
N4—C311.435 (8)C33—C381.401 (9)
N4—C291.475 (9)C34—C351.401 (9)
N5—C391.287 (8)C34—H34A0.9300
N5—C401.423 (8)C35—C361.411 (9)
N6—C461.307 (7)C36—C371.363 (9)
N6—C451.397 (7)C36—H36A0.9300
N6—H60.8542C37—C381.388 (8)
N7—C351.368 (8)C37—H37A0.9300
N7—C541.455 (8)C38—C391.434 (9)
N7—C561.481 (9)C39—H39A0.9300
N8—C501.362 (8)C40—C411.378 (9)
N8—C631.458 (9)C40—C451.394 (9)
N8—C611.463 (10)C41—C421.394 (10)
C1—C21.384 (8)C41—H41A0.9300
C1—C61.422 (8)C42—C431.390 (10)
C2—C31.379 (9)C42—C581.517 (10)
C2—H2A0.9300C43—C441.384 (9)
C3—C41.422 (9)C43—C591.521 (10)
C4—C51.346 (9)C44—C451.393 (8)
C4—H4A0.9300C44—H44A0.9300
C5—C61.413 (8)C46—C471.390 (8)
C5—H5A0.9300C46—H46A0.9300
C6—C71.410 (8)C47—C481.400 (8)
C7—H7A0.9300C47—C521.438 (8)
C8—C91.379 (8)C48—C491.353 (9)
C8—C131.413 (8)C48—H48A0.9300
C9—C101.385 (8)C49—C501.432 (9)
C9—H9A0.9300C49—H49A0.9300
C10—C111.385 (9)C50—C511.397 (9)
C10—C261.519 (9)C51—C521.386 (8)
C11—C121.398 (9)C51—H51A0.9300
C11—C271.511 (9)C54—C551.501 (10)
C12—C131.369 (8)C54—H54A0.9700
C12—H12A0.9300C54—H54B0.9700
C14—C151.455 (9)C55—H55A0.9600
C14—H14A0.9300C55—H55B0.9600
C15—C161.382 (8)C55—H55C0.9600
C15—C201.402 (8)C56—C571.509 (11)
C16—C171.369 (9)C56—H56A0.9700
C16—H16A0.9300C56—H56B0.9700
C17—C181.412 (9)C57—H57A0.9600
C17—H17A0.9300C57—H57B0.9600
C18—C191.400 (9)C57—H57C0.9600
C19—C201.378 (8)C58—H58A0.9600
C19—H19A0.9300C58—H58B0.9600
C22—C231.420 (12)C58—H58C0.9600
C22—H22A0.9700C59—H59A0.9600
C22—H22B0.9700C59—H59B0.9600
C23—H23A0.9600C59—H59C0.9600
C23—H23B0.9600C61—C621.495 (12)
C23—H23C0.9600C61—H61A0.9700
C24—C251.480 (12)C61—H61B0.9700
C24—H24A0.9700C62—H62A0.9600
C24—H24B0.9700C62—H62B0.9600
C25—H25A0.9600C62—H62C0.9600
C25—H25B0.9600C63—C641.492 (10)
C25—H25C0.9600C63—H63A0.9700
C26—H26A0.9600C63—H63B0.9700
C26—H26B0.9600C64—H64A0.9600
C26—H26C0.9600C64—H64B0.9600
C27—H27A0.9600C64—H64C0.9600
C1—O1—H199.1C32—C31—H31A108.5
C20—O2—H2107.2N4—C31—H31B108.5
C33—O3—H3111.0C32—C31—H31B108.5
C7—N1—C8123.9 (5)H31A—C31—H31B107.5
C14—N2—C13119.7 (5)C31—C32—H32A109.5
C3—N3—C24124.4 (7)C31—C32—H32B109.5
C3—N3—C22119.8 (7)H32A—C32—H32B109.5
C24—N3—C22115.5 (6)C31—C32—H32C109.5
C18—N4—C31122.9 (6)H32A—C32—H32C109.5
C18—N4—C29120.4 (6)H32B—C32—H32C109.5
C31—N4—C29116.5 (6)O3—C33—C34117.0 (6)
C39—N5—C40120.7 (6)O3—C33—C38121.9 (6)
C46—N6—C45126.5 (5)C34—C33—C38121.0 (6)
C46—N6—H699.8C33—C34—C35121.1 (6)
C45—N6—H6133.7C33—C34—H34A119.4
C35—N7—C54122.2 (6)C35—C34—H34A119.4
C35—N7—C56121.9 (6)N7—C35—C34121.0 (6)
C54—N7—C56115.7 (6)N7—C35—C36121.8 (6)
C50—N8—C63121.2 (6)C34—C35—C36117.2 (6)
C50—N8—C61122.3 (6)C37—C36—C35121.0 (6)
C63—N8—C61116.2 (6)C37—C36—H36A119.5
O1—C1—C2119.1 (6)C35—C36—H36A119.5
O1—C1—C6121.1 (5)C36—C37—C38122.3 (6)
C2—C1—C6119.8 (6)C36—C37—H37A118.9
C3—C2—C1122.5 (6)C38—C37—H37A118.9
C3—C2—H2A118.7C37—C38—C33117.4 (6)
C1—C2—H2A118.7C37—C38—C39121.6 (6)
N3—C3—C2121.8 (7)C33—C38—C39121.0 (6)
N3—C3—C4120.4 (7)N5—C39—C38123.9 (6)
C2—C3—C4117.9 (6)N5—C39—H39A118.1
C5—C4—C3120.2 (6)C38—C39—H39A118.1
C5—C4—H4A119.9C41—C40—C45118.3 (6)
C3—C4—H4A119.9C41—C40—N5122.6 (6)
C4—C5—C6123.0 (6)C45—C40—N5119.0 (6)
C4—C5—H5A118.5C40—C41—C42123.5 (7)
C6—C5—H5A118.5C40—C41—H41A118.2
C7—C6—C5121.8 (6)C42—C41—H41A118.2
C7—C6—C1121.5 (6)C43—C42—C41117.2 (7)
C5—C6—C1116.6 (6)C43—C42—C58122.2 (7)
N1—C7—C6120.9 (6)C41—C42—C58120.5 (8)
N1—C7—H7A119.5C44—C43—C42120.3 (6)
C6—C7—H7A119.5C44—C43—C59117.8 (8)
C9—C8—N1124.8 (6)C42—C43—C59121.8 (7)
C9—C8—C13118.8 (5)C43—C44—C45121.3 (7)
N1—C8—C13116.3 (5)C43—C44—H44A119.4
C8—C9—C10122.4 (6)C45—C44—H44A119.4
C8—C9—H9A118.8C44—C45—C40119.2 (6)
C10—C9—H9A118.8C44—C45—N6123.0 (6)
C9—C10—C11119.0 (6)C40—C45—N6117.7 (5)
C9—C10—C26119.9 (6)N6—C46—C47122.0 (5)
C11—C10—C26121.0 (6)N6—C46—H46A119.0
C10—C11—C12118.7 (6)C47—C46—H46A119.0
C10—C11—C27121.7 (7)C46—C47—C48121.5 (5)
C12—C11—C27119.5 (7)C46—C47—C52121.8 (6)
C13—C12—C11122.6 (6)C48—C47—C52116.7 (6)
C13—C12—H12A118.7C49—C48—C47123.3 (6)
C11—C12—H12A118.7C49—C48—H48A118.3
C12—C13—N2123.7 (6)C47—C48—H48A118.3
C12—C13—C8118.4 (6)C48—C49—C50120.9 (6)
N2—C13—C8117.8 (5)C48—C49—H49A119.5
N2—C14—C15123.4 (6)C50—C49—H49A119.5
N2—C14—H14A118.3N8—C50—C51121.3 (6)
C15—C14—H14A118.3N8—C50—C49122.2 (6)
C16—C15—C20117.9 (6)C51—C50—C49116.5 (6)
C16—C15—C14121.3 (6)C52—C51—C50123.0 (6)
C20—C15—C14120.8 (6)C52—C51—H51A118.5
C17—C16—C15122.6 (6)C50—C51—H51A118.5
C17—C16—H16A118.7O4—C52—C51120.3 (6)
C15—C16—H16A118.7O4—C52—C47120.1 (6)
C16—C17—C18120.2 (6)C51—C52—C47119.6 (6)
C16—C17—H17A119.9N7—C54—C55113.0 (6)
C18—C17—H17A119.9N7—C54—H54A109.0
N4—C18—C19121.5 (6)C55—C54—H54A109.0
N4—C18—C17121.4 (6)N7—C54—H54B109.0
C19—C18—C17117.1 (6)C55—C54—H54B109.0
C20—C19—C18122.1 (6)H54A—C54—H54B107.8
C20—C19—H19A119.0C54—C55—H55A109.5
C18—C19—H19A119.0C54—C55—H55B109.5
O2—C20—C19118.6 (5)H55A—C55—H55B109.5
O2—C20—C15121.3 (6)C54—C55—H55C109.5
C19—C20—C15120.1 (6)H55A—C55—H55C109.5
C23—C22—N3104.9 (9)H55B—C55—H55C109.5
C23—C22—H22A110.8N7—C56—C57114.0 (6)
N3—C22—H22A110.8N7—C56—H56A108.8
C23—C22—H22B110.8C57—C56—H56A108.8
N3—C22—H22B110.8N7—C56—H56B108.8
H22A—C22—H22B108.8C57—C56—H56B108.8
C22—C23—H23A109.5H56A—C56—H56B107.7
C22—C23—H23B109.5C56—C57—H57A109.5
H23A—C23—H23B109.5C56—C57—H57B109.5
C22—C23—H23C109.5H57A—C57—H57B109.5
H23A—C23—H23C109.5C56—C57—H57C109.5
H23B—C23—H23C109.5H57A—C57—H57C109.5
N3—C24—C25115.0 (8)H57B—C57—H57C109.5
N3—C24—H24A108.5C42—C58—H58A109.5
C25—C24—H24A108.5C42—C58—H58B109.5
N3—C24—H24B108.5H58A—C58—H58B109.5
C25—C24—H24B108.5C42—C58—H58C109.5
H24A—C24—H24B107.5H58A—C58—H58C109.5
C24—C25—H25A109.5H58B—C58—H58C109.5
C24—C25—H25B109.5C43—C59—H59A109.5
H25A—C25—H25B109.5C43—C59—H59B109.5
C24—C25—H25C109.5H59A—C59—H59B109.5
H25A—C25—H25C109.5C43—C59—H59C109.5
H25B—C25—H25C109.5H59A—C59—H59C109.5
C10—C26—H26A109.5H59B—C59—H59C109.5
C10—C26—H26B109.5N8—C61—C62112.3 (7)
H26A—C26—H26B109.5N8—C61—H61A109.1
C10—C26—H26C109.5C62—C61—H61A109.1
H26A—C26—H26C109.5N8—C61—H61B109.1
H26B—C26—H26C109.5C62—C61—H61B109.1
C11—C27—H27A109.5H61A—C61—H61B107.9
C11—C27—H27B109.5C61—C62—H62A109.5
H27A—C27—H27B109.5C61—C62—H62B109.5
C11—C27—H27C109.5H62A—C62—H62B109.5
H27A—C27—H27C109.5C61—C62—H62C109.5
H27B—C27—H27C109.5H62A—C62—H62C109.5
N4—C29—C30113.8 (6)H62B—C62—H62C109.5
N4—C29—H29A108.8N8—C63—C64111.0 (7)
C30—C29—H29A108.8N8—C63—H63A109.4
N4—C29—H29B108.8C64—C63—H63A109.4
C30—C29—H29B108.8N8—C63—H63B109.4
H29A—C29—H29B107.7C64—C63—H63B109.4
C29—C30—H30A109.5H63A—C63—H63B108.0
C29—C30—H30B109.5C63—C64—H64A109.5
H30A—C30—H30B109.5C63—C64—H64B109.5
C29—C30—H30C109.5H64A—C64—H64B109.5
H30A—C30—H30C109.5C63—C64—H64C109.5
H30B—C30—H30C109.5H64A—C64—H64C109.5
N4—C31—C32114.9 (6)H64B—C64—H64C109.5
N4—C31—H31A108.5
O1—C1—C2—C3−179.7 (7)O3—C33—C34—C35−179.8 (6)
C6—C1—C2—C3−0.5 (11)C38—C33—C34—C35−1.1 (10)
C24—N3—C3—C2−175.9 (8)C54—N7—C35—C34−178.3 (6)
C22—N3—C3—C211.0 (12)C56—N7—C35—C347.1 (10)
C24—N3—C3—C44.8 (13)C54—N7—C35—C361.1 (10)
C22—N3—C3—C4−168.4 (7)C56—N7—C35—C36−173.5 (7)
C1—C2—C3—N3−179.1 (7)C33—C34—C35—N7179.1 (6)
C1—C2—C3—C40.3 (11)C33—C34—C35—C36−0.3 (9)
N3—C3—C4—C5179.3 (7)N7—C35—C36—C37−178.4 (6)
C2—C3—C4—C5−0.1 (11)C34—C35—C36—C371.1 (10)
C3—C4—C5—C60.0 (11)C35—C36—C37—C38−0.5 (10)
C4—C5—C6—C7177.5 (6)C36—C37—C38—C33−0.9 (10)
C4—C5—C6—C1−0.3 (10)C36—C37—C38—C39177.2 (6)
O1—C1—C6—C71.9 (10)O3—C33—C38—C37−179.7 (6)
C2—C1—C6—C7−177.3 (6)C34—C33—C38—C371.7 (9)
O1—C1—C6—C5179.6 (6)O3—C33—C38—C392.2 (9)
C2—C1—C6—C50.5 (9)C34—C33—C38—C39−176.4 (6)
C8—N1—C7—C6176.9 (5)C40—N5—C39—C38−179.9 (6)
C5—C6—C7—N1−177.0 (6)C37—C38—C39—N5−175.6 (6)
C1—C6—C7—N10.6 (9)C33—C38—C39—N52.4 (10)
C7—N1—C8—C9−1.5 (9)C39—N5—C40—C4147.0 (9)
C7—N1—C8—C13179.8 (6)C39—N5—C40—C45−137.3 (6)
N1—C8—C9—C10−179.5 (6)C45—C40—C41—C420.6 (10)
C13—C8—C9—C10−0.9 (9)N5—C40—C41—C42176.4 (6)
C8—C9—C10—C111.7 (10)C40—C41—C42—C430.0 (11)
C8—C9—C10—C26−175.8 (6)C40—C41—C42—C58−178.5 (7)
C9—C10—C11—C12−0.8 (10)C41—C42—C43—C440.4 (11)
C26—C10—C11—C12176.7 (6)C58—C42—C43—C44178.9 (7)
C9—C10—C11—C27−179.2 (7)C41—C42—C43—C59−177.9 (7)
C26—C10—C11—C27−1.8 (11)C58—C42—C43—C590.6 (12)
C10—C11—C12—C13−0.9 (10)C42—C43—C44—C45−1.5 (10)
C27—C11—C12—C13177.6 (7)C59—C43—C44—C45176.9 (6)
C11—C12—C13—N2−175.2 (6)C43—C44—C45—C402.1 (9)
C11—C12—C13—C81.7 (10)C43—C44—C45—N6179.2 (6)
C14—N2—C13—C12−44.7 (9)C41—C40—C45—C44−1.6 (9)
C14—N2—C13—C8138.4 (6)N5—C40—C45—C44−177.6 (5)
C9—C8—C13—C12−0.8 (9)C41—C40—C45—N6−178.8 (6)
N1—C8—C13—C12178.0 (5)N5—C40—C45—N65.2 (8)
C9—C8—C13—N2176.3 (5)C46—N6—C45—C447.0 (9)
N1—C8—C13—N2−4.9 (8)C46—N6—C45—C40−175.9 (6)
C13—N2—C14—C15177.9 (5)C45—N6—C46—C47−177.8 (6)
N2—C14—C15—C16175.1 (6)N6—C46—C47—C48177.3 (6)
N2—C14—C15—C20−3.7 (9)N6—C46—C47—C52−1.5 (9)
C20—C15—C16—C170.6 (10)C46—C47—C48—C49−177.6 (6)
C14—C15—C16—C17−178.3 (6)C52—C47—C48—C491.3 (10)
C15—C16—C17—C181.0 (10)C47—C48—C49—C50−0.3 (11)
C31—N4—C18—C19179.6 (6)C63—N8—C50—C51−0.8 (10)
C29—N4—C18—C19−6.1 (10)C61—N8—C50—C51173.3 (7)
C31—N4—C18—C170.6 (10)C63—N8—C50—C49179.1 (6)
C29—N4—C18—C17174.9 (6)C61—N8—C50—C49−6.7 (10)
C16—C17—C18—N4177.6 (6)C48—C49—C50—N8179.6 (6)
C16—C17—C18—C19−1.5 (9)C48—C49—C50—C51−0.4 (10)
N4—C18—C19—C20−178.8 (6)N8—C50—C51—C52−179.9 (6)
C17—C18—C19—C200.3 (9)C49—C50—C51—C520.1 (10)
C18—C19—C20—O2−179.7 (6)C50—C51—C52—O4179.0 (6)
C18—C19—C20—C151.4 (10)C50—C51—C52—C470.9 (10)
C16—C15—C20—O2179.3 (6)C46—C47—C52—O4−0.8 (9)
C14—C15—C20—O2−1.8 (9)C48—C47—C52—O4−179.7 (6)
C16—C15—C20—C19−1.8 (9)C46—C47—C52—C51177.4 (6)
C14—C15—C20—C19177.1 (6)C48—C47—C52—C51−1.5 (9)
C3—N3—C22—C23−91.3 (9)C35—N7—C54—C55−88.1 (9)
C24—N3—C22—C2394.9 (9)C56—N7—C54—C5586.8 (9)
C3—N3—C24—C25−87.8 (11)C35—N7—C56—C57−88.4 (8)
C22—N3—C24—C2585.7 (10)C54—N7—C56—C5796.7 (7)
C18—N4—C29—C3088.3 (8)C50—N8—C61—C6293.5 (9)
C31—N4—C29—C30−97.1 (8)C63—N8—C61—C62−92.1 (9)
C18—N4—C31—C3288.0 (9)C50—N8—C63—C6483.9 (9)
C29—N4—C31—C32−86.5 (9)C61—N8—C63—C64−90.6 (8)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.911.682.553 (7)160
O2—H2···N20.901.792.613 (8)150
O3—H3···N50.901.852.627 (8)143
N6—H6···O40.851.742.562 (7)162
C7—H7A···O40.932.503.360 (9)153
C46—H46A···O1i0.932.543.373 (9)149

Symmetry codes: (i) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2737).

References

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