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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1454.
Published online 2010 May 26. doi:  10.1107/S1600536810018702
PMCID: PMC2979579

5-Butyl­amino-2-[2-(dimethyl­amino)eth­yl]-1H-benz[de]isoquinoline-1,3(2H)-dione

Abstract

The title compound, C20H25N3O2, is a new amonafide analogue, which exhibits anti­tumor activity. The asymmetric unit contains two mol­ecules with similar conformations for the substituted aliphatic chains. The two independent mol­ecules form dmers through N—H(...)N hydrogen bonds. The crystal structure is stabilized via π–π stacking inter­actions, the shortest centroid–centroid separation between six-membered rings being 3.673 (2) Å.

Related literature

For general background to amonafide and its anti­tumour activity, see: Braña et al. (1981 [triangle], 2001 [triangle]); Braña & Ramos (2001 [triangle]); Ratain et al. (1991 [triangle], 1993 [triangle]). For the synthesis of amonafide analogues, see: Xie et al. (2009 [triangle]).

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Object name is e-66-o1454-scheme1.jpg

Experimental

Crystal data

  • C20H25N3O2
  • M r = 339.43
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1454-efi1.jpg
  • a = 11.5978 (12) Å
  • b = 12.5362 (13) Å
  • c = 14.3721 (16) Å
  • α = 72.329 (2)°
  • β = 70.599 (2)°
  • γ = 70.759 (2)°
  • V = 1816.1 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.36 × 0.33 × 0.08 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.739, T max = 1.000
  • 10049 measured reflections
  • 7018 independent reflections
  • 3025 reflections with I > 2σ(I)
  • R int = 0.059

Refinement

  • R[F 2 > 2σ(F 2)] = 0.068
  • wR(F 2) = 0.175
  • S = 0.86
  • 7018 reflections
  • 466 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810018702/bh2282sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018702/bh2282Isup2.hkl

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

Acknowledgments

The author is grateful for the support of the Scientific Research Foundation of Huaqiao University (09BS406) and the State Key Laboratory of Oncology in South China.

supplementary crystallographic information

Comment

Amonafide (Braña et al., 1981, 2001; Braña & Ramos, 2001) was the first compound of the naphthalimide family that reached the clinical trial stage and exhibited excellent antitumour activity against advanced breast cancer. However, in the clinical studies, it was found that amonafide was easily metabolized to N-acetyl-amonafide by enzyme N-acetyltransferase, which caused a high-variable, unpredictable toxicity (Ratain et al., 1991, 1993). In order to reduce the unpredictable toxic effect of the amonafide, we synthesized a series of amonafide analogues (Xie et al., 2009) involved the title compound, which is being reported in this article.

The molecular structure of the title compound is shown in Fig. 1. The asymmetric unit contains two independent molecules, and it is observed that the butyl chains do not present the common all-trans conformation. This uncommon feature could be attributed to formation of intermolecular N—H···N hydrogen bonds in the asymmetric unit [N2··· N6 and N3···N5], which involve the butyl and the dimethylamino groups, and reduce the intermolecular hindrance. The crystal structure is stabilized via π-π stacking interactions [centroid-centroid separations: 3.673 (2) and 3.693 (2) Å] and intermolecular N—H···N hydrogen bonds, which lead to a supramolecular network of stacked molecules in 1D chains (Fig. 2). Apart from the functional groups butylamino and N,N-dimethylamino-ethylamino, the central 1,8-naphthalimide fused rings system is almost planar.

Experimental

A mixture of 3-bromide-1,8-naphthalic anhydride (277 mg, 1.0 mmol) and N,N-dimethylethyldiamine (92 mg, 1.0 mmol) was refluxed in EtOH (15 ml) for 2 h, to give the intermediate 5-bromo-2-[2-(dimethylamino)ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione. This intermediate (174 mg, 0.5 mmol), CuI (9 mg, 0.05 mmol), proline (11 mg, 0.1 mmol), Cs2CO3 (244 mg, 0.75 mmol) and n-butylamine (0.75 mmol) in dry DMSO (2 ml) were mixed and stirred at 383 K for 9 h under nitrogen. The crude products were purified by chromatography on silica gel with a mixture of CH2Cl2 and MeOH as eluent. Single crystals of the title compound were obtained from a CH2Cl2—MeOH solution.

Refinement

C-bonded H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic), 0.97 (methylene) or 0.96 Å (methyl). Isotropic displacement parameters were computed as Uiso(H) = 1.2Ueq(carrier C) for methylene and aromatic H atoms, and Uiso(H) = 1.5Ueq(carrier C) for methyl groups. Amine H atoms H2 and H5 were found in a difference map and refined freely.

Figures

Fig. 1.
The structure of the title compound showing 30% probability displacement ellipsoids and the atom labeling scheme. H atoms are omitted for clarity.
Fig. 2.
Packing diagram with H bonds indicated by dashed lines.

Crystal data

C20H25N3O2Z = 4
Mr = 339.43F(000) = 728
Triclinic, P1Dx = 1.241 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.5978 (12) ÅCell parameters from 1325 reflections
b = 12.5362 (13) Åθ = 5.2–49.0°
c = 14.3721 (16) ŵ = 0.08 mm1
α = 72.329 (2)°T = 293 K
β = 70.599 (2)°Prismatic, yellow
γ = 70.759 (2)°0.36 × 0.33 × 0.08 mm
V = 1816.1 (3) Å3

Data collection

Bruker SMART APEX CCD area-detector diffractometer7018 independent reflections
Radiation source: fine-focus sealed tube3025 reflections with I > 2σ(I)
graphiteRint = 0.059
[var phi] and ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −14→13
Tmin = 0.739, Tmax = 1.000k = −15→11
10049 measured reflectionsl = −17→16

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.175w = 1/[σ2(Fo2) + (0.0653P)2] where P = (Fo2 + 2Fc2)/3
S = 0.86(Δ/σ)max < 0.001
7018 reflectionsΔρmax = 0.34 e Å3
466 parametersΔρmin = −0.25 e Å3
3 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.0040 (10)
Primary atom site location: structure-invariant direct methods

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

xyzUiso*/Ueq
O10.6424 (3)0.8935 (2)0.2061 (2)0.0695 (9)
O20.4583 (2)0.7887 (2)0.54144 (19)0.0625 (8)
O30.8585 (3)0.6222 (3)0.8127 (2)0.0754 (9)
O40.6754 (3)0.5191 (3)0.6307 (2)0.0700 (9)
N10.5553 (3)0.8357 (3)0.3739 (2)0.0481 (8)
N20.6845 (3)0.9030 (3)0.7247 (3)0.0592 (10)
N30.6185 (3)0.6109 (3)0.2983 (2)0.0537 (9)
N40.7643 (3)0.5748 (3)0.7207 (2)0.0518 (8)
N50.8927 (4)0.6479 (3)0.2640 (3)0.0665 (11)
N60.5323 (3)0.7148 (3)0.8571 (2)0.0537 (9)
C10.6412 (4)0.8876 (3)0.2925 (3)0.0508 (10)
C20.5400 (4)0.8308 (3)0.4763 (3)0.0480 (10)
C30.6272 (3)0.8762 (3)0.4991 (3)0.0394 (9)
C40.7179 (3)0.9258 (3)0.4200 (3)0.0416 (9)
C50.7264 (3)0.9327 (3)0.3189 (3)0.0461 (10)
C60.8156 (4)0.9811 (3)0.2421 (3)0.0563 (11)
H60.82120.98550.17500.068*
C70.8974 (4)1.0234 (4)0.2660 (3)0.0628 (12)
H70.95731.05630.21440.075*
C80.8902 (3)1.0169 (3)0.3642 (3)0.0578 (11)
H80.94581.04520.37840.069*
C90.8004 (3)0.9683 (3)0.4447 (3)0.0453 (10)
C100.7902 (3)0.9603 (3)0.5474 (3)0.0510 (10)
H100.84390.98900.56350.061*
C110.7023 (3)0.9107 (3)0.6237 (3)0.0453 (10)
C120.6205 (3)0.8696 (3)0.5963 (3)0.0455 (10)
H120.55990.83680.64720.055*
C130.7608 (4)0.9397 (4)0.7643 (3)0.0675 (13)
H13A0.77531.01370.72320.081*
H13B0.84220.88370.76180.081*
C140.6929 (5)0.9512 (5)0.8749 (3)0.108 (2)
H14A0.60630.99570.87750.130*
H14B0.69030.87440.91630.130*
C150.7481 (6)1.0049 (6)0.9201 (4)0.123 (2)
H15A0.83360.95850.92020.148*
H15B0.70031.00240.99010.148*
C160.7529 (6)1.1257 (5)0.8708 (4)0.129 (2)
H16A0.80981.12820.80460.194*
H16B0.78211.15570.91050.194*
H16C0.67001.17180.86540.194*
C170.4680 (4)0.7897 (3)0.3524 (3)0.0567 (11)
H17A0.46490.82240.28250.068*
H17B0.38380.81450.39480.068*
C180.5044 (4)0.6589 (3)0.3698 (3)0.0572 (11)
H18A0.51620.62660.43750.069*
H18B0.43490.63450.36670.069*
C190.6511 (4)0.4846 (4)0.3333 (3)0.0811 (14)
H19A0.58350.45510.33540.122*
H19B0.66400.46490.39970.122*
H19C0.72710.45130.28770.122*
C200.5971 (4)0.6400 (4)0.1975 (3)0.0798 (14)
H20A0.52410.61670.20200.120*
H20B0.66970.60040.15320.120*
H20C0.58350.72210.17140.120*
C210.8560 (4)0.6183 (4)0.7304 (3)0.0565 (11)
C220.7540 (4)0.5639 (3)0.6306 (3)0.0529 (11)
C230.8405 (3)0.6098 (3)0.5360 (3)0.0464 (10)
C240.9353 (3)0.6535 (3)0.5412 (3)0.0468 (10)
C250.9461 (3)0.6572 (3)0.6348 (3)0.0524 (11)
C261.0414 (4)0.6991 (4)0.6382 (3)0.0631 (12)
H261.04810.70280.69980.076*
C271.1271 (4)0.7359 (4)0.5481 (4)0.0669 (13)
H271.19130.76310.55050.080*
C281.1178 (4)0.7325 (4)0.4568 (3)0.0646 (12)
H281.17610.75700.39810.078*
C291.0213 (3)0.6923 (3)0.4503 (3)0.0508 (10)
C301.0069 (4)0.6899 (3)0.3573 (3)0.0580 (11)
H301.06360.71500.29760.070*
C310.9108 (4)0.6512 (3)0.3526 (3)0.0520 (10)
C320.8288 (3)0.6093 (3)0.4460 (3)0.0513 (10)
H320.76510.58070.44470.062*
C330.9693 (4)0.6911 (4)0.1663 (3)0.0804 (15)
H33A1.05760.65330.16360.097*
H33B0.95760.77340.15760.097*
C340.9377 (6)0.6714 (5)0.0831 (4)0.119 (2)
H34A0.84940.70990.08610.142*
H34B0.94780.58910.09310.142*
C351.0166 (7)0.7137 (6)−0.0212 (4)0.157 (3)
H35A0.96360.7421−0.06800.188*
H35B1.04360.7785−0.01960.188*
C361.1246 (7)0.6296 (7)−0.0586 (6)0.207 (4)
H36A1.19440.6293−0.03670.310*
H36B1.14530.6476−0.13110.310*
H36C1.10750.5546−0.03340.310*
C370.6757 (4)0.5292 (3)0.8135 (3)0.0606 (12)
H37A0.70800.51700.87110.073*
H37B0.67160.45460.80960.073*
C380.5425 (4)0.6093 (4)0.8305 (3)0.0581 (11)
H38A0.51460.62910.76940.070*
H38B0.48580.56770.88400.070*
C390.4064 (4)0.7929 (4)0.8558 (3)0.0811 (15)
H39A0.38980.80270.79210.122*
H39B0.40330.86670.86480.122*
H39C0.34380.76040.90950.122*
C400.5512 (4)0.6922 (4)0.9577 (3)0.0810 (15)
H40A0.53680.76440.97540.121*
H40B0.63620.64760.95760.121*
H40C0.49300.64991.00620.121*
H20.649 (3)0.850 (3)0.763 (2)0.065 (14)*
H50.818 (3)0.645 (4)0.271 (3)0.082 (17)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.087 (2)0.081 (2)0.0454 (18)−0.0301 (18)−0.0225 (16)−0.0058 (15)
O20.0622 (18)0.076 (2)0.0559 (18)−0.0390 (17)−0.0017 (14)−0.0159 (15)
O30.075 (2)0.097 (3)0.059 (2)−0.0247 (19)−0.0253 (17)−0.0121 (17)
O40.0651 (19)0.080 (2)0.073 (2)−0.0406 (18)−0.0019 (15)−0.0221 (16)
N10.0513 (19)0.042 (2)0.054 (2)−0.0131 (16)−0.0176 (16)−0.0100 (16)
N20.070 (2)0.063 (3)0.052 (2)−0.032 (2)−0.0168 (19)−0.0054 (19)
N30.058 (2)0.054 (2)0.053 (2)−0.0076 (18)−0.0205 (17)−0.0165 (17)
N40.049 (2)0.050 (2)0.050 (2)−0.0138 (17)−0.0090 (16)−0.0056 (16)
N50.068 (3)0.079 (3)0.051 (2)−0.025 (2)−0.010 (2)−0.0106 (19)
N60.057 (2)0.050 (2)0.048 (2)−0.0141 (18)−0.0105 (16)−0.0056 (16)
C10.055 (2)0.042 (2)0.051 (3)−0.009 (2)−0.016 (2)−0.005 (2)
C20.048 (2)0.040 (2)0.054 (3)−0.012 (2)−0.011 (2)−0.0103 (19)
C30.040 (2)0.030 (2)0.045 (2)−0.0054 (17)−0.0114 (17)−0.0080 (17)
C40.040 (2)0.031 (2)0.047 (2)−0.0052 (17)−0.0103 (18)−0.0046 (17)
C50.047 (2)0.038 (2)0.048 (2)−0.0086 (19)−0.0135 (19)−0.0034 (18)
C60.057 (3)0.057 (3)0.044 (2)−0.015 (2)−0.009 (2)−0.001 (2)
C70.051 (3)0.063 (3)0.063 (3)−0.025 (2)−0.006 (2)0.004 (2)
C80.052 (3)0.058 (3)0.061 (3)−0.022 (2)−0.013 (2)−0.003 (2)
C90.041 (2)0.037 (2)0.052 (2)−0.0097 (18)−0.0105 (19)−0.0048 (18)
C100.051 (2)0.045 (3)0.061 (3)−0.013 (2)−0.020 (2)−0.010 (2)
C110.048 (2)0.040 (2)0.047 (2)−0.0108 (19)−0.0140 (19)−0.0057 (18)
C120.043 (2)0.038 (2)0.051 (2)−0.0127 (19)−0.0055 (18)−0.0070 (18)
C130.080 (3)0.073 (3)0.061 (3)−0.033 (3)−0.026 (2)−0.008 (2)
C140.153 (5)0.167 (6)0.049 (3)−0.115 (5)−0.034 (3)0.005 (3)
C150.160 (6)0.143 (6)0.069 (4)−0.065 (5)−0.007 (4)−0.024 (4)
C160.165 (6)0.123 (6)0.108 (5)−0.057 (5)−0.010 (4)−0.044 (4)
C170.053 (2)0.061 (3)0.065 (3)−0.012 (2)−0.022 (2)−0.021 (2)
C180.062 (3)0.060 (3)0.060 (3)−0.024 (2)−0.018 (2)−0.016 (2)
C190.086 (3)0.062 (3)0.097 (4)−0.006 (3)−0.037 (3)−0.021 (3)
C200.091 (3)0.094 (4)0.065 (3)−0.016 (3)−0.031 (3)−0.029 (3)
C210.048 (2)0.051 (3)0.066 (3)−0.006 (2)−0.020 (2)−0.007 (2)
C220.045 (2)0.047 (3)0.064 (3)−0.012 (2)−0.008 (2)−0.014 (2)
C230.041 (2)0.039 (2)0.054 (3)−0.0058 (19)−0.0110 (19)−0.0098 (19)
C240.039 (2)0.033 (2)0.061 (3)0.0009 (18)−0.016 (2)−0.0060 (19)
C250.043 (2)0.039 (2)0.070 (3)−0.004 (2)−0.020 (2)−0.005 (2)
C260.055 (3)0.057 (3)0.079 (3)−0.011 (2)−0.031 (2)−0.006 (2)
C270.048 (3)0.060 (3)0.090 (4)−0.018 (2)−0.022 (3)−0.004 (3)
C280.048 (3)0.057 (3)0.078 (3)−0.015 (2)−0.015 (2)0.001 (2)
C290.040 (2)0.038 (2)0.066 (3)−0.0065 (19)−0.013 (2)−0.004 (2)
C300.045 (2)0.049 (3)0.064 (3)−0.008 (2)−0.006 (2)−0.003 (2)
C310.050 (2)0.036 (2)0.060 (3)−0.006 (2)−0.012 (2)−0.004 (2)
C320.044 (2)0.043 (2)0.067 (3)−0.012 (2)−0.011 (2)−0.014 (2)
C330.080 (3)0.082 (4)0.062 (3)−0.021 (3)−0.005 (3)−0.006 (3)
C340.163 (6)0.124 (5)0.058 (3)−0.052 (5)−0.001 (4)−0.018 (3)
C350.190 (7)0.125 (6)0.086 (5)−0.025 (6)0.024 (5)−0.009 (4)
C360.196 (9)0.188 (9)0.203 (8)−0.089 (7)0.074 (7)−0.090 (7)
C370.063 (3)0.053 (3)0.057 (3)−0.019 (2)−0.010 (2)−0.001 (2)
C380.055 (3)0.063 (3)0.052 (3)−0.025 (2)−0.005 (2)−0.005 (2)
C390.064 (3)0.074 (4)0.080 (3)−0.011 (3)0.000 (3)−0.009 (3)
C400.103 (4)0.092 (4)0.048 (3)−0.034 (3)−0.016 (3)−0.009 (2)

Geometric parameters (Å, °)

O1—C11.216 (4)C17—C181.515 (5)
O2—C21.222 (4)C17—H17A0.9700
O3—C211.209 (4)C17—H17B0.9700
O4—C221.218 (4)C18—H18A0.9700
N1—C21.406 (4)C18—H18B0.9700
N1—C11.406 (4)C19—H19A0.9600
N1—C171.469 (4)C19—H19B0.9600
N2—C111.375 (4)C19—H19C0.9600
N2—C131.442 (5)C20—H20A0.9600
N2—H20.86 (2)C20—H20B0.9600
N3—C181.455 (5)C20—H20C0.9600
N3—C201.466 (4)C21—C251.481 (5)
N3—C191.466 (5)C22—C231.478 (5)
N4—C221.391 (5)C23—C321.347 (5)
N4—C211.404 (5)C23—C241.411 (5)
N4—C371.475 (4)C24—C251.407 (5)
N5—C311.372 (5)C24—C291.417 (5)
N5—C331.443 (5)C25—C261.391 (5)
N5—H50.85 (2)C26—C271.400 (5)
N6—C381.444 (5)C26—H260.9300
N6—C401.463 (4)C27—C281.366 (5)
N6—C391.468 (5)C27—H270.9300
C1—C51.480 (5)C28—C291.409 (5)
C2—C31.473 (5)C28—H280.9300
C3—C121.351 (4)C29—C301.410 (5)
C3—C41.412 (4)C30—C311.382 (5)
C4—C51.401 (5)C30—H300.9300
C4—C91.415 (5)C31—C321.426 (5)
C5—C61.380 (5)C32—H320.9300
C6—C71.400 (5)C33—C341.467 (6)
C6—H60.9300C33—H33A0.9700
C7—C81.365 (5)C33—H33B0.9700
C7—H70.9300C34—C351.514 (7)
C8—C91.408 (5)C34—H34A0.9700
C8—H80.9300C34—H34B0.9700
C9—C101.416 (5)C35—C361.413 (8)
C10—C111.375 (5)C35—H35A0.9700
C10—H100.9300C35—H35B0.9700
C11—C121.419 (5)C36—H36A0.9600
C12—H120.9300C36—H36B0.9600
C13—C141.550 (6)C36—H36C0.9600
C13—H13A0.9700C37—C381.527 (5)
C13—H13B0.9700C37—H37A0.9700
C14—C151.453 (7)C37—H37B0.9700
C14—H14A0.9700C38—H38A0.9700
C14—H14B0.9700C38—H38B0.9700
C15—C161.476 (7)C39—H39A0.9600
C15—H15A0.9700C39—H39B0.9600
C15—H15B0.9700C39—H39C0.9600
C16—H16A0.9600C40—H40A0.9600
C16—H16B0.9600C40—H40B0.9600
C16—H16C0.9600C40—H40C0.9600
C2—N1—C1124.9 (3)N3—C19—H19C109.5
C2—N1—C17116.3 (3)H19A—C19—H19C109.5
C1—N1—C17118.7 (3)H19B—C19—H19C109.5
C11—N2—C13124.1 (3)N3—C20—H20A109.5
C11—N2—H2113 (3)N3—C20—H20B109.5
C13—N2—H2118 (3)H20A—C20—H20B109.5
C18—N3—C20110.6 (3)N3—C20—H20C109.5
C18—N3—C19108.1 (3)H20A—C20—H20C109.5
C20—N3—C19109.0 (3)H20B—C20—H20C109.5
C22—N4—C21125.5 (3)O3—C21—N4120.5 (4)
C22—N4—C37115.9 (3)O3—C21—C25123.8 (4)
C21—N4—C37118.4 (3)N4—C21—C25115.7 (4)
C31—N5—C33122.4 (4)O4—C22—N4120.6 (4)
C31—N5—H5113 (3)O4—C22—C23122.0 (4)
C33—N5—H5120 (3)N4—C22—C23117.4 (4)
C38—N6—C40111.6 (3)C32—C23—C24120.6 (3)
C38—N6—C39109.5 (3)C32—C23—C22120.1 (4)
C40—N6—C39108.7 (3)C24—C23—C22119.3 (4)
O1—C1—N1120.0 (4)C25—C24—C23121.0 (3)
O1—C1—C5123.7 (4)C25—C24—C29120.2 (4)
N1—C1—C5116.3 (4)C23—C24—C29118.8 (4)
O2—C2—N1120.0 (4)C26—C25—C24120.0 (4)
O2—C2—C3123.2 (4)C26—C25—C21119.2 (4)
N1—C2—C3116.9 (3)C24—C25—C21120.8 (4)
C12—C3—C4120.1 (3)C25—C26—C27119.5 (4)
C12—C3—C2119.6 (3)C25—C26—H26120.3
C4—C3—C2120.3 (3)C27—C26—H26120.3
C5—C4—C3120.7 (3)C28—C27—C26121.1 (4)
C5—C4—C9120.5 (3)C28—C27—H27119.4
C3—C4—C9118.7 (3)C26—C27—H27119.4
C6—C5—C4120.3 (4)C27—C28—C29121.0 (4)
C6—C5—C1118.8 (4)C27—C28—H28119.5
C4—C5—C1120.9 (3)C29—C28—H28119.5
C5—C6—C7119.4 (4)C28—C29—C30122.7 (4)
C5—C6—H6120.3C28—C29—C24118.2 (4)
C7—C6—H6120.3C30—C29—C24119.1 (4)
C8—C7—C6120.7 (4)C31—C30—C29121.7 (4)
C8—C7—H7119.6C31—C30—H30119.1
C6—C7—H7119.6C29—C30—H30119.1
C7—C8—C9121.5 (4)N5—C31—C30123.8 (4)
C7—C8—H8119.2N5—C31—C32118.8 (4)
C9—C8—H8119.2C30—C31—C32117.4 (4)
C8—C9—C4117.5 (4)C23—C32—C31122.3 (4)
C8—C9—C10123.0 (4)C23—C32—H32118.8
C4—C9—C10119.6 (3)C31—C32—H32118.8
C11—C10—C9121.1 (4)N5—C33—C34112.5 (4)
C11—C10—H10119.5N5—C33—H33A109.1
C9—C10—H10119.5C34—C33—H33A109.1
C10—C11—N2124.3 (4)N5—C33—H33B109.1
C10—C11—C12118.0 (4)C34—C33—H33B109.1
N2—C11—C12117.7 (3)H33A—C33—H33B107.8
C3—C12—C11122.6 (3)C33—C34—C35114.7 (5)
C3—C12—H12118.7C33—C34—H34A108.6
C11—C12—H12118.7C35—C34—H34A108.6
N2—C13—C14109.9 (3)C33—C34—H34B108.6
N2—C13—H13A109.7C35—C34—H34B108.6
C14—C13—H13A109.7H34A—C34—H34B107.6
N2—C13—H13B109.7C36—C35—C34114.9 (6)
C14—C13—H13B109.7C36—C35—H35A108.5
H13A—C13—H13B108.2C34—C35—H35A108.5
C15—C14—C13116.4 (4)C36—C35—H35B108.5
C15—C14—H14A108.2C34—C35—H35B108.5
C13—C14—H14A108.2H35A—C35—H35B107.5
C15—C14—H14B108.2C35—C36—H36A109.5
C13—C14—H14B108.2C35—C36—H36B109.5
H14A—C14—H14B107.3H36A—C36—H36B109.5
C14—C15—C16116.1 (5)C35—C36—H36C109.5
C14—C15—H15A108.3H36A—C36—H36C109.5
C16—C15—H15A108.3H36B—C36—H36C109.5
C14—C15—H15B108.3N4—C37—C38113.2 (3)
C16—C15—H15B108.3N4—C37—H37A108.9
H15A—C15—H15B107.4C38—C37—H37A108.9
C15—C16—H16A109.5N4—C37—H37B108.9
C15—C16—H16B109.5C38—C37—H37B108.9
H16A—C16—H16B109.5H37A—C37—H37B107.8
C15—C16—H16C109.5N6—C38—C37114.1 (3)
H16A—C16—H16C109.5N6—C38—H38A108.7
H16B—C16—H16C109.5C37—C38—H38A108.7
N1—C17—C18113.6 (3)N6—C38—H38B108.7
N1—C17—H17A108.9C37—C38—H38B108.7
C18—C17—H17A108.9H38A—C38—H38B107.6
N1—C17—H17B108.9N6—C39—H39A109.5
C18—C17—H17B108.9N6—C39—H39B109.5
H17A—C17—H17B107.7H39A—C39—H39B109.5
N3—C18—C17114.7 (3)N6—C39—H39C109.5
N3—C18—H18A108.6H39A—C39—H39C109.5
C17—C18—H18A108.6H39B—C39—H39C109.5
N3—C18—H18B108.6N6—C40—H40A109.5
C17—C18—H18B108.6N6—C40—H40B109.5
H18A—C18—H18B107.6H40A—C40—H40B109.5
N3—C19—H19A109.5N6—C40—H40C109.5
N3—C19—H19B109.5H40A—C40—H40C109.5
H19A—C19—H19B109.5H40B—C40—H40C109.5
C2—N1—C1—O1−175.7 (3)C22—N4—C21—O3−178.5 (4)
C17—N1—C1—O1−0.1 (5)C37—N4—C21—O3−2.9 (6)
C2—N1—C1—C54.2 (5)C22—N4—C21—C251.3 (5)
C17—N1—C1—C5179.8 (3)C37—N4—C21—C25177.0 (3)
C1—N1—C2—O2176.4 (3)C21—N4—C22—O4175.8 (4)
C17—N1—C2—O20.8 (5)C37—N4—C22—O40.1 (5)
C1—N1—C2—C3−4.5 (5)C21—N4—C22—C23−4.9 (5)
C17—N1—C2—C3179.8 (3)C37—N4—C22—C23179.4 (3)
O2—C2—C3—C121.6 (5)O4—C22—C23—C324.1 (6)
N1—C2—C3—C12−177.4 (3)N4—C22—C23—C32−175.2 (3)
O2—C2—C3—C4−178.8 (3)O4—C22—C23—C24−175.7 (4)
N1—C2—C3—C42.2 (5)N4—C22—C23—C245.0 (5)
C12—C3—C4—C5179.6 (3)C32—C23—C24—C25178.3 (3)
C2—C3—C4—C50.0 (5)C22—C23—C24—C25−1.9 (5)
C12—C3—C4—C9−0.2 (5)C32—C23—C24—C29−2.7 (5)
C2—C3—C4—C9−179.8 (3)C22—C23—C24—C29177.1 (3)
C3—C4—C5—C6−179.8 (3)C23—C24—C25—C26179.1 (3)
C9—C4—C5—C60.0 (5)C29—C24—C25—C260.1 (5)
C3—C4—C5—C1−0.3 (5)C23—C24—C25—C21−1.8 (5)
C9—C4—C5—C1179.5 (3)C29—C24—C25—C21179.2 (3)
O1—C1—C5—C6−2.2 (6)O3—C21—C25—C261.1 (6)
N1—C1—C5—C6177.9 (3)N4—C21—C25—C26−178.7 (3)
O1—C1—C5—C4178.3 (4)O3—C21—C25—C24−178.0 (4)
N1—C1—C5—C4−1.6 (5)N4—C21—C25—C242.1 (5)
C4—C5—C6—C7−0.1 (6)C24—C25—C26—C27−1.0 (6)
C1—C5—C6—C7−179.6 (3)C21—C25—C26—C27179.9 (4)
C5—C6—C7—C80.3 (6)C25—C26—C27—C280.8 (6)
C6—C7—C8—C9−0.4 (6)C26—C27—C28—C290.3 (6)
C7—C8—C9—C40.2 (6)C27—C28—C29—C30178.5 (4)
C7—C8—C9—C10−179.9 (4)C27—C28—C29—C24−1.1 (6)
C5—C4—C9—C8−0.1 (5)C25—C24—C29—C280.9 (5)
C3—C4—C9—C8179.8 (3)C23—C24—C29—C28−178.1 (3)
C5—C4—C9—C10−179.9 (3)C25—C24—C29—C30−178.8 (3)
C3—C4—C9—C10−0.1 (5)C23—C24—C29—C302.2 (5)
C8—C9—C10—C11−179.1 (4)C28—C29—C30—C31−179.4 (4)
C4—C9—C10—C110.7 (5)C24—C29—C30—C310.3 (6)
C9—C10—C11—N2−178.0 (3)C33—N5—C31—C30−3.5 (6)
C9—C10—C11—C12−1.1 (5)C33—N5—C31—C32178.4 (4)
C13—N2—C11—C10−3.9 (6)C29—C30—C31—N5179.6 (4)
C13—N2—C11—C12179.2 (4)C29—C30—C31—C32−2.3 (6)
C4—C3—C12—C11−0.2 (5)C24—C23—C32—C310.6 (6)
C2—C3—C12—C11179.4 (3)C22—C23—C32—C31−179.2 (3)
C10—C11—C12—C30.8 (5)N5—C31—C32—C23−179.9 (4)
N2—C11—C12—C3178.0 (3)C30—C31—C32—C231.9 (6)
C11—N2—C13—C14164.1 (4)C31—N5—C33—C34176.3 (4)
N2—C13—C14—C15−170.6 (5)N5—C33—C34—C35−179.2 (5)
C13—C14—C15—C1661.5 (8)C33—C34—C35—C3693.2 (8)
C2—N1—C17—C18−79.6 (4)C22—N4—C37—C38−77.6 (4)
C1—N1—C17—C18104.4 (4)C21—N4—C37—C38106.3 (4)
C20—N3—C18—C17−68.8 (4)C40—N6—C38—C37−68.5 (4)
C19—N3—C18—C17172.0 (3)C39—N6—C38—C37171.0 (3)
N1—C17—C18—N3−69.1 (4)N4—C37—C38—N6−70.1 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···N60.86 (2)2.33 (2)3.176 (5)173 (3)
N5—H5···N30.85 (2)2.37 (2)3.220 (5)172 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2282).

References

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