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Acta Cryst. (2007). E63, m2274    [ doi:10.1107/S1600536807037579 ]

Bis{2,4-dibromo-6-[3-(cyclohexylamino)propyliminomethyl]phenolato}cobalt(III) perchlorate

K. Li, S.-S. Huang, Q. Zhou, H. Li and Y.-P. Diao

Abstract top

In the title compound, [Co(C16H21Br2N2O)2]ClO4, a centrosymmetric mononuclear Schiff base cobalt(III) complex, the Co atom is hexacoordinated by two O and four N atoms from two Schiff base ligands, forming an octahedral geometry.

Comment top

Cobalt complexes with Schiff base ligands have received much attention in recent years (Sacconi et al., 1965; Zakrzewski & Sacconi, 1968). Some of the complexes have been found to have pharmacological and antitumor properties (Hodnett et al., 1971; Hodnett & Dunn, 1972; Takeuchi et al., 1998). We have recently reported a few transition metal complexes (Diao, Huang et al., 2007; Diao, Shu et al., 2007; Diao, 2007a,b). As an extension of the work on the crystal structures of such complexes, we report herein the crystal structure of the title complex.

The complex is a centrosymmetric mononuclear Schiff base cobalt(III) complex, which consists of a cobalt(III) cation and a perchlorate anion. The Co atom is hexacoordinated by two O and four N atoms from two Schiff base ligands, forming an octahedral geometry (Fig. 1).

Related literature top

For related literature, see: Diao (2007a,b); Diao, Huang et al. (2007); Diao, Shu et al. (2007); Hodnett & Dunn (1972); Hodnett et al. (1971); Sacconi et al. (1965); Takeuchi et al. (1998); Zakrzewski & Sacconi (1968).

Experimental top

3,5-Dibromosalicylaldehyde (0.2 mmol, 56.0 mg), N-cyclohexyl-1,3-diaminopropane (0.2 mmol, 31.0 mg), and Cu(ClO4)·7H2O (0.1 mmol, 39.0 mg) were dissolved in a methanol solution (20 ml). The mixture was stirred for half an hour at room temperature, giving a brown solution. After allowing the solution to stand in air for a week, brown block-like crystals were formed.

Refinement top

H atoms were placed in calculated positions and constrained to ride on their parent atoms, with C—H = 0.93–0.97 Å, N—H = 0.91 Å, and with Uiso(H) set at 1.2Ueq(C,N). The ration of observed/unique reflections is low (38%), and the value of Rint is 0.14, due to the poor quality of the diffraction.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. Molecular structure of the complex with 30% probabily ellipsoids.
Bis{2,4-dibromo-6-[3-(cyclohexylamino)propyliminomethyl]phenolato}cobalt(III) perchlorate top
Crystal data top
[Co(C16H21Br2N2O)2]ClO4F000 = 1976
Mr = 992.72Dx = 1.781 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1447 reflections
a = 16.208 (3) Åθ = 2.3–24.5º
b = 12.801 (3) ŵ = 4.90 mm−1
c = 18.060 (4) ÅT = 298 (2) K
β = 98.91 (3)ºBlock, brown
V = 3701.8 (14) Å30.33 × 0.32 × 0.32 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		8354 independent reflections
Radiation source: fine-focus sealed tube3168 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.142
T = 298(2) Kθmax = 27.5º
ω scansθmin = 2.0º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −21→21
Tmin = 0.295, Tmax = 0.303k = −16→16
30784 measured reflectionsl = −22→23
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.075H-atom parameters constrained
wR(F2) = 0.213  w = 1/[σ2(Fo2) + (0.0821P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
8354 reflectionsΔρmax = 1.12 e Å−3
436 parametersΔρmin = −0.75 e Å−3
24 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Co(C16H21Br2N2O)2]ClO4V = 3701.8 (14) Å3
Mr = 992.72Z = 4
Monoclinic, P21/cMo Kα
a = 16.208 (3) ŵ = 4.90 mm−1
b = 12.801 (3) ÅT = 298 (2) K
c = 18.060 (4) Å0.33 × 0.32 × 0.32 mm
β = 98.91 (3)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		8354 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		3168 reflections with I > 2σ(I)
Tmin = 0.295, Tmax = 0.303Rint = 0.142
30784 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07524 restraints
wR(F2) = 0.213H-atom parameters constrained
S = 0.96Δρmax = 1.12 e Å−3
8354 reflectionsΔρmin = −0.75 e Å−3
436 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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) top
xyzUiso*/Ueq
Co10.50000.50000.50000.0388 (4)
Co20.00000.00000.50000.0351 (4)
Br10.15360 (8)0.79302 (11)0.28990 (8)0.0947 (5)
Br20.23554 (7)0.37506 (9)0.36766 (7)0.0779 (4)
Br30.40645 (7)0.02431 (11)0.36755 (8)0.0917 (5)
Br40.06878 (8)0.13017 (10)0.26659 (6)0.0795 (4)
Cl10.35696 (18)0.8654 (3)0.67797 (19)0.0731 (9)
O10.3871 (4)0.4778 (4)0.4574 (3)0.0465 (16)
O20.0500 (4)0.0608 (4)0.4218 (3)0.0443 (15)
O30.3804 (8)0.8974 (11)0.6126 (7)0.175 (5)
O40.2889 (8)0.9120 (11)0.6912 (7)0.174 (5)
O50.4137 (12)0.9087 (15)0.7300 (11)0.256 (8)
O60.3674 (9)0.7618 (13)0.6982 (9)0.206 (6)
N10.4761 (5)0.6429 (6)0.5224 (4)0.0442 (19)
N20.4722 (5)0.4576 (6)0.5999 (4)0.052 (2)
H2A0.52010.42650.62240.062*
N30.1045 (4)0.0001 (5)0.5661 (4)0.0374 (17)
N4−0.0236 (4)0.1438 (6)0.5369 (4)0.0453 (19)
H4A−0.07190.13220.55530.054*
C10.3510 (5)0.6588 (7)0.4321 (5)0.044 (2)
C20.3363 (6)0.5496 (8)0.4234 (5)0.046 (2)
C30.2619 (6)0.5196 (7)0.3778 (6)0.053 (3)
C40.2069 (6)0.5910 (9)0.3389 (5)0.059 (3)
H40.15740.56900.31010.071*
C50.2281 (7)0.6968 (9)0.3443 (6)0.064 (3)
C60.2971 (6)0.7307 (8)0.3913 (6)0.054 (3)
H60.30830.80190.39630.064*
C70.4161 (6)0.6962 (7)0.4881 (5)0.045 (2)
H70.41440.76660.50060.054*
C80.5282 (6)0.6920 (8)0.5894 (5)0.056 (3)
H8A0.50660.76100.59760.068*
H8B0.58510.70000.57980.068*
C90.5282 (8)0.6267 (9)0.6591 (6)0.078 (4)
H9A0.52090.67260.70030.094*
H9B0.58230.59330.67150.094*
C100.4603 (7)0.5423 (8)0.6518 (6)0.070 (3)
H10A0.45860.51250.70100.084*
H10B0.40660.57490.63520.084*
C110.4077 (6)0.3707 (7)0.5978 (5)0.046 (2)
H110.40150.34050.54740.055*
C120.4408 (7)0.2828 (8)0.6527 (6)0.071 (3)
H12A0.44810.30860.70380.085*
H12B0.49450.25850.64220.085*
C130.3771 (9)0.1920 (8)0.6434 (7)0.089 (4)
H13A0.37400.16240.59360.107*
H13B0.39580.13760.67950.107*
C140.2907 (10)0.2297 (12)0.6549 (8)0.114 (6)
H14A0.25150.17200.64750.136*
H14B0.29280.25490.70580.136*
C150.2627 (8)0.3127 (10)0.6025 (8)0.090 (4)
H15A0.20780.33560.61070.108*
H15B0.25750.28540.55190.108*
C160.3215 (6)0.4068 (8)0.6094 (7)0.076 (3)
H16A0.30070.45890.57210.091*
H16B0.32420.43820.65860.091*
C170.1947 (6)0.0204 (6)0.4686 (5)0.044 (2)
C180.1278 (6)0.0523 (7)0.4124 (5)0.045 (2)
C190.1514 (6)0.0796 (7)0.3438 (5)0.048 (2)
C200.2327 (8)0.0718 (8)0.3306 (6)0.070 (3)
H200.24600.09010.28400.084*
C210.2949 (6)0.0365 (8)0.3870 (7)0.060 (3)
C220.2758 (6)0.0135 (7)0.4557 (6)0.053 (3)
H220.3177−0.00700.49420.064*
C230.1772 (5)0.0054 (7)0.5443 (5)0.045 (2)
H230.2233−0.00120.58160.054*
C240.1034 (6)0.0094 (7)0.6471 (5)0.049 (2)
H24A0.16030.01450.67310.059*
H24B0.0785−0.05300.66470.059*
C250.0551 (7)0.1031 (8)0.6650 (5)0.061 (3)
H25A0.08810.13970.70640.073*
H25B0.00480.07880.68250.073*
C260.0299 (7)0.1804 (8)0.6032 (5)0.063 (3)
H26A0.00200.23810.62370.076*
H26B0.08050.20790.58790.076*
C27−0.0514 (5)0.2239 (6)0.4777 (5)0.040 (2)
H27−0.06800.18660.43030.048*
C28−0.1276 (6)0.2791 (8)0.4964 (6)0.063 (3)
H28A−0.11330.31750.54300.076*
H28B−0.17030.22830.50300.076*
C29−0.1616 (8)0.3557 (10)0.4322 (7)0.095 (4)
H29A−0.18180.31630.38710.113*
H29B−0.20810.39480.44600.113*
C30−0.0944 (10)0.4309 (10)0.4163 (8)0.105 (5)
H30A−0.11590.47360.37330.126*
H30B−0.07960.47680.45900.126*
C31−0.0177 (8)0.3742 (9)0.4010 (7)0.083 (4)
H31A0.02500.42450.39380.100*
H31B−0.03110.33380.35530.100*
C320.0156 (6)0.3016 (8)0.4656 (6)0.067 (3)
H32A0.06440.26480.45420.080*
H32B0.03200.34210.51090.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0420 (10)0.0357 (10)0.0374 (10)0.0002 (8)0.0021 (8)−0.0028 (8)
Co20.0375 (9)0.0342 (9)0.0329 (10)0.0023 (7)0.0031 (7)−0.0017 (8)
Br10.0855 (9)0.0993 (10)0.0913 (10)0.0441 (8)−0.0112 (8)0.0101 (8)
Br20.0671 (8)0.0720 (8)0.0864 (9)−0.0146 (6)−0.0138 (6)−0.0125 (7)
Br30.0655 (8)0.1031 (11)0.1179 (12)−0.0095 (7)0.0496 (8)−0.0105 (8)
Br40.0935 (9)0.0932 (9)0.0530 (7)0.0052 (7)0.0156 (6)0.0266 (7)
Cl10.0549 (18)0.088 (2)0.077 (2)0.0211 (16)0.0111 (16)0.0037 (18)
O10.053 (4)0.039 (4)0.046 (4)−0.002 (3)0.000 (3)0.000 (3)
O20.052 (4)0.046 (4)0.036 (4)0.000 (3)0.009 (3)0.005 (3)
O30.189 (8)0.200 (9)0.152 (8)0.061 (7)0.080 (7)0.013 (7)
O40.147 (7)0.231 (9)0.156 (8)0.089 (7)0.065 (6)0.045 (7)
O50.248 (11)0.246 (11)0.256 (11)−0.018 (9)−0.018 (9)−0.007 (9)
O60.214 (9)0.169 (9)0.239 (10)−0.003 (8)0.040 (8)0.021 (8)
N10.042 (5)0.041 (5)0.050 (5)0.002 (4)0.007 (4)−0.008 (4)
N20.067 (5)0.040 (5)0.048 (5)0.001 (4)0.008 (4)0.001 (4)
N30.042 (4)0.032 (4)0.035 (4)0.007 (3)−0.004 (3)−0.006 (3)
N40.048 (5)0.051 (5)0.034 (4)0.005 (4)−0.001 (4)−0.007 (4)
C10.041 (5)0.044 (6)0.047 (6)0.007 (5)0.010 (5)−0.001 (5)
C20.049 (6)0.050 (6)0.039 (6)−0.002 (5)0.008 (5)−0.004 (5)
C30.048 (6)0.051 (7)0.059 (7)−0.002 (5)0.001 (5)0.000 (5)
C40.046 (6)0.088 (9)0.043 (6)−0.002 (6)0.000 (5)−0.013 (6)
C50.062 (7)0.066 (8)0.062 (8)0.030 (6)0.006 (6)0.014 (6)
C60.056 (7)0.041 (6)0.065 (7)0.015 (5)0.016 (6)0.002 (5)
C70.044 (6)0.033 (5)0.060 (7)−0.001 (5)0.016 (5)−0.010 (5)
C80.062 (7)0.052 (7)0.052 (7)0.001 (5)−0.001 (5)−0.016 (5)
C90.105 (10)0.073 (8)0.054 (8)−0.006 (7)0.002 (7)−0.022 (6)
C100.095 (9)0.075 (8)0.045 (7)−0.012 (7)0.026 (6)−0.012 (6)
C110.055 (6)0.045 (6)0.036 (5)−0.005 (5)0.004 (4)0.014 (5)
C120.089 (8)0.054 (7)0.064 (7)−0.015 (6)−0.004 (6)0.011 (6)
C130.153 (13)0.038 (7)0.066 (8)−0.009 (8)−0.014 (9)0.010 (6)
C140.141 (14)0.101 (12)0.118 (12)−0.083 (11)0.078 (11)−0.030 (10)
C150.085 (9)0.072 (9)0.119 (12)−0.022 (7)0.036 (8)0.015 (9)
C160.052 (7)0.073 (8)0.107 (10)0.011 (6)0.026 (7)0.003 (7)
C170.056 (6)0.032 (5)0.043 (6)0.003 (4)0.006 (5)−0.003 (4)
C180.063 (7)0.028 (5)0.044 (6)−0.002 (5)0.007 (5)−0.006 (4)
C190.065 (7)0.050 (6)0.035 (6)−0.004 (5)0.019 (5)0.006 (5)
C200.091 (9)0.069 (8)0.064 (8)−0.012 (7)0.052 (7)−0.007 (6)
C210.046 (6)0.066 (7)0.071 (8)−0.011 (5)0.018 (6)−0.002 (6)
C220.049 (6)0.040 (6)0.072 (8)−0.008 (5)0.017 (5)−0.015 (5)
C230.031 (5)0.042 (6)0.058 (7)−0.007 (4)−0.005 (5)−0.002 (5)
C240.055 (6)0.053 (6)0.037 (6)0.010 (5)−0.003 (5)0.003 (5)
C250.081 (8)0.061 (7)0.036 (6)0.013 (6)−0.009 (5)−0.008 (5)
C260.082 (8)0.054 (7)0.048 (7)0.017 (6)−0.006 (6)−0.013 (5)
C270.051 (6)0.029 (5)0.041 (6)0.001 (4)0.006 (4)−0.007 (4)
C280.061 (7)0.067 (7)0.066 (7)0.007 (6)0.023 (6)−0.011 (6)
C290.103 (10)0.096 (11)0.084 (10)0.060 (9)0.012 (8)0.005 (8)
C300.143 (14)0.055 (9)0.112 (12)0.016 (9)0.003 (10)0.040 (8)
C310.100 (10)0.064 (8)0.082 (9)−0.022 (7)0.001 (8)0.022 (7)
C320.070 (8)0.065 (8)0.063 (7)−0.018 (6)0.006 (6)0.008 (6)
Geometric parameters (Å, °) top
Co1—O11.894 (6)C11—C121.541 (12)
Co1—O1i1.894 (6)C11—H110.9800
Co1—N11.926 (7)C12—C131.546 (14)
Co1—N1i1.926 (7)C12—H12A0.9700
Co1—N2i2.002 (7)C12—H12B0.9700
Co1—N22.002 (7)C13—C141.526 (17)
Co2—O2ii1.900 (6)C13—H13A0.9700
Co2—O21.900 (6)C13—H13B0.9700
Co2—N3ii1.915 (7)C14—C151.449 (18)
Co2—N31.915 (7)C14—H14A0.9700
Co2—N4ii2.014 (7)C14—H14B0.9700
Co2—N42.014 (7)C15—C161.529 (15)
Br1—C51.889 (9)C15—H15A0.9700
Br2—C31.901 (9)C15—H15B0.9700
Br3—C211.900 (10)C16—H16A0.9700
Br4—C191.891 (10)C16—H16B0.9700
Cl1—O41.309 (11)C17—C221.372 (12)
Cl1—O51.330 (18)C17—C181.425 (12)
Cl1—O31.359 (12)C17—C231.452 (13)
Cl1—O61.380 (15)C18—C191.397 (12)
O1—C21.319 (10)C19—C201.379 (13)
O2—C181.303 (10)C20—C211.394 (14)
N1—C71.268 (10)C20—H200.9300
N1—C81.503 (11)C21—C221.358 (14)
N2—C101.465 (12)C22—H220.9300
N2—C111.522 (11)C23—H230.9300
N2—H2A0.9100C24—C251.495 (12)
N3—C231.300 (10)C24—H24A0.9700
N3—C241.470 (11)C24—H24B0.9700
N4—C261.443 (11)C25—C261.500 (13)
N4—C271.500 (10)C25—H25A0.9700
N4—H4A0.9100C25—H25B0.9700
C1—C61.397 (12)C26—H26A0.9700
C1—C21.423 (12)C26—H26B0.9700
C1—C71.427 (12)C27—C281.507 (12)
C2—C31.405 (12)C27—C321.513 (12)
C3—C41.389 (13)C27—H270.9800
C4—C51.397 (14)C28—C291.553 (14)
C4—H40.9300C28—H28A0.9700
C5—C61.368 (13)C28—H28B0.9700
C6—H60.9300C29—C301.513 (17)
C7—H70.9300C29—H29A0.9700
C8—C91.510 (14)C29—H29B0.9700
C8—H8A0.9700C30—C311.501 (16)
C8—H8B0.9700C30—H30A0.9700
C9—C101.534 (14)C30—H30B0.9700
C9—H9A0.9700C31—C321.523 (14)
C9—H9B0.9700C31—H31A0.9700
C10—H10A0.9700C31—H31B0.9700
C10—H10B0.9700C32—H32A0.9700
C11—C161.518 (12)C32—H32B0.9700
O1—Co1—O1i180.00 (16)C13—C12—H12A110.0
O1—Co1—N190.8 (3)C11—C12—H12B110.0
O1i—Co1—N189.2 (3)C13—C12—H12B110.0
O1—Co1—N1i89.2 (3)H12A—C12—H12B108.4
O1i—Co1—N1i90.8 (3)C14—C13—C12111.0 (10)
N1—Co1—N1i180.000 (1)C14—C13—H13A109.4
O1—Co1—N2i90.7 (3)C12—C13—H13A109.4
O1i—Co1—N2i89.3 (3)C14—C13—H13B109.4
N1—Co1—N2i90.7 (3)C12—C13—H13B109.4
N1i—Co1—N2i89.3 (3)H13A—C13—H13B108.0
O1—Co1—N289.3 (3)C15—C14—C13110.1 (10)
O1i—Co1—N290.7 (3)C15—C14—H14A109.6
N1—Co1—N289.3 (3)C13—C14—H14A109.6
N1i—Co1—N290.7 (3)C15—C14—H14B109.6
N2i—Co1—N2180.000 (2)C13—C14—H14B109.6
O2ii—Co2—O2180.000 (1)H14A—C14—H14B108.2
O2ii—Co2—N3ii91.4 (3)C14—C15—C16113.4 (11)
O2—Co2—N3ii88.6 (3)C14—C15—H15A108.9
O2ii—Co2—N388.6 (3)C16—C15—H15A108.9
O2—Co2—N391.4 (3)C14—C15—H15B108.9
N3ii—Co2—N3180.000 (1)C16—C15—H15B108.9
O2ii—Co2—N4ii89.8 (3)H15A—C15—H15B107.7
O2—Co2—N4ii90.2 (3)C11—C16—C15108.9 (9)
N3ii—Co2—N4ii89.3 (3)C11—C16—H16A109.9
N3—Co2—N4ii90.7 (3)C15—C16—H16A109.9
O2ii—Co2—N490.2 (3)C11—C16—H16B109.9
O2—Co2—N489.8 (3)C15—C16—H16B109.9
N3ii—Co2—N490.7 (3)H16A—C16—H16B108.3
N3—Co2—N489.3 (3)C22—C17—C18122.8 (9)
N4ii—Co2—N4180.0 (4)C22—C17—C23118.9 (9)
O4—Cl1—O5101.0 (11)C18—C17—C23118.0 (8)
O4—Cl1—O3112.3 (8)O2—C18—C19119.9 (9)
O5—Cl1—O3103.5 (11)O2—C18—C17125.2 (8)
O4—Cl1—O6117.5 (9)C19—C18—C17114.9 (9)
O5—Cl1—O699.8 (10)C20—C19—C18122.4 (10)
O3—Cl1—O6118.8 (9)C20—C19—Br4118.9 (8)
C2—O1—Co1125.3 (6)C18—C19—Br4118.7 (8)
C18—O2—Co2126.5 (6)C19—C20—C21120.0 (9)
C7—N1—C8117.5 (8)C19—C20—H20120.0
C7—N1—Co1124.9 (6)C21—C20—H20120.0
C8—N1—Co1117.4 (6)C22—C21—C20119.8 (10)
C10—N2—C11113.5 (8)C22—C21—Br3120.6 (9)
C10—N2—Co1116.5 (6)C20—C21—Br3119.6 (9)
C11—N2—Co1115.1 (5)C21—C22—C17120.1 (10)
C10—N2—H2A103.1C21—C22—H22120.0
C11—N2—H2A103.1C17—C22—H22120.0
Co1—N2—H2A103.1N3—C23—C17127.7 (8)
C23—N3—C24116.7 (7)N3—C23—H23116.2
C23—N3—Co2124.5 (6)C17—C23—H23116.2
C24—N3—Co2118.3 (6)N3—C24—C25111.6 (7)
C26—N4—C27116.5 (7)N3—C24—H24A109.3
C26—N4—Co2116.8 (6)C25—C24—H24A109.3
C27—N4—Co2116.1 (5)N3—C24—H24B109.3
C26—N4—H4A101.0C25—C24—H24B109.3
C27—N4—H4A101.0H24A—C24—H24B108.0
Co2—N4—H4A101.0C24—C25—C26117.3 (8)
C6—C1—C2120.6 (9)C24—C25—H25A108.0
C6—C1—C7119.0 (9)C26—C25—H25A108.0
C2—C1—C7120.0 (8)C24—C25—H25B108.0
O1—C2—C3120.0 (8)C26—C25—H25B108.0
O1—C2—C1123.5 (8)H25A—C25—H25B107.2
C3—C2—C1116.5 (9)N4—C26—C25117.6 (8)
C4—C3—C2122.9 (9)N4—C26—H26A107.9
C4—C3—Br2118.3 (8)C25—C26—H26A107.9
C2—C3—Br2118.8 (7)N4—C26—H26B107.9
C3—C4—C5118.1 (9)C25—C26—H26B107.9
C3—C4—H4120.9H26A—C26—H26B107.2
C5—C4—H4120.9N4—C27—C28109.1 (7)
C6—C5—C4121.3 (9)N4—C27—C32114.1 (7)
C6—C5—Br1120.8 (9)C28—C27—C32110.8 (8)
C4—C5—Br1117.8 (8)N4—C27—H27107.5
C5—C6—C1120.2 (9)C28—C27—H27107.5
C5—C6—H6119.9C32—C27—H27107.5
C1—C6—H6119.9C27—C28—C29109.7 (8)
N1—C7—C1126.4 (8)C27—C28—H28A109.7
N1—C7—H7116.8C29—C28—H28A109.7
C1—C7—H7116.8C27—C28—H28B109.7
N1—C8—C9111.5 (8)C29—C28—H28B109.7
N1—C8—H8A109.3H28A—C28—H28B108.2
C9—C8—H8A109.3C30—C29—C28111.1 (10)
N1—C8—H8B109.3C30—C29—H29A109.4
C9—C8—H8B109.3C28—C29—H29A109.4
H8A—C8—H8B108.0C30—C29—H29B109.4
C8—C9—C10114.3 (9)C28—C29—H29B109.4
C8—C9—H9A108.7H29A—C29—H29B108.0
C10—C9—H9A108.7C31—C30—C29111.6 (10)
C8—C9—H9B108.7C31—C30—H30A109.3
C10—C9—H9B108.7C29—C30—H30A109.3
H9A—C9—H9B107.6C31—C30—H30B109.3
N2—C10—C9114.3 (9)C29—C30—H30B109.3
N2—C10—H10A108.7H30A—C30—H30B108.0
C9—C10—H10A108.7C30—C31—C32111.1 (10)
N2—C10—H10B108.7C30—C31—H31A109.4
C9—C10—H10B108.7C32—C31—H31A109.4
H10A—C10—H10B107.6C30—C31—H31B109.4
C16—C11—N2114.7 (8)C32—C31—H31B109.4
C16—C11—C12111.7 (8)H31A—C31—H31B108.0
N2—C11—C12110.4 (7)C27—C32—C31109.5 (8)
C16—C11—H11106.5C27—C32—H32A109.8
N2—C11—H11106.5C31—C32—H32A109.8
C12—C11—H11106.5C27—C32—H32B109.8
C11—C12—C13108.6 (8)C31—C32—H32B109.8
C11—C12—H12A110.0H32A—C32—H32B108.2
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y, −z+1.
Acknowledgements top

This project was financially supported by a research grant from Dalian Medical University.

references
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