Bis[2,4-dibromo-6-(1-naphthyl­imino­meth­yl)phenolato-κ2N,O]bis­(N,N′-dimethyl­formamide-κO)cobalt(II)

Liu, Z.; Jin, L.X.; Xia, J.H.; Liu, E.X.; Li, G.Z.

doi:10.1107/S1600536807053044

Buy article online - an online subscription or single-article purchase is required to access this article.

Bis[2,4-dibromo-6-(1-naphthyliminomethyl)phenolato-κ²N,O]bis(N,N′-dimethylformamide-κO)cobalt(II)

Z. Liu, L. X. Jin, J. H. Xia, E. X. Liu and G. Z. Li

In the title compound, [Co(C₁₇H₁₀Br₂NO)₂(C₃H₇NO)₂], the cobalt(II) cation is coordinated by two N and two O atoms from two different Schiff base ligands, and two O atoms from dimethylformamide molecules, forming a slightly distorted octahedral geometry. In the crystal structure, C—H

Br hydrogen bonds link the molecules in rows.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053044/at2437sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053044/at2437Isup2.hkl Contains datablock I

CCDC reference: 672673

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.012 Å
R factor = 0.057
wR factor = 0.123
Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         41 Perc.
PLAT048_ALERT_1_C MoietyFormula Not Given ........................          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.93
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.64 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    -   O3      ..       7.65 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         12
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  Br3     ..       3.58 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  Br3    ..  C28     ..       3.34 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         28
            O4  -CO1 -O2  -C20   120.00  5.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         36
            O2  -CO1 -O4  -C38  -162.00  5.00   1.555   1.555   1.555   1.555
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........       C21A
                    C21A   H28B
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........       H28B
                    H28B   BR3A
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........       C21A
                    C21A   BR3A
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........       C21A
                    C21A   H28B   BR3A

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.934
            Tmax scaled      0.539 Tmin scaled      0.428
PLAT794_ALERT_5_G Check Predicted Bond Valency for Co1         (2)       2.01

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  17 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Schiff bases play an important role in inorganic chemistry as they easily form stable complexes with most transition metal ions (Mostafa & Haifaa, 2007, Musie et al., 2003; Patel et al., 2006). Schiff bases of isatin were reported to possess antibacterial, antifungal, antiviral, anti-HIV, antiprotozoal, and anthelmintic activities (Erçağ et al., 2006). We report herein the synthesis and crystal structure of the ternary mixed ligand complex resulting from the condensation of 1-naphthylamine-3,5-bibromo-2-hydroxy- benzaldehyde and Co(NO₃)₂.

As shown in Fig. 1, the Co^II cation lies on a twofold axis and is coordinated by two N and two O atoms from the Schiff base and two O atoms from N,N'-dimethyl-formamide, in a slightly distorted octahedral geometry. In the crystal weak, non-classical C—H···Br hydrogen bonds link the molecules in rows (Fig 2).

Related literature top

Schiff bases of isatin have been reported to possess antibacterial, antifungal, antiviral, anti-HIV, antiprotozoal, and anthelmintic activities (Erçağ et al., 2006).

For related literature, see: El-Behery & El-Twigry (2007); Mostafa & Haifaa (2007); Musie et al. (2003); Patel et al. (2006).

Experimental top

1-naphthylamine (0.286 g, 2 mmol) and 3,5-bibromo-2-hydroxy-benzaldehyde (0.560 g, 2 mmol) were mixed in ethanol and and stirred for 30 min at room temperature to yield the Schiff base 2,4-dibromo-6-((naphthalen-1-ylimino) methyl)phenol. A mixture of schiff base (0.201 g, 0.5 mmol), CoNO₃.6H₂O₂ (0.145 g, 0.5 mmol) and 6 drops of triethylamine in 5 ml e thanol and 5 ml DMF were sealed in a 30 ml Teflon-lined stainless steel vessel, which was heated at 333 K for 7 days under autogenous pressure. On cooling to room temperature blue crystals of the title compound were produced (yield: 53%, based on Co).

Computing details top

Data collection: SAINT (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top

	Fig. 1. A view of (I), showing 30% probability displacement ellipsoids.
	Fig. 2. Crystal packing of (I) with H-bonds drawn as dashed lines.

Bis[2,4-dibromo-6-(1-naphthyliminomethyl)phenolato-κ²N,O]βis(N,N'-dimethylformamide-κO)cobalt(II) top

Crystal data top

[Co(C₁₇H₁₀Br₂NO)₂(C₃H₇NO)₂]	F(000) = 2004
M_r = 1013.28	D_x = 1.661 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3177 reflections
a = 12.2884 (15) Å	θ = 2.6–25.1°
b = 17.069 (2) Å	µ = 4.41 mm⁻¹
c = 19.373 (2) Å	T = 298 K
β = 94.310 (2)°	Block, red
V = 4052.0 (9) Å³	0.21 × 0.15 × 0.14 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	7147 independent reflections
Radiation source: fine-focus sealed tube	2955 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.458, T_max = 0.577	k = −20→12
20849 measured reflections	l = −23→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0363P)²] where P = (F_o² + 2F_c²)/3
7147 reflections	(Δ/σ)_max = 0.001
478 parameters	Δρ_max = 0.77 e Å⁻³
0 restraints	Δρ_min = −0.75 e Å⁻³

Crystal data top

[Co(C₁₇H₁₀Br₂NO)₂(C₃H₇NO)₂]	V = 4052.0 (9) Å³
M_r = 1013.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.2884 (15) Å	µ = 4.41 mm⁻¹
b = 17.069 (2) Å	T = 298 K
c = 19.373 (2) Å	0.21 × 0.15 × 0.14 mm
β = 94.310 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	7147 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2955 reflections with I > 2σ(I)
T_min = 0.458, T_max = 0.577	R_int = 0.090
20849 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.00	Δρ_max = 0.77 e Å⁻³
7147 reflections	Δρ_min = −0.75 e Å⁻³
478 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 > σ(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

	x	y	z	U_iso*/U_eq
Co1	0.13607 (7)	0.33654 (5)	0.33329 (5)	0.0563 (3)
Br1	0.12914 (7)	0.62067 (5)	0.30379 (5)	0.0931 (3)
Br2	0.56760 (7)	0.64339 (5)	0.40923 (5)	0.0964 (3)
Br3	0.46208 (6)	0.31966 (5)	0.21106 (5)	0.0806 (3)
Br4	0.22348 (9)	0.36243 (7)	−0.04636 (5)	0.1212 (4)
N1	0.2821 (5)	0.3226 (4)	0.4022 (3)	0.0672 (17)
N2	0.0105 (5)	0.3460 (3)	0.2508 (4)	0.0591 (17)
N3	0.1000 (8)	0.0902 (6)	0.3565 (5)	0.108 (3)
N4	−0.1103 (6)	0.4246 (5)	0.4558 (4)	0.087 (2)
O1	0.1647 (4)	0.4516 (3)	0.3353 (2)	0.0640 (14)
O2	0.2388 (4)	0.3126 (3)	0.2614 (3)	0.0689 (14)
O3	0.0870 (4)	0.2193 (4)	0.3495 (3)	0.0841 (19)
O4	0.0254 (4)	0.3574 (3)	0.4115 (3)	0.0717 (15)
C1	0.3594 (6)	0.3749 (5)	0.4061 (4)	0.069 (2)
H1	0.4280	0.3584	0.4238	0.082*
C2	0.3489 (6)	0.4563 (4)	0.3853 (4)	0.057 (2)
C3	0.2534 (7)	0.4887 (5)	0.3540 (4)	0.058 (2)
C4	0.2571 (6)	0.5715 (5)	0.3426 (4)	0.061 (2)
C5	0.3470 (7)	0.6164 (4)	0.3585 (4)	0.068 (2)
H5	0.3449	0.6701	0.3503	0.081*
C6	0.4417 (6)	0.5815 (5)	0.3871 (4)	0.067 (2)
C7	0.4430 (6)	0.5024 (5)	0.4012 (4)	0.065 (2)
H7	0.5061	0.4792	0.4214	0.078*
C8	0.3173 (7)	0.2432 (5)	0.4243 (5)	0.069 (2)
C9	0.3873 (7)	0.2006 (5)	0.3865 (4)	0.075 (2)
H9	0.4152	0.2230	0.3478	0.090*
C10	0.4171 (7)	0.1233 (6)	0.4058 (5)	0.089 (3)
H10	0.4647	0.0950	0.3802	0.107*
C11	0.3740 (7)	0.0896 (5)	0.4641 (5)	0.088 (3)
H11	0.3907	0.0383	0.4771	0.106*
C12	0.3050 (7)	0.1357 (5)	0.5022 (5)	0.072 (2)
C13	0.2740 (6)	0.2138 (5)	0.4797 (5)	0.071 (2)
C14	0.2018 (6)	0.2559 (5)	0.5222 (5)	0.070 (2)
H14	0.1790	0.3062	0.5095	0.084*
C15	0.1672 (7)	0.2232 (6)	0.5794 (5)	0.096 (3)
H15	0.1234	0.2527	0.6067	0.115*
C16	0.1938 (8)	0.1482 (7)	0.5996 (5)	0.101 (3)
H16	0.1651	0.1264	0.6383	0.121*
C17	0.2620 (8)	0.1063 (5)	0.5624 (5)	0.091 (3)
H17	0.2815	0.0561	0.5772	0.109*
C18	0.0265 (6)	0.3441 (4)	0.1871 (5)	0.066 (2)
H18	−0.0356	0.3466	0.1566	0.079*
C19	0.1304 (6)	0.3386 (4)	0.1554 (4)	0.058 (2)
C20	0.2307 (6)	0.3256 (4)	0.1960 (5)	0.060 (2)
C21	0.3282 (6)	0.3260 (4)	0.1587 (4)	0.062 (2)
C22	0.3232 (7)	0.3361 (4)	0.0892 (5)	0.070 (2)
H22	0.3875	0.3360	0.0668	0.084*
C23	0.2257 (8)	0.3464 (5)	0.0510 (4)	0.074 (2)
C24	0.1296 (7)	0.3470 (4)	0.0833 (5)	0.073 (2)
H24	0.0636	0.3531	0.0570	0.087*
C25	−0.1008 (6)	0.3546 (5)	0.2669 (4)	0.064 (2)
C26	−0.1549 (7)	0.2914 (5)	0.2908 (4)	0.079 (2)
H26	−0.1213	0.2426	0.2935	0.095*
C27	−0.2619 (7)	0.3004 (6)	0.3114 (4)	0.085 (3)
H27	−0.2983	0.2574	0.3280	0.101*
C28	−0.3117 (7)	0.3706 (6)	0.3071 (4)	0.081 (3)
H28	−0.3816	0.3756	0.3220	0.098*
C29	−0.2612 (7)	0.4356 (6)	0.2811 (4)	0.073 (2)
C30	−0.1536 (6)	0.4284 (5)	0.2599 (4)	0.065 (2)
C31	−0.1004 (6)	0.4969 (5)	0.2373 (4)	0.073 (2)
H31	−0.0288	0.4938	0.2250	0.088*
C32	−0.1526 (8)	0.5658 (5)	0.2338 (5)	0.096 (3)
H32	−0.1167	0.6104	0.2198	0.115*
C33	−0.2614 (9)	0.5709 (6)	0.2512 (5)	0.107 (3)
H33	−0.2979	0.6185	0.2455	0.129*
C34	−0.3144 (7)	0.5091 (6)	0.2759 (5)	0.092 (3)
H34	−0.3850	0.5147	0.2893	0.111*
C35	0.1276 (9)	0.1659 (7)	0.3330 (5)	0.103 (3)
H35	0.1821	0.1705	0.3025	0.124*
C36	0.1576 (10)	0.0288 (7)	0.3275 (6)	0.148 (4)
H36A	0.1727	−0.0113	0.3617	0.222*
H36B	0.2250	0.0485	0.3124	0.222*
H36C	0.1145	0.0073	0.2887	0.222*
C37	0.0319 (9)	0.0735 (7)	0.4061 (7)	0.147 (5)
H37A	0.0672	0.0381	0.4391	0.220*
H37B	−0.0333	0.0497	0.3853	0.220*
H37C	0.0134	0.1210	0.4291	0.220*
C38	−0.0267 (7)	0.4174 (5)	0.4162 (4)	0.076 (2)
H38	−0.0072	0.4607	0.3907	0.091*
C39	−0.1474 (8)	0.3588 (7)	0.4917 (5)	0.130 (4)
H39A	−0.1188	0.3118	0.4727	0.195*
H39B	−0.2257	0.3572	0.4870	0.195*
H39C	−0.1229	0.3627	0.5398	0.195*
C40	−0.1711 (7)	0.4979 (6)	0.4565 (5)	0.118 (4)
H40A	−0.1250	0.5404	0.4446	0.177*
H40B	−0.1951	0.5065	0.5019	0.177*
H40C	−0.2334	0.4951	0.4236	0.177*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0579 (6)	0.0443 (6)	0.0663 (7)	−0.0026 (5)	0.0021 (5)	0.0004 (5)
Br1	0.0924 (7)	0.0550 (6)	0.1277 (8)	0.0024 (5)	−0.0203 (6)	0.0118 (5)
Br2	0.0829 (6)	0.0771 (6)	0.1281 (9)	−0.0278 (5)	−0.0003 (6)	−0.0108 (6)
Br3	0.0589 (5)	0.0855 (7)	0.0980 (7)	−0.0019 (4)	0.0084 (5)	−0.0063 (5)
Br4	0.1367 (9)	0.1577 (10)	0.0710 (7)	0.0335 (8)	0.0197 (6)	−0.0053 (7)
N1	0.074 (5)	0.050 (4)	0.077 (5)	−0.002 (4)	0.004 (4)	0.005 (4)
N2	0.051 (4)	0.053 (4)	0.074 (5)	0.003 (3)	0.009 (4)	−0.001 (4)
N3	0.122 (8)	0.070 (7)	0.131 (9)	−0.004 (6)	−0.007 (6)	0.021 (6)
N4	0.082 (6)	0.097 (7)	0.082 (6)	0.006 (5)	0.012 (5)	−0.009 (5)
O1	0.063 (3)	0.049 (3)	0.079 (4)	−0.004 (3)	0.000 (3)	0.002 (3)
O2	0.061 (3)	0.076 (4)	0.070 (4)	0.010 (3)	0.004 (3)	−0.002 (3)
O3	0.079 (4)	0.063 (4)	0.108 (5)	0.014 (3)	−0.008 (3)	−0.011 (4)
O4	0.072 (4)	0.069 (4)	0.074 (4)	0.008 (3)	0.007 (3)	0.001 (3)
C1	0.067 (5)	0.061 (6)	0.076 (6)	0.001 (5)	−0.007 (4)	0.002 (5)
C2	0.062 (5)	0.047 (5)	0.060 (5)	−0.001 (4)	0.006 (4)	−0.003 (4)
C3	0.065 (6)	0.050 (5)	0.059 (5)	−0.004 (5)	0.010 (5)	−0.001 (4)
C4	0.064 (5)	0.054 (5)	0.065 (6)	−0.004 (4)	0.002 (4)	0.005 (4)
C5	0.077 (6)	0.050 (5)	0.076 (6)	−0.013 (5)	0.007 (5)	0.003 (4)
C6	0.072 (6)	0.057 (6)	0.072 (6)	−0.016 (4)	0.004 (5)	−0.010 (4)
C7	0.063 (5)	0.061 (6)	0.073 (6)	−0.001 (4)	0.005 (4)	−0.013 (4)
C8	0.070 (6)	0.065 (6)	0.072 (7)	−0.009 (5)	0.000 (5)	0.003 (5)
C9	0.079 (6)	0.067 (7)	0.080 (7)	0.006 (5)	0.014 (5)	0.000 (5)
C10	0.092 (7)	0.082 (8)	0.093 (8)	0.014 (6)	0.005 (6)	−0.014 (6)
C11	0.091 (7)	0.076 (7)	0.097 (8)	−0.010 (6)	−0.003 (6)	0.009 (6)
C12	0.072 (6)	0.070 (7)	0.073 (7)	−0.008 (5)	0.002 (5)	0.008 (6)
C13	0.070 (6)	0.071 (7)	0.071 (7)	−0.014 (5)	0.004 (5)	0.008 (5)
C14	0.074 (6)	0.064 (6)	0.072 (6)	0.000 (5)	0.005 (5)	0.014 (5)
C15	0.101 (7)	0.093 (8)	0.097 (9)	−0.004 (6)	0.023 (6)	0.011 (6)
C16	0.102 (8)	0.109 (9)	0.094 (8)	−0.001 (7)	0.020 (6)	0.023 (7)
C17	0.092 (7)	0.087 (7)	0.091 (8)	−0.007 (6)	−0.006 (6)	0.022 (6)
C18	0.062 (6)	0.052 (5)	0.083 (7)	0.007 (4)	−0.002 (5)	−0.005 (5)
C19	0.064 (6)	0.052 (5)	0.058 (6)	0.001 (4)	0.002 (5)	−0.005 (4)
C20	0.065 (6)	0.051 (5)	0.063 (6)	0.006 (4)	0.009 (5)	−0.004 (4)
C21	0.075 (6)	0.052 (5)	0.061 (6)	0.006 (4)	0.013 (5)	−0.008 (4)
C22	0.075 (6)	0.068 (6)	0.071 (7)	0.007 (5)	0.024 (5)	−0.011 (5)
C23	0.086 (6)	0.072 (6)	0.065 (6)	0.011 (5)	0.008 (6)	−0.009 (4)
C24	0.075 (6)	0.073 (6)	0.070 (7)	0.007 (5)	0.002 (5)	−0.007 (5)
C25	0.056 (5)	0.057 (6)	0.078 (6)	−0.001 (5)	−0.002 (4)	0.004 (4)
C26	0.061 (6)	0.071 (6)	0.106 (7)	−0.001 (5)	0.007 (5)	0.007 (5)
C27	0.067 (6)	0.086 (8)	0.101 (7)	−0.026 (5)	0.012 (5)	0.013 (6)
C28	0.065 (6)	0.091 (8)	0.089 (7)	−0.010 (6)	0.007 (5)	−0.002 (6)
C29	0.066 (6)	0.076 (7)	0.078 (6)	0.009 (5)	0.007 (5)	−0.002 (5)
C30	0.053 (5)	0.067 (6)	0.075 (6)	0.002 (5)	0.006 (4)	−0.001 (5)
C31	0.064 (5)	0.065 (6)	0.092 (7)	0.012 (5)	0.010 (5)	0.010 (5)
C32	0.085 (7)	0.073 (7)	0.132 (9)	0.016 (6)	0.019 (6)	0.017 (6)
C33	0.101 (8)	0.086 (8)	0.137 (9)	0.037 (7)	0.018 (7)	0.015 (7)
C34	0.077 (7)	0.093 (8)	0.110 (8)	0.018 (6)	0.022 (6)	0.003 (6)
C35	0.105 (8)	0.097 (10)	0.108 (9)	−0.002 (7)	0.002 (6)	−0.001 (8)
C36	0.178 (12)	0.112 (10)	0.155 (12)	−0.020 (9)	0.018 (9)	−0.004 (8)
C37	0.142 (11)	0.142 (11)	0.157 (13)	−0.002 (9)	0.018 (9)	−0.041 (9)
C38	0.072 (6)	0.079 (7)	0.078 (7)	0.004 (5)	0.010 (5)	−0.006 (5)
C39	0.132 (9)	0.144 (10)	0.120 (9)	−0.002 (8)	0.053 (7)	0.016 (8)
C40	0.106 (8)	0.136 (10)	0.113 (8)	0.035 (7)	0.006 (6)	−0.041 (7)

Geometric parameters (Å, º) top

Co1—O2	1.992 (5)	C15—C16	1.371 (11)
Co1—O1	1.996 (5)	C15—H15	0.9300
Co1—O3	2.120 (6)	C16—C17	1.350 (11)
Co1—O4	2.140 (5)	C16—H16	0.9300
Co1—N2	2.143 (6)	C17—H17	0.9300
Co1—N1	2.168 (6)	C18—C19	1.461 (10)
Br1—C4	1.887 (7)	C18—H18	0.9300
Br2—C6	1.896 (7)	C19—C24	1.405 (9)
Br3—C21	1.870 (8)	C19—C20	1.429 (10)
Br4—C23	1.904 (8)	C20—C21	1.444 (9)
N1—C1	1.301 (8)	C21—C22	1.354 (9)
N1—C8	1.474 (9)	C22—C23	1.371 (10)
N2—C18	1.264 (8)	C22—H22	0.9300
N2—C25	1.433 (8)	C23—C24	1.377 (10)
N3—C37	1.351 (11)	C24—H24	0.9300
N3—C36	1.405 (11)	C25—C26	1.365 (9)
N3—C35	1.420 (12)	C25—C30	1.419 (9)
N4—C38	1.333 (9)	C26—C27	1.411 (10)
N4—C39	1.415 (10)	C26—H26	0.9300
N4—C40	1.457 (10)	C27—C28	1.345 (10)
O1—C3	1.288 (8)	C27—H27	0.9300
O2—C20	1.282 (8)	C28—C29	1.384 (10)
O3—C35	1.098 (10)	C28—H28	0.9300
O4—C38	1.215 (8)	C29—C34	1.415 (11)
C1—C2	1.451 (9)	C29—C30	1.420 (9)
C1—H1	0.9300	C30—C31	1.425 (10)
C2—C3	1.394 (9)	C31—C32	1.338 (10)
C2—C7	1.413 (9)	C31—H31	0.9300
C3—C4	1.433 (9)	C32—C33	1.406 (11)
C4—C5	1.361 (9)	C32—H32	0.9300
C5—C6	1.386 (9)	C33—C34	1.346 (11)
C5—H5	0.9300	C33—H33	0.9300
C6—C7	1.377 (9)	C34—H34	0.9300
C7—H7	0.9300	C35—H35	0.9300
C8—C13	1.333 (10)	C36—H36A	0.9600
C8—C9	1.378 (10)	C36—H36B	0.9600
C9—C10	1.412 (10)	C36—H36C	0.9600
C9—H9	0.9300	C37—H37A	0.9600
C10—C11	1.407 (10)	C37—H37B	0.9600
C10—H10	0.9300	C37—H37C	0.9600
C11—C12	1.407 (10)	C38—H38	0.9300
C11—H11	0.9300	C39—H39A	0.9600
C12—C17	1.408 (11)	C39—H39B	0.9600
C12—C13	1.444 (11)	C39—H39C	0.9600
C13—C14	1.445 (10)	C40—H40A	0.9600
C14—C15	1.338 (10)	C40—H40B	0.9600
C14—H14	0.9300	C40—H40C	0.9600

O2—Co1—O1	95.51 (19)	N2—C18—C19	128.1 (8)
O2—Co1—O3	96.4 (2)	N2—C18—H18	116.0
O1—Co1—O3	167.9 (2)	C19—C18—H18	116.0
O2—Co1—O4	177.7 (2)	C24—C19—C20	120.4 (7)
O1—Co1—O4	86.7 (2)	C24—C19—C18	118.0 (8)
O3—Co1—O4	81.3 (2)	C20—C19—C18	121.6 (7)
O2—Co1—N2	87.3 (2)	O2—C20—C19	124.8 (7)
O1—Co1—N2	93.2 (2)	O2—C20—C21	119.3 (7)
O3—Co1—N2	89.1 (2)	C19—C20—C21	115.9 (7)
O4—Co1—N2	93.2 (2)	C22—C21—C20	121.4 (7)
O2—Co1—N1	82.5 (2)	C22—C21—Br3	121.2 (6)
O1—Co1—N1	87.7 (2)	C20—C21—Br3	117.2 (6)
O3—Co1—N1	92.1 (2)	C21—C22—C23	121.7 (7)
O4—Co1—N1	97.1 (2)	C21—C22—H22	119.1
N2—Co1—N1	169.8 (2)	C23—C22—H22	119.1
C1—N1—C8	114.6 (6)	C22—C23—C24	120.0 (8)
C1—N1—Co1	121.7 (5)	C22—C23—Br4	120.0 (7)
C8—N1—Co1	119.4 (5)	C24—C23—Br4	120.0 (7)
C18—N2—C25	115.9 (7)	C23—C24—C19	120.5 (8)
C18—N2—Co1	124.8 (5)	C23—C24—H24	119.7
C25—N2—Co1	119.4 (5)	C19—C24—H24	119.7
C37—N3—C36	119.0 (10)	C26—C25—C30	120.2 (7)
C37—N3—C35	126.5 (11)	C26—C25—N2	119.4 (7)
C36—N3—C35	114.3 (11)	C30—C25—N2	120.4 (7)
C38—N4—C39	120.0 (8)	C25—C26—C27	119.9 (8)
C38—N4—C40	120.2 (9)	C25—C26—H26	120.1
C39—N4—C40	119.5 (8)	C27—C26—H26	120.1
C3—O1—Co1	129.3 (5)	C28—C27—C26	120.6 (8)
C20—O2—Co1	130.5 (5)	C28—C27—H27	119.7
C35—O3—Co1	126.8 (8)	C26—C27—H27	119.7
C38—O4—Co1	124.0 (6)	C27—C28—C29	121.4 (8)
N1—C1—C2	126.4 (7)	C27—C28—H28	119.3
N1—C1—H1	116.8	C29—C28—H28	119.3
C2—C1—H1	116.8	C28—C29—C34	121.3 (9)
C3—C2—C7	121.6 (7)	C28—C29—C30	119.3 (8)
C3—C2—C1	123.7 (7)	C34—C29—C30	119.4 (9)
C7—C2—C1	114.7 (8)	C25—C30—C29	118.5 (8)
O1—C3—C2	126.5 (7)	C25—C30—C31	122.8 (7)
O1—C3—C4	118.5 (7)	C29—C30—C31	118.5 (8)
C2—C3—C4	115.0 (7)	C32—C31—C30	120.5 (8)
C5—C4—C3	123.7 (7)	C32—C31—H31	119.7
C5—C4—Br1	118.6 (6)	C30—C31—H31	119.7
C3—C4—Br1	117.7 (6)	C31—C32—C33	120.2 (9)
C4—C5—C6	119.4 (7)	C31—C32—H32	119.9
C4—C5—H5	120.3	C33—C32—H32	119.9
C6—C5—H5	120.3	C34—C33—C32	122.0 (9)
C7—C6—C5	119.9 (7)	C34—C33—H33	119.0
C7—C6—Br2	120.3 (7)	C32—C33—H33	119.0
C5—C6—Br2	119.8 (6)	C33—C34—C29	119.2 (9)
C6—C7—C2	120.3 (7)	C33—C34—H34	120.4
C6—C7—H7	119.9	C29—C34—H34	120.4
C2—C7—H7	119.9	O3—C35—N3	122.5 (12)
C13—C8—C9	122.1 (9)	O3—C35—H35	118.7
C13—C8—N1	116.9 (8)	N3—C35—H35	118.7
C9—C8—N1	120.8 (8)	N3—C36—H36A	109.5
C8—C9—C10	120.8 (8)	N3—C36—H36B	109.5
C8—C9—H9	119.6	H36A—C36—H36B	109.5
C10—C9—H9	119.6	N3—C36—H36C	109.5
C11—C10—C9	119.3 (8)	H36A—C36—H36C	109.5
C11—C10—H10	120.4	H36B—C36—H36C	109.5
C9—C10—H10	120.4	N3—C37—H37A	109.5
C12—C11—C10	118.1 (9)	N3—C37—H37B	109.5
C12—C11—H11	121.0	H37A—C37—H37B	109.5
C10—C11—H11	121.0	N3—C37—H37C	109.5
C11—C12—C17	120.9 (9)	H37A—C37—H37C	109.5
C11—C12—C13	120.9 (9)	H37B—C37—H37C	109.5
C17—C12—C13	118.2 (9)	O4—C38—N4	123.7 (9)
C8—C13—C12	118.6 (9)	O4—C38—H38	118.2
C8—C13—C14	124.8 (9)	N4—C38—H38	118.2
C12—C13—C14	116.5 (8)	N4—C39—H39A	109.5
C15—C14—C13	120.7 (8)	N4—C39—H39B	109.5
C15—C14—H14	119.6	H39A—C39—H39B	109.5
C13—C14—H14	119.6	N4—C39—H39C	109.5
C14—C15—C16	122.8 (9)	H39A—C39—H39C	109.5
C14—C15—H15	118.6	H39B—C39—H39C	109.5
C16—C15—H15	118.6	N4—C40—H40A	109.5
C17—C16—C15	119.1 (10)	N4—C40—H40B	109.5
C17—C16—H16	120.4	H40A—C40—H40B	109.5
C15—C16—H16	120.4	N4—C40—H40C	109.5
C16—C17—C12	122.6 (9)	H40A—C40—H40C	109.5
C16—C17—H17	118.7	H40B—C40—H40C	109.5
C12—C17—H17	118.7

O2—Co1—N1—C1	72.8 (6)	C10—C11—C12—C17	−177.9 (7)
O1—Co1—N1—C1	−23.0 (6)	C10—C11—C12—C13	3.6 (12)
O3—Co1—N1—C1	169.1 (6)	C9—C8—C13—C12	2.4 (12)
O4—Co1—N1—C1	−109.4 (6)	N1—C8—C13—C12	178.9 (6)
N2—Co1—N1—C1	72.4 (15)	C9—C8—C13—C14	178.9 (7)
O2—Co1—N1—C8	−82.7 (6)	N1—C8—C13—C14	−4.6 (11)
O1—Co1—N1—C8	−178.5 (6)	C11—C12—C13—C8	−3.9 (11)
O3—Co1—N1—C8	13.6 (6)	C17—C12—C13—C8	177.6 (7)
O4—Co1—N1—C8	95.1 (6)	C11—C12—C13—C14	179.3 (7)
N2—Co1—N1—C8	−83.1 (14)	C17—C12—C13—C14	0.8 (10)
O2—Co1—N2—C18	−7.3 (6)	C8—C13—C14—C15	−176.0 (8)
O1—Co1—N2—C18	88.1 (6)	C12—C13—C14—C15	0.6 (11)
O3—Co1—N2—C18	−103.8 (6)	C13—C14—C15—C16	−2.8 (14)
O4—Co1—N2—C18	174.9 (6)	C14—C15—C16—C17	3.5 (15)
N1—Co1—N2—C18	−6.9 (17)	C15—C16—C17—C12	−2.0 (14)
O2—Co1—N2—C25	172.2 (5)	C11—C12—C17—C16	−178.6 (9)
O1—Co1—N2—C25	−92.5 (5)	C13—C12—C17—C16	−0.1 (12)
O3—Co1—N2—C25	75.7 (5)	C25—N2—C18—C19	177.8 (7)
O4—Co1—N2—C25	−5.6 (5)	Co1—N2—C18—C19	−2.7 (11)
N1—Co1—N2—C25	172.6 (12)	N2—C18—C19—C24	−172.4 (7)
O2—Co1—O1—C3	−64.5 (6)	N2—C18—C19—C20	7.2 (11)
O3—Co1—O1—C3	106.9 (11)	Co1—O2—C20—C19	−21.0 (10)
O4—Co1—O1—C3	114.9 (6)	Co1—O2—C20—C21	160.2 (5)
N2—Co1—O1—C3	−152.1 (6)	C24—C19—C20—O2	−175.6 (7)
N1—Co1—O1—C3	17.7 (6)	C18—C19—C20—O2	4.8 (11)
O1—Co1—O2—C20	−73.7 (6)	C24—C19—C20—C21	3.1 (9)
O3—Co1—O2—C20	108.1 (6)	C18—C19—C20—C21	−176.5 (6)
O4—Co1—O2—C20	120 (5)	O2—C20—C21—C22	177.1 (7)
N2—Co1—O2—C20	19.3 (6)	C19—C20—C21—C22	−1.7 (10)
N1—Co1—O2—C20	−160.6 (6)	O2—C20—C21—Br3	−7.4 (9)
O2—Co1—O3—C35	15.3 (9)	C19—C20—C21—Br3	173.7 (5)
O1—Co1—O3—C35	−156.1 (10)	C20—C21—C22—C23	0.0 (11)
O4—Co1—O3—C35	−164.2 (9)	Br3—C21—C22—C23	−175.2 (6)
N2—Co1—O3—C35	102.4 (9)	C21—C22—C23—C24	0.2 (12)
N1—Co1—O3—C35	−67.4 (9)	C21—C22—C23—Br4	178.8 (6)
O2—Co1—O4—C38	−162 (5)	C22—C23—C24—C19	1.2 (12)
O1—Co1—O4—C38	31.4 (6)	Br4—C23—C24—C19	−177.3 (5)
O3—Co1—O4—C38	−150.3 (6)	C20—C19—C24—C23	−3.0 (11)
N2—Co1—O4—C38	−61.7 (6)	C18—C19—C24—C23	176.6 (7)
N1—Co1—O4—C38	118.7 (6)	C18—N2—C25—C26	105.7 (8)
C8—N1—C1—C2	177.4 (7)	Co1—N2—C25—C26	−73.8 (8)
Co1—N1—C1—C2	20.8 (10)	C18—N2—C25—C30	−76.0 (9)
N1—C1—C2—C3	−4.1 (12)	Co1—N2—C25—C30	104.5 (7)
N1—C1—C2—C7	174.1 (7)	C30—C25—C26—C27	−2.7 (12)
Co1—O1—C3—C2	−8.2 (11)	N2—C25—C26—C27	175.6 (7)
Co1—O1—C3—C4	172.3 (5)	C25—C26—C27—C28	0.5 (13)
C7—C2—C3—O1	177.6 (6)	C26—C27—C28—C29	1.5 (13)
C1—C2—C3—O1	−4.4 (12)	C27—C28—C29—C34	179.2 (8)
C7—C2—C3—C4	−2.8 (10)	C27—C28—C29—C30	−1.4 (12)
C1—C2—C3—C4	175.2 (6)	C26—C25—C30—C29	2.8 (11)
O1—C3—C4—C5	−178.3 (7)	N2—C25—C30—C29	−175.5 (7)
C2—C3—C4—C5	2.1 (10)	C26—C25—C30—C31	177.9 (7)
O1—C3—C4—Br1	2.1 (9)	N2—C25—C30—C31	−0.4 (12)
C2—C3—C4—Br1	−177.5 (5)	C28—C29—C30—C25	−0.7 (11)
C3—C4—C5—C6	0.3 (11)	C34—C29—C30—C25	178.7 (7)
Br1—C4—C5—C6	179.9 (5)	C28—C29—C30—C31	−176.1 (7)
C4—C5—C6—C7	−2.2 (11)	C34—C29—C30—C31	3.3 (12)
C4—C5—C6—Br2	179.8 (5)	C25—C30—C31—C32	−177.7 (8)
C5—C6—C7—C2	1.4 (11)	C29—C30—C31—C32	−2.5 (12)
Br2—C6—C7—C2	179.5 (5)	C30—C31—C32—C33	−1.2 (14)
C3—C2—C7—C6	1.2 (11)	C31—C32—C33—C34	4.3 (15)
C1—C2—C7—C6	−177.0 (7)	C32—C33—C34—C29	−3.4 (15)
C1—N1—C8—C13	116.2 (8)	C28—C29—C34—C33	179.0 (9)
Co1—N1—C8—C13	−86.6 (8)	C30—C29—C34—C33	−0.4 (13)
C1—N1—C8—C9	−67.2 (9)	Co1—O3—C35—N3	168.7 (6)
Co1—N1—C8—C9	90.0 (8)	C37—N3—C35—O3	−7.6 (17)
C13—C8—C9—C10	−0.7 (12)	C36—N3—C35—O3	177.5 (11)
N1—C8—C9—C10	−177.1 (7)	Co1—O4—C38—N4	166.4 (6)
C8—C9—C10—C11	0.4 (12)	C39—N4—C38—O4	−4.2 (13)
C9—C10—C11—C12	−1.9 (12)	C40—N4—C38—O4	−177.7 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21a—H28b···Br3a	0.93	2.93	1.870	152

Experimental details

Crystal data
Chemical formula	[Co(C₁₇H₁₀Br₂NO)₂(C₃H₇NO)₂]
M_r	1013.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	12.2884 (15), 17.069 (2), 19.373 (2)
β (°)	94.310 (2)
V (Å³)	4052.0 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.41
Crystal size (mm)	0.21 × 0.15 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.458, 0.577
No. of measured, independent and observed [I > 2σ(I)] reflections	20849, 7147, 2955
R_int	0.090
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.123, 1.00
No. of reflections	7147
No. of parameters	478
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.75

Computer programs: SAINT (Bruker, 2001), SMART (Bruker, 2001), SHELXTL (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21a—H28b···Br3a	0.930	2.932	1.870	151.6

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page