Bis(5-bromo-1H-indole-3-carbaldehyde 2-nitro­benzoyl­hydrazonato-κ2N,O)bis­(N,N-dimethyl­formamide-κO)copper(II)

Ali, H.M.; Abdul Halim, S.N.; Ng, S.W.

doi:10.1107/S1600536806007616

Bis(5-bromo-1H-indole-3-carbaldehyde 2-nitrobenzoylhydrazonato-κ²N,O)bis(N,N-dimethylformamide-κO)copper(II)

H. M. Ali, S. N. Abdul Halim and S. W. Ng

The Cu atom in the title compound, [Cu(C₁₆H₁₀BrN₄O₃)₂(C₃H₇NO)₂], lies on a special position of $\overline{1}$ site symmetry in a grossly elongated CuN₂O₄ octahedral geometry [Cu

O_DMF = 3.014 (4) Å]. The Cu atom is also N,O-chelated by the hydrazonate ligand. An N—H

O hydrogen bond helps to consolidate the crystal packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007616/hb2016sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007616/hb2016Isup2.hkl Contains datablock I

CCDC reference: 605071

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.006 Å
R factor = 0.055
wR factor = 0.180
Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.114     0.686
            Tmin(prime) and Tmax expected:      0.201     0.686
            RR(prime) =      0.568
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.52
PLAT731_ALERT_1_B Bond    Calc     0.85(5), Rep   0.850(10) ......       5.00 su-Rat
              N4   -H4N     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.85(5), Rep   0.850(10) ......       5.00 su-Rat
              N4   -H4N     1.555   1.555

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.62 mm
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N5
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  O3      ..       3.36 Ang.
PLAT736_ALERT_1_C H...A   Calc     1.95(5), Rep     1.95(2) ......       2.50 su-Rat
              H4N  -O4      1.555   1.565

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: CrystalStructure (Rigaku/MSC, 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis(5-bromo-1H-indole-3-carbaldehyde 2-nitrobenzoylhydrazonato- κ²N,O)bis(N,N-dimethylformamide-κO)copper(II) top

Crystal data top

[Cu(C₁₆H₁₀BrN₄O₃)₂(C₃H₇NO)₂]	Z = 1
M_r = 982.11	F(000) = 495
Triclinic, P1	D_x = 1.573 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.643 (5) Å	Cell parameters from 3209 reflections
b = 9.102 (5) Å	θ = 2.4–28.0°
c = 14.302 (9) Å	µ = 2.52 mm⁻¹
α = 99.84 (2)°	T = 295 K
β = 99.27 (1)°	Block, green
γ = 106.43 (1)°	0.62 × 0.44 × 0.15 mm
V = 1037 (1) Å³

Data collection top

Rigaku Mercury CCD diffractometer	3797 independent reflections
Radiation source: medium-focus sealed tube	2915 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
Detector resolution: 13.65 pixels mm^-1	θ_max = 25.5°, θ_min = 2.4°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −10→11
T_min = 0.114, T_max = 0.686	l = −17→15
17658 measured reflections

Refinement top

Refinement on F²	Primary atom site location: Cu atom placed at 1/2, 1/2, 1/2
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.055	Hydrogen site location: difmap and geom
wR(F²) = 0.180	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.1064P)² + 0.1574P] where P = (F_o² + 2F_c²)/3
3797 reflections	(Δ/σ)_max = 0.001
274 parameters	Δρ_max = 0.78 e Å⁻³
1 restraint	Δρ_min = −0.64 e Å⁻³

Special details top

Experimental. A large crystal was used as the smaller ones did not diffract well; a 0.8 mm collimator was used on the diffractometer.

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

	x	y	z	U_iso*/U_eq
Br1	0.29765 (9)	1.06647 (7)	0.95543 (3)	0.0955 (3)
Cu1	0.5000	0.5000	0.5000	0.0468 (2)
O1	0.4860 (3)	0.5059 (3)	0.3647 (2)	0.054 (1)
O2	0.5973 (5)	0.3978 (5)	0.1791 (3)	0.096 (1)
O3	0.3561 (5)	0.2577 (4)	0.1874 (3)	0.087 (1)
O4	0.1452 (4)	0.2901 (4)	0.4329 (3)	0.083 (1)
N1	0.4541 (5)	0.3808 (5)	0.1808 (2)	0.065 (1)
N2	0.3812 (4)	0.7082 (3)	0.4090 (2)	0.046 (1)
N3	0.4216 (4)	0.6795 (3)	0.5011 (2)	0.044 (1)
N4	0.2160 (4)	1.0726 (4)	0.5329 (2)	0.053 (1)
N5	0.0272 (4)	0.3587 (5)	0.3019 (3)	0.074 (1)
C1	0.3896 (5)	0.5105 (5)	0.1646 (3)	0.053 (1)
C2	0.3428 (6)	0.5127 (7)	0.0685 (3)	0.072 (1)
C3	0.2820 (7)	0.6296 (7)	0.0465 (3)	0.084 (2)
C4	0.2684 (7)	0.7407 (6)	0.1209 (3)	0.078 (1)
C5	0.3137 (6)	0.7362 (5)	0.2170 (3)	0.062 (1)
C6	0.3764 (5)	0.6184 (4)	0.2419 (3)	0.046 (1)
C7	0.4193 (4)	0.6104 (4)	0.3454 (3)	0.045 (1)
C8	0.3941 (4)	0.7669 (4)	0.5735 (2)	0.043 (1)
C9	0.2773 (4)	0.9596 (4)	0.5002 (3)	0.048 (1)
C10	0.3261 (4)	0.8926 (4)	0.5750 (3)	0.044 (1)
C11	0.2921 (4)	0.9755 (4)	0.6603 (3)	0.044 (1)
C12	0.3158 (5)	0.9696 (4)	0.7588 (3)	0.053 (1)
C13	0.2653 (6)	1.0696 (5)	0.8204 (3)	0.063 (1)
C14	0.1935 (7)	1.1778 (6)	0.7900 (4)	0.079 (1)
C15	0.1717 (6)	1.1878 (5)	0.6955 (4)	0.070 (1)
C16	0.2227 (5)	1.0870 (4)	0.6306 (3)	0.051 (1)
C17	0.1028 (6)	0.2731 (6)	0.3438 (4)	0.073 (1)
C18	−0.0207 (8)	0.4752 (8)	0.3585 (6)	0.117 (2)
C19	−0.0172 (7)	0.334 (1)	0.1964 (5)	0.118 (3)
H4n	0.178 (6)	1.123 (6)	0.495 (3)	0.10 (2)*
H2	0.3521	0.4366	0.0194	0.086*
H3	0.2502	0.6340	−0.0180	0.101*
H4	0.2279	0.8202	0.1058	0.094*
H5	0.3025	0.8119	0.2657	0.075*
H8	0.4230	0.7445	0.6337	0.052*
H9	0.2860	0.9300	0.4363	0.058*
H12	0.3645	0.8998	0.7815	0.064*
H14	0.1605	1.2430	0.8345	0.094*
H15	0.1244	1.2596	0.6744	0.084*
H17	0.1262	0.1940	0.3038	0.087*
H18a	−0.0239	0.4543	0.4218	0.175*
H18b	−0.1283	0.4732	0.3270	0.175*
H18c	0.0578	0.5770	0.3649	0.175*
H19a	0.0277	0.2574	0.1668	0.177*
H19b	0.0269	0.4315	0.1780	0.177*
H19c	−0.1355	0.2970	0.1748	0.177*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1613 (7)	0.0884 (4)	0.0477 (4)	0.0516 (4)	0.0358 (3)	0.0125 (3)
Cu1	0.0722 (5)	0.0496 (4)	0.0300 (4)	0.0346 (3)	0.0124 (3)	0.0119 (3)
O1	0.081 (2)	0.061 (2)	0.033 (2)	0.043 (1)	0.013 (1)	0.013 (1)
O2	0.094 (3)	0.136 (3)	0.083 (3)	0.072 (3)	0.025 (2)	0.023 (2)
O3	0.125 (3)	0.070 (2)	0.070 (2)	0.040 (2)	0.017 (2)	0.014 (2)
O4	0.099 (2)	0.090 (2)	0.070 (2)	0.045 (2)	0.003 (2)	0.038 (2)
N1	0.088 (3)	0.080 (3)	0.033 (2)	0.044 (2)	0.011 (2)	0.004 (2)
N2	0.060 (2)	0.051 (2)	0.035 (2)	0.026 (1)	0.012 (1)	0.016 (1)
N3	0.061 (2)	0.044 (2)	0.036 (2)	0.027 (1)	0.013 (1)	0.013 (1)
N4	0.068 (2)	0.051 (2)	0.051 (2)	0.032 (2)	0.011 (2)	0.019 (2)
N5	0.060 (2)	0.076 (2)	0.085 (3)	0.017 (2)	−0.003 (2)	0.044 (2)
C1	0.060 (2)	0.067 (2)	0.038 (2)	0.028 (2)	0.012 (2)	0.016 (2)
C2	0.091 (3)	0.096 (3)	0.038 (2)	0.043 (3)	0.016 (2)	0.016 (2)
C3	0.111 (4)	0.118 (4)	0.040 (3)	0.057 (3)	0.015 (2)	0.032 (3)
C4	0.105 (4)	0.094 (3)	0.053 (3)	0.050 (3)	0.013 (2)	0.036 (3)
C5	0.081 (3)	0.070 (2)	0.049 (2)	0.036 (2)	0.015 (2)	0.026 (2)
C6	0.052 (2)	0.055 (2)	0.036 (2)	0.021 (2)	0.008 (2)	0.016 (2)
C7	0.052 (2)	0.046 (2)	0.039 (2)	0.017 (2)	0.008 (2)	0.014 (2)
C8	0.050 (2)	0.047 (2)	0.034 (2)	0.018 (2)	0.007 (1)	0.011 (2)
C9	0.056 (2)	0.051 (2)	0.042 (2)	0.024 (2)	0.009 (2)	0.015 (2)
C10	0.051 (2)	0.046 (2)	0.043 (2)	0.021 (2)	0.013 (2)	0.016 (2)
C11	0.052 (2)	0.041 (2)	0.043 (2)	0.020 (2)	0.011 (2)	0.010 (2)
C12	0.073 (3)	0.044 (2)	0.047 (2)	0.023 (2)	0.018 (2)	0.012 (2)
C13	0.087 (3)	0.060 (2)	0.047 (2)	0.030 (2)	0.021 (2)	0.011 (2)
C14	0.114 (4)	0.070 (3)	0.070 (3)	0.052 (3)	0.037 (3)	0.009 (2)
C15	0.098 (3)	0.062 (3)	0.072 (3)	0.052 (3)	0.027 (3)	0.018 (2)
C16	0.061 (2)	0.046 (2)	0.051 (2)	0.025 (2)	0.013 (2)	0.012 (2)
C17	0.072 (3)	0.068 (3)	0.078 (3)	0.025 (2)	0.008 (2)	0.024 (2)
C18	0.093 (4)	0.088 (4)	0.178 (7)	0.046 (4)	0.011 (4)	0.045 (4)
C19	0.078 (4)	0.170 (6)	0.092 (4)	0.004 (4)	−0.011 (3)	0.080 (5)

Geometric parameters (Å, º) top

C13—Br1	1.912 (5)	C8—C10	1.426 (5)
Cu1—O1	1.930 (3)	C9—C10	1.384 (5)
Cu1—O1ⁱ	1.930 (3)	C10—C11	1.438 (5)
Cu1—O4	3.014 (4)	C11—C12	1.403 (5)
Cu1—O4ⁱ	3.014 (4)	C11—C16	1.407 (5)
Cu1—N3	1.937 (3)	C12—C13	1.368 (6)
Cu1—N3ⁱ	1.937 (3)	C13—C14	1.396 (6)
O1—C7	1.289 (4)	C14—C15	1.356 (7)
O2—N1	1.208 (5)	C15—C16	1.403 (6)
O3—N1	1.227 (5)	N4—H4n	0.85 (1)
O4—C17	1.239 (6)	C2—H2	0.93
N1—C1	1.478 (5)	C3—H3	0.93
N2—C7	1.308 (5)	C4—H4	0.93
N2—N3	1.395 (4)	C5—H5	0.93
N3—C8	1.291 (5)	C8—H8	0.93
N4—C9	1.334 (5)	C9—H9	0.93
N4—C16	1.371 (5)	C12—H12	0.93
N5—C17	1.309 (5)	C14—H14	0.93
N5—C18	1.419 (8)	C15—H15	0.93
N5—C19	1.458 (7)	C17—H17	0.93
C1—C2	1.373 (6)	C18—H18a	0.96
C1—C6	1.390 (6)	C18—H18b	0.96
C2—C3	1.373 (7)	C18—H18c	0.96
C3—C4	1.381 (7)	C19—H19a	0.96
C4—C5	1.378 (6)	C19—H19b	0.96
C5—C6	1.403 (5)	C19—H19c	0.96
C6—C7	1.486 (5)

O1ⁱ—Cu1—O1	180	C12—C11—C10	134.9 (3)
O1—Cu1—O4	85.0 (1)	C16—C11—C10	106.6 (3)
O1—Cu1—N3	81.8 (1)	C13—C12—C11	118.1 (4)
O1—Cu1—N3ⁱ	98.2 (1)	C12—C13—C14	123.0 (4)
O1ⁱ—Cu1—N3	98.2 (1)	C12—C13—Br1	119.3 (3)
O1ⁱ—Cu1—N3ⁱ	81.8 (1)	C14—C13—Br1	117.7 (3)
O1ⁱ—Cu1—O4	95.0 (1)	C15—C14—C13	120.1 (4)
N3—Cu1—N3ⁱ	180	C14—C15—C16	118.2 (4)
N3—Cu1—O4	88.4 (1)	N4—C16—C15	130.3 (4)
N3ⁱ—Cu1—O4	91.7 (1)	N4—C16—C11	107.6 (3)
O1—Cu1—O4ⁱ	95.0 (1)	C15—C16—C11	122.1 (4)
O1ⁱ—Cu1—O4ⁱ	85.0 (1)	O4—C17—N5	124.5 (5)
N3—Cu1—O4ⁱ	91.7 (1)	C9—N4—H4n	122 (4)
N3ⁱ—Cu1—O4ⁱ	88.4 (1)	C16—N4—H4n	129 (4)
O4—Cu1—O4ⁱ	180	C3—C2—H2	120.7
C7—O1—Cu1	109.4 (2)	C1—C2—H2	120.7
C17—O4—Cu1	108.5 (3)	C2—C3—H3	120.2
O2—N1—O3	123.7 (4)	C4—C3—H3	120.2
O2—N1—C1	117.9 (4)	C5—C4—H4	119.3
O3—N1—C1	118.1 (4)	C3—C4—H4	119.3
C7—N2—N3	109.1 (3)	C4—C5—H5	119.7
C8—N3—N2	117.7 (3)	C6—C5—H5	119.7
C8—N3—Cu1	128.6 (2)	N3—C8—H8	115.2
N2—N3—Cu1	113.5 (2)	C10—C8—H8	115.2
C9—N4—C16	109.8 (3)	N4—C9—H9	124.8
C17—N5—C18	120.6 (5)	C10—C9—H9	124.8
C17—N5—C19	121.7 (5)	C13—C12—H12	121.0
C18—N5—C19	117.6 (5)	C11—C12—H12	121.0
C2—C1—C6	124.0 (4)	C15—C14—H14	120.0
C2—C1—N1	114.6 (4)	C13—C14—H14	120.0
C6—C1—N1	121.4 (3)	C14—C15—H15	120.9
C3—C2—C1	118.7 (5)	C16—C15—H15	120.9
C2—C3—C4	119.5 (4)	O4—C17—H17	117.8
C5—C4—C3	121.3 (4)	N5—C17—H17	117.8
C4—C5—C6	120.6 (4)	N5—C18—H18a	109.5
C1—C6—C5	115.9 (3)	N5—C18—H18b	109.5
C1—C6—C7	123.7 (3)	H18a—C18—H18b	109.5
C5—C6—C7	120.4 (4)	N5—C18—H18c	109.5
O1—C7—N2	125.7 (3)	H18a—C18—H18c	109.5
O1—C7—C6	117.8 (3)	H18b—C18—H18c	109.5
N2—C7—C6	116.6 (3)	N5—C19—H19a	109.5
N3—C8—C10	129.6 (3)	N5—C19—H19b	109.5
N4—C9—C10	110.4 (3)	H19a—C19—H19b	109.5
C9—C10—C8	130.0 (3)	N5—C19—H19c	109.5
C9—C10—C11	105.6 (3)	H19a—C19—H19c	109.5
C8—C10—C11	124.4 (3)	H19b—C19—H19c	109.5
C12—C11—C16	118.5 (3)

N3—Cu1—O1—C7	−6.2 (2)	C1—C6—C7—O1	6.3 (6)
N3ⁱ—Cu1—O1—C7	173.8 (2)	C5—C6—C7—O1	−175.8 (4)
O4—Cu1—O1—C7	82.8 (2)	C1—C6—C7—N2	−171.8 (4)
O1ⁱ—Cu1—O4—C17	−179.7 (3)	C5—C6—C7—N2	6.1 (5)
O1—Cu1—O4—C17	0.3 (3)	N2—N3—C8—C10	0.2 (6)
N3—Cu1—O4—C17	82.1 (3)	Cu1—N3—C8—C10	−175.3 (3)
N3ⁱ—Cu1—O4—C17	−97.9 (3)	C16—N4—C9—C10	0.6 (4)
C7—N2—N3—C8	179.2 (3)	N4—C9—C10—C8	178.4 (4)
C7—N2—N3—Cu1	−4.6 (3)	N4—C9—C10—C11	−0.7 (4)
O1ⁱ—Cu1—N3—C8	1.8 (3)	N3—C8—C10—C9	−3.0 (7)
O1—Cu1—N3—C8	−178.2 (3)	N3—C8—C10—C11	176.0 (4)
O4—Cu1—N3—C8	96.6 (3)	C9—C10—C11—C12	−177.8 (4)
O1ⁱ—Cu1—N3—N2	−173.9 (2)	C8—C10—C11—C12	3.0 (7)
O1—Cu1—N3—N2	6.1 (2)	C9—C10—C11—C16	0.6 (4)
O4—Cu1—N3—N2	−79.0 (2)	C8—C10—C11—C16	−178.6 (3)
O2—N1—C1—C2	82.3 (5)	C16—C11—C12—C13	2.0 (6)
O3—N1—C1—C2	−92.0 (5)	C10—C11—C12—C13	−179.7 (4)
O2—N1—C1—C6	−98.7 (5)	C11—C12—C13—C14	−0.8 (7)
O3—N1—C1—C6	87.0 (5)	C11—C12—C13—Br1	−179.4 (3)
C6—C1—C2—C3	1.3 (8)	C12—C13—C14—C15	−0.4 (8)
N1—C1—C2—C3	−179.7 (5)	Br1—C13—C14—C15	178.2 (4)
C1—C2—C3—C4	−0.4 (8)	C13—C14—C15—C16	0.2 (8)
C2—C3—C4—C5	−0.4 (9)	C9—N4—C16—C15	−179.4 (5)
C3—C4—C5—C6	0.5 (8)	C9—N4—C16—C11	−0.2 (4)
C2—C1—C6—C5	−1.2 (6)	C14—C15—C16—N4	−179.8 (5)
N1—C1—C6—C5	179.9 (4)	C14—C15—C16—C11	1.1 (7)
C2—C1—C6—C7	176.8 (4)	C12—C11—C16—N4	178.5 (3)
N1—C1—C6—C7	−2.1 (6)	C10—C11—C16—N4	−0.2 (4)
C4—C5—C6—C1	0.3 (6)	C12—C11—C16—C15	−2.3 (6)
C4—C5—C6—C7	−177.8 (4)	C10—C11—C16—C15	179.0 (4)
Cu1—O1—C7—N2	6.0 (5)	Cu1—O4—C17—N5	−94.4 (5)
Cu1—O1—C7—C6	−171.9 (3)	C18—N5—C17—O4	−3.7 (8)
N3—N2—C7—O1	−1.0 (5)	C19—N5—C17—O4	179.1 (5)
N3—N2—C7—C6	176.9 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4n···O4ⁱⁱ	0.85 (1)	1.95 (2)	2.777 (4)	163 (5)

Symmetry code: (ii) x, y+1, z.

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Bis(5-bromo-1H-indole-3-carbaldehyde 2-nitro­benzoyl­hydrazonato-κ2N,O)bis­(N,N-dimethyl­formamide-κO)copper(II)

Supporting information

Key indicators

checkCIF/PLATON results

Bis(5-bromo-1H-indole-3-carbaldehyde 2-nitrobenzoylhydrazonato-κ²N,O)bis(N,N-dimethylformamide-κO)copper(II)