Dibromo­{4-bromo-2-[(3-dimethyl­amino­propyl­imino)meth­yl]phenolato}zinc(II)

In the title mononuclear zinc(II) complex, [ZnBr₂(C₁₂H₁₇BrN₂O)], the Zn^II atom is four-coordinated by the imine N and phenolate O atoms of the Schiff base ligand, and by two Br atoms, forming a tetra­hedral geometry. In the crystal structure, the mol­ecules are linked through inter­molecular N—H...O hydrogen bonds and weak Br...Br inter­actions, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.015 Å
• R factor = 0.079
• wR factor = 0.268
• Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Br3    -   Zn1     ..      29.57 su

Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.268
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT084_ALERT_2_C High R2 Value ..................................       0.27
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.89 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.27 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Zn1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         15

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C12 H17 Br3 N2 O1 Zn1
            Atom count from _chemical_formula_moiety:

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   0 ALERT type 5 Informative message, check

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Computing details

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.

(I)

Crystal data

[ZnBr2(C12H17BrN2O)]	F(000) = 984
Mr = 510.38	Dx = 1.982 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1515 reflections
a = 7.037 (1) Å	θ = 2.4–24.5°
b = 15.039 (2) Å	µ = 8.44 mm^−1
c = 16.170 (2) Å	T = 298 K
β = 92.041 (3)°	Plate, colourless
V = 1710.2 (4) Å^3	0.20 × 0.08 × 0.06 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3518 independent reflections
Radiation source: fine-focus sealed tube	2069 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.072
ω scans	θmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.283, Tmax = 0.631	k = −18→18
13541 measured reflections	l = −20→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.268	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.1484P)^2 + 6.3675P] where P = (Fo^2 + 2Fc^2)/3
3518 reflections	(Δ/σ)max = 0.001
177 parameters	Δρmax = 1.07 e Å^−3
1 restraint	Δρmin = −2.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.25227 (18)	0.74403 (9)	0.61019 (8)	0.0416 (4)
Br1	0.9658 (2)	0.99421 (9)	0.84214 (9)	0.0584 (5)
Br2	0.0900 (2)	0.61025 (9)	0.58752 (9)	0.0596 (5)
Br3	0.1238 (3)	0.86920 (15)	0.53618 (15)	0.1067 (8)
O1	0.3096 (11)	0.7608 (6)	0.7276 (5)	0.049 (2)
N1	0.5271 (13)	0.7366 (6)	0.5799 (5)	0.037 (2)
N2	0.6041 (18)	0.8591 (8)	0.3299 (7)	0.059 (3)
C1	0.6219 (15)	0.8208 (7)	0.7023 (6)	0.037 (2)
C2	0.4607 (14)	0.8105 (7)	0.7522 (6)	0.036 (2)
C3	0.4664 (16)	0.8505 (9)	0.8268 (8)	0.053 (3)
H3	0.3670	0.8395	0.8618	0.064*
C4	0.6097 (16)	0.9068 (8)	0.8548 (7)	0.043 (3)
H4	0.6047	0.9353	0.9057	0.052*
C5	0.7635 (17)	0.9194 (8)	0.8029 (7)	0.045 (3)
C6	0.7729 (15)	0.8754 (7)	0.7315 (7)	0.040 (3)
H6	0.8810	0.8807	0.7005	0.048*
C7	0.6493 (15)	0.7739 (8)	0.6244 (7)	0.040 (3)
H7	0.7732	0.7719	0.6063	0.048*
C8	0.5844 (16)	0.6918 (8)	0.5030 (6)	0.041 (3)
H8A	0.7218	0.6867	0.5040	0.050*
H8B	0.5322	0.6321	0.5018	0.050*
C9	0.5214 (16)	0.7384 (7)	0.4269 (6)	0.040 (3)
H9A	0.3855	0.7490	0.4280	0.048*
H9B	0.5454	0.7012	0.3794	0.048*
C10	0.6226 (17)	0.8251 (8)	0.4181 (6)	0.043 (3)
H10A	0.7560	0.8176	0.4337	0.052*
H10B	0.5695	0.8685	0.4552	0.052*
C11	0.712 (3)	0.9462 (11)	0.3231 (11)	0.104 (7)
H11A	0.7465	0.9552	0.2667	0.157*
H11B	0.8255	0.9439	0.3580	0.157*
H11C	0.6336	0.9944	0.3402	0.157*
C12	0.402 (2)	0.8725 (12)	0.3032 (11)	0.082 (5)
H12A	0.3435	0.9129	0.3404	0.122*
H12B	0.3369	0.8165	0.3035	0.122*
H12C	0.3961	0.8968	0.2482	0.122*
H2	0.689 (16)	0.830 (9)	0.300 (8)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0336 (7)	0.0527 (9)	0.0387 (7)	−0.0029 (6)	0.0054 (5)	0.0014 (6)
Br1	0.0608 (9)	0.0527 (8)	0.0617 (9)	−0.0156 (6)	0.0011 (6)	−0.0087 (6)
Br2	0.0595 (8)	0.0585 (9)	0.0606 (9)	−0.0136 (6)	−0.0027 (6)	0.0019 (6)
Br3	0.0938 (15)	0.1062 (16)	0.1200 (18)	0.0158 (11)	0.0028 (12)	−0.0044 (12)
O1	0.045 (5)	0.065 (5)	0.040 (4)	−0.015 (4)	0.020 (4)	−0.007 (4)
N1	0.034 (5)	0.043 (5)	0.035 (5)	0.003 (4)	0.008 (4)	0.000 (4)
N2	0.075 (8)	0.056 (7)	0.046 (7)	−0.011 (6)	0.010 (5)	0.006 (5)
C1	0.038 (6)	0.041 (6)	0.032 (5)	−0.004 (5)	0.014 (4)	0.002 (5)
C2	0.031 (5)	0.043 (6)	0.033 (6)	−0.001 (5)	0.009 (4)	−0.003 (5)
C3	0.035 (6)	0.075 (9)	0.052 (7)	−0.012 (6)	0.025 (5)	−0.015 (6)
C4	0.052 (7)	0.041 (6)	0.037 (6)	0.003 (5)	0.014 (5)	−0.012 (5)
C5	0.046 (7)	0.039 (6)	0.048 (7)	−0.003 (5)	0.000 (5)	−0.005 (5)
C6	0.034 (6)	0.051 (7)	0.037 (6)	0.003 (5)	0.015 (5)	0.000 (5)
C7	0.028 (5)	0.053 (7)	0.038 (6)	0.000 (5)	0.008 (5)	0.003 (5)
C8	0.042 (6)	0.049 (7)	0.034 (6)	0.001 (5)	0.007 (5)	−0.008 (5)
C9	0.035 (6)	0.052 (7)	0.032 (6)	−0.001 (5)	0.008 (4)	−0.004 (5)
C10	0.056 (7)	0.054 (7)	0.020 (5)	−0.011 (6)	0.007 (5)	0.003 (5)
C11	0.17 (2)	0.073 (11)	0.068 (11)	−0.055 (12)	0.009 (12)	0.021 (9)
C12	0.078 (11)	0.091 (12)	0.077 (11)	0.027 (9)	0.022 (9)	0.011 (9)

Geometric parameters (Å, º)

Zn1—O1	1.943 (8)	C4—H4	0.93
Zn1—N1	2.015 (9)	C5—C6	1.334 (15)
Zn1—Br2	2.336 (3)	C6—H6	0.93
Zn1—Br3	2.391 (3)	C7—H7	0.93
Br1—C5	1.906 (12)	C8—C9	1.470 (15)
O1—C2	1.349 (13)	C8—H8A	0.97
N1—C7	1.236 (14)	C8—H8B	0.97
N1—C8	1.483 (13)	C9—C10	1.496 (15)
N2—C12	1.48 (2)	C9—H9A	0.97
N2—C10	1.517 (14)	C9—H9B	0.97
N2—C11	1.521 (18)	C10—H10A	0.97
N2—H2	0.90 (12)	C10—H10B	0.97
C1—C6	1.410 (15)	C11—H11A	0.96
C1—C2	1.424 (14)	C11—H11B	0.96
C1—C7	1.463 (15)	C11—H11C	0.96
C2—C3	1.347 (15)	C12—H12A	0.96
C3—C4	1.381 (17)	C12—H12B	0.96
C3—H3	0.93	C12—H12C	0.96
C4—C5	1.406 (16)
O1—Zn1—N1	94.4 (3)	N1—C7—C1	127.6 (10)
O1—Zn1—Br2	110.4 (2)	N1—C7—H7	116.2
N1—Zn1—Br2	112.5 (3)	C1—C7—H7	116.2
O1—Zn1—Br3	116.7 (3)	C9—C8—N1	113.7 (9)
N1—Zn1—Br3	105.7 (3)	C9—C8—H8A	108.8
Br2—Zn1—Br3	115.19 (9)	N1—C8—H8A	108.8
C2—O1—Zn1	119.7 (6)	C9—C8—H8B	108.8
C7—N1—C8	119.4 (9)	N1—C8—H8B	108.8
C7—N1—Zn1	119.1 (7)	H8A—C8—H8B	107.7
C8—N1—Zn1	121.4 (7)	C8—C9—C10	111.4 (9)
C12—N2—C10	111.7 (11)	C8—C9—H9A	109.4
C12—N2—C11	109.8 (13)	C10—C9—H9A	109.4
C10—N2—C11	109.4 (11)	C8—C9—H9B	109.4
C12—N2—H2	124 (10)	C10—C9—H9B	109.4
C10—N2—H2	108 (10)	H9A—C9—H9B	108.0
C11—N2—H2	92 (10)	C9—C10—N2	111.0 (9)
C6—C1—C2	118.7 (9)	C9—C10—H10A	109.4
C6—C1—C7	116.6 (9)	N2—C10—H10A	109.4
C2—C1—C7	124.6 (10)	C9—C10—H10B	109.4
C3—C2—O1	120.7 (9)	N2—C10—H10B	109.4
C3—C2—C1	117.3 (10)	H10A—C10—H10B	108.0
O1—C2—C1	121.9 (9)	N2—C11—H11A	109.5
C2—C3—C4	124.4 (10)	N2—C11—H11B	109.5
C2—C3—H3	117.8	H11A—C11—H11B	109.5
C4—C3—H3	117.8	N2—C11—H11C	109.5
C3—C4—C5	117.1 (10)	H11A—C11—H11C	109.5
C3—C4—H4	121.5	H11B—C11—H11C	109.5
C5—C4—H4	121.5	N2—C12—H12A	109.5
C6—C5—C4	120.9 (11)	N2—C12—H12B	109.5
C6—C5—Br1	121.5 (9)	H12A—C12—H12B	109.5
C4—C5—Br1	117.5 (8)	N2—C12—H12C	109.5
C5—C6—C1	121.2 (10)	H12A—C12—H12C	109.5
C5—C6—H6	119.4	H12B—C12—H12C	109.5
C1—C6—H6	119.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1^i	0.90 (12)	2.01 (13)	2.872 (14)	162 (14)

Symmetry code: (i) x+1/2, −y+3/2, z−1/2.