Bis[4-bromo-2-(cyclo­propyl­imino­meth­yl)phenolato]zinc(II)

In the mononuclear title complex, [Zn(C₁₀H₉BrNO)₂], the Zn^II atom is four-coordinated by two imine N and two phenolate O atoms from two Schiff base ligands in a distorted tetra­hedral geometry.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.043
• wR factor = 0.102
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.70 Ratio

Author Response: This is probably caused by the tensile force of the cyclopropyl ring.

Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.29 Ratio
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C19
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C20
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C18

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.346     0.538
            Tmin and Tmax expected:      0.302     0.538
            RR =      1.147
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.15
PLAT213_ALERT_2_C Atom C19     has ADP max/min Ratio .............       3.20 prolat
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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

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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bis[4-bromo-2-(cyclopropyliminomethyl)phenolato]zinc(II)

Crystal data

[Zn(C10H9BrNO)2]	F(000) = 2144
Mr = 543.55	Dx = 1.779 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4849 reflections
a = 23.260 (2) Å	θ = 2.3–23.6°
b = 13.305 (2) Å	µ = 5.16 mm^−1
c = 13.119 (3) Å	T = 298 K
V = 4060.0 (12) Å^3	Block, colourless
Z = 8	0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4619 independent reflections
Radiation source: fine-focus sealed tube	2693 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −29→28
Tmin = 0.346, Tmax = 0.538	k = −16→17
21839 measured reflections	l = −16→16

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0401P)^2 + 2.1967P] where P = (Fo^2 + 2Fc^2)/3
4619 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.78 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	0.76037 (2)	0.13990 (3)	0.33956 (4)	0.03721 (14)
Br1	0.51249 (2)	−0.10138 (4)	0.10635 (5)	0.0729 (2)
Br2	0.98190 (3)	0.41105 (5)	0.62473 (4)	0.0797 (2)
O1	0.69883 (12)	0.1778 (2)	0.2504 (2)	0.0451 (7)
O2	0.83049 (12)	0.2094 (2)	0.3144 (2)	0.0455 (8)
N1	0.75946 (13)	−0.0070 (2)	0.3064 (2)	0.0366 (8)
N2	0.74880 (14)	0.1859 (3)	0.4843 (2)	0.0406 (9)
C1	0.66665 (15)	0.0079 (3)	0.2194 (3)	0.0315 (9)
C2	0.65917 (17)	0.1142 (3)	0.2201 (3)	0.0363 (10)
C3	0.60622 (18)	0.1511 (3)	0.1862 (3)	0.0439 (11)
H3	0.6000	0.2201	0.1866	0.053*
C4	0.56289 (18)	0.0888 (4)	0.1522 (3)	0.0467 (11)
H4	0.5280	0.1156	0.1309	0.056*
C5	0.57194 (17)	−0.0138 (3)	0.1503 (3)	0.0421 (10)
C6	0.62259 (16)	−0.0534 (3)	0.1827 (3)	0.0381 (10)
H6	0.6280	−0.1226	0.1804	0.046*
C7	0.71656 (16)	−0.0441 (3)	0.2572 (3)	0.0344 (9)
H7	0.7180	−0.1128	0.2446	0.041*
C8	0.80398 (19)	−0.0748 (3)	0.3382 (3)	0.0506 (12)
H8	0.7965	−0.1462	0.3256	0.061*
C9	0.8646 (2)	−0.0430 (5)	0.3295 (5)	0.087 (2)
H9A	0.8927	−0.0934	0.3101	0.105*
H9B	0.8722	0.0240	0.3036	0.105*
C10	0.8380 (3)	−0.0517 (4)	0.4305 (5)	0.0842 (19)
H10A	0.8292	0.0099	0.4668	0.101*
H10B	0.8497	−0.1075	0.4733	0.101*
C11	0.84267 (17)	0.2690 (3)	0.4872 (3)	0.0345 (10)
C12	0.86212 (18)	0.2509 (3)	0.3863 (3)	0.0384 (10)
C13	0.91874 (19)	0.2805 (3)	0.3622 (3)	0.0447 (11)
H13	0.9331	0.2669	0.2975	0.054*
C14	0.95302 (19)	0.3284 (3)	0.4313 (4)	0.0516 (12)
H14	0.9900	0.3480	0.4130	0.062*
C15	0.93305 (19)	0.3477 (3)	0.5280 (4)	0.0477 (12)
C16	0.87939 (18)	0.3185 (3)	0.5561 (3)	0.0423 (10)
H16	0.8667	0.3314	0.6221	0.051*
C17	0.78764 (18)	0.2398 (3)	0.5272 (3)	0.0397 (10)
H17	0.7791	0.2629	0.5924	0.048*
C18	0.6980 (2)	0.1634 (4)	0.5433 (3)	0.0584 (14)
H18	0.6954	0.1962	0.6101	0.070*
C19	0.6734 (4)	0.0622 (6)	0.5364 (7)	0.147 (4)
H19A	0.6921	0.0143	0.4915	0.176*
H19B	0.6571	0.0333	0.5978	0.176*
C20	0.6431 (3)	0.1469 (8)	0.4895 (5)	0.135 (4)
H20A	0.6082	0.1704	0.5221	0.162*
H20B	0.6432	0.1514	0.4157	0.162*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0462 (3)	0.0354 (3)	0.0301 (3)	−0.0062 (2)	−0.0045 (2)	−0.0029 (2)
Br1	0.0444 (3)	0.0832 (4)	0.0912 (5)	−0.0143 (3)	−0.0187 (3)	−0.0090 (3)
Br2	0.0779 (4)	0.0970 (5)	0.0641 (4)	−0.0389 (3)	−0.0266 (3)	−0.0034 (3)
O1	0.0579 (18)	0.0338 (16)	0.0435 (19)	−0.0032 (14)	−0.0127 (15)	0.0019 (14)
O2	0.0556 (18)	0.0536 (19)	0.0274 (17)	−0.0166 (15)	0.0024 (14)	−0.0075 (14)
N1	0.0393 (18)	0.0364 (19)	0.034 (2)	0.0025 (16)	−0.0068 (16)	−0.0019 (15)
N2	0.048 (2)	0.042 (2)	0.033 (2)	−0.0089 (17)	0.0003 (16)	−0.0025 (16)
C1	0.039 (2)	0.030 (2)	0.025 (2)	−0.0019 (18)	−0.0018 (17)	−0.0034 (18)
C2	0.046 (2)	0.042 (3)	0.021 (2)	0.000 (2)	−0.0016 (18)	−0.0042 (19)
C3	0.051 (3)	0.040 (3)	0.041 (3)	0.012 (2)	−0.003 (2)	−0.001 (2)
C4	0.039 (2)	0.067 (3)	0.035 (3)	0.013 (2)	−0.0021 (19)	−0.001 (2)
C5	0.036 (2)	0.053 (3)	0.037 (3)	−0.006 (2)	0.0007 (19)	−0.005 (2)
C6	0.039 (2)	0.042 (3)	0.032 (2)	−0.001 (2)	0.0012 (19)	−0.0030 (19)
C7	0.043 (2)	0.028 (2)	0.033 (2)	0.0005 (18)	−0.0018 (19)	−0.0045 (18)
C8	0.054 (3)	0.039 (3)	0.059 (3)	0.007 (2)	−0.018 (2)	−0.002 (2)
C9	0.048 (3)	0.094 (5)	0.120 (6)	0.010 (3)	−0.036 (4)	−0.005 (4)
C10	0.101 (5)	0.080 (4)	0.072 (4)	0.029 (4)	−0.055 (4)	−0.014 (3)
C11	0.045 (2)	0.028 (2)	0.030 (2)	−0.0035 (19)	−0.0070 (19)	0.0010 (18)
C12	0.047 (2)	0.040 (2)	0.029 (3)	−0.004 (2)	−0.0061 (19)	0.005 (2)
C13	0.050 (3)	0.050 (3)	0.034 (3)	−0.004 (2)	0.001 (2)	0.007 (2)
C14	0.044 (3)	0.054 (3)	0.057 (3)	−0.013 (2)	−0.008 (2)	0.004 (3)
C15	0.052 (3)	0.044 (3)	0.047 (3)	−0.012 (2)	−0.017 (2)	0.002 (2)
C16	0.054 (3)	0.038 (3)	0.035 (3)	−0.004 (2)	−0.008 (2)	−0.001 (2)
C17	0.050 (3)	0.040 (3)	0.029 (2)	−0.004 (2)	0.001 (2)	−0.004 (2)
C18	0.065 (3)	0.075 (4)	0.035 (3)	−0.026 (3)	0.018 (2)	−0.026 (2)
C19	0.182 (10)	0.116 (6)	0.143 (8)	−0.110 (6)	0.105 (7)	−0.072 (6)
C20	0.062 (4)	0.281 (12)	0.063 (5)	−0.077 (6)	0.020 (3)	−0.061 (6)

Geometric parameters (Å, º)

Zn1—O2	1.904 (3)	C8—H8	0.98
Zn1—O1	1.916 (3)	C9—C10	1.467 (8)
Zn1—N1	2.002 (3)	C9—H9A	0.97
Zn1—N2	2.013 (3)	C9—H9B	0.97
Br1—C5	1.898 (4)	C10—H10A	0.97
Br2—C15	1.900 (4)	C10—H10B	0.97
O1—C2	1.313 (4)	C11—C16	1.408 (5)
O2—C12	1.317 (4)	C11—C12	1.419 (5)
N1—C7	1.286 (4)	C11—C17	1.437 (5)
N1—C8	1.435 (5)	C12—C13	1.410 (6)
N2—C17	1.284 (5)	C13—C14	1.365 (6)
N2—C18	1.443 (5)	C13—H13	0.93
C1—C6	1.396 (5)	C14—C15	1.375 (6)
C1—C2	1.425 (5)	C14—H14	0.93
C1—C7	1.439 (5)	C15—C16	1.358 (6)
C2—C3	1.398 (5)	C16—H16	0.93
C3—C4	1.379 (6)	C17—H17	0.93
C3—H3	0.93	C18—C19	1.467 (7)
C4—C5	1.381 (6)	C18—C20	1.477 (8)
C4—H4	0.93	C18—H18	0.98
C5—C6	1.359 (5)	C19—C20	1.465 (11)
C6—H6	0.93	C19—H19A	0.97
C7—H7	0.93	C19—H19B	0.97
C8—C9	1.476 (7)	C20—H20A	0.97
C8—C10	1.479 (6)	C20—H20B	0.97
O2—Zn1—O1	113.95 (12)	H9A—C9—H9B	114.9
O2—Zn1—N1	116.46 (13)	C9—C10—C8	60.1 (3)
O1—Zn1—N1	96.69 (12)	C9—C10—H10A	117.8
O2—Zn1—N2	97.50 (12)	C8—C10—H10A	117.8
O1—Zn1—N2	113.33 (13)	C9—C10—H10B	117.8
N1—Zn1—N2	120.01 (14)	C8—C10—H10B	117.8
C2—O1—Zn1	122.7 (3)	H10A—C10—H10B	114.9
C12—O2—Zn1	123.9 (2)	C16—C11—C12	119.0 (4)
C7—N1—C8	117.7 (3)	C16—C11—C17	115.6 (4)
C7—N1—Zn1	119.4 (3)	C12—C11—C17	125.4 (4)
C8—N1—Zn1	122.9 (3)	O2—C12—C13	118.6 (4)
C17—N2—C18	117.1 (4)	O2—C12—C11	124.1 (4)
C17—N2—Zn1	119.3 (3)	C13—C12—C11	117.3 (4)
C18—N2—Zn1	123.5 (3)	C14—C13—C12	121.8 (4)
C6—C1—C2	119.5 (4)	C14—C13—H13	119.1
C6—C1—C7	115.5 (3)	C12—C13—H13	119.1
C2—C1—C7	125.0 (3)	C13—C14—C15	120.2 (4)
O1—C2—C3	119.3 (4)	C13—C14—H14	119.9
O1—C2—C1	123.7 (4)	C15—C14—H14	119.9
C3—C2—C1	117.0 (4)	C16—C15—C14	120.5 (4)
C4—C3—C2	122.4 (4)	C16—C15—Br2	119.6 (4)
C4—C3—H3	118.8	C14—C15—Br2	119.8 (3)
C2—C3—H3	118.8	C15—C16—C11	121.1 (4)
C3—C4—C5	119.2 (4)	C15—C16—H16	119.4
C3—C4—H4	120.4	C11—C16—H16	119.4
C5—C4—H4	120.4	N2—C17—C11	128.1 (4)
C6—C5—C4	120.7 (4)	N2—C17—H17	115.9
C6—C5—Br1	119.2 (3)	C11—C17—H17	115.9
C4—C5—Br1	120.1 (3)	N2—C18—C19	118.5 (5)
C5—C6—C1	121.2 (4)	N2—C18—C20	118.8 (4)
C5—C6—H6	119.4	C19—C18—C20	59.7 (5)
C1—C6—H6	119.4	N2—C18—H18	116.0
N1—C7—C1	127.9 (4)	C19—C18—H18	116.0
N1—C7—H7	116.1	C20—C18—H18	116.0
C1—C7—H7	116.1	C20—C19—C18	60.5 (4)
N1—C8—C9	119.1 (4)	C20—C19—H19A	117.7
N1—C8—C10	119.6 (4)	C18—C19—H19A	117.7
C9—C8—C10	59.5 (3)	C20—C19—H19B	117.7
N1—C8—H8	115.7	C18—C19—H19B	117.7
C9—C8—H8	115.7	H19A—C19—H19B	114.8
C10—C8—H8	115.7	C19—C20—C18	59.8 (5)
C10—C9—C8	60.3 (3)	C19—C20—H20A	117.8
C10—C9—H9A	117.7	C18—C20—H20A	117.8
C8—C9—H9A	117.7	C19—C20—H20B	117.8
C10—C9—H9B	117.7	C18—C20—H20B	117.8
C8—C9—H9B	117.7	H20A—C20—H20B	114.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1^i	0.98	2.54	3.488 (5)	162
C18—H18···O1^ii	0.98	2.49	3.442 (5)	163
C20—H20B···O1	0.97	2.55	3.419 (7)	149

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