Bis(benzo[h]quinolin-10-olato-κ²N,O)bromidomanganese(III)

The title compound, [MnBr(C₁₃H₈NO)₂], consists of a manganese(III) atom, which is coordinated by one bromido and two benzo[h]quinolin-10-olato ligands. The Mn^III complex exhibits a distorted square-pyramidal coordination geometry with the Br ligand in the apical position. Neighbouring complexes are held together by π–π inter­actions and weak C—H...Br hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.114
• Data-to-parameter ratio = 21.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.16 Report
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1       ..BR1      .       3.03 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2       ..BR1      .       2.96 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)     0.0018 Degree
PLAT333_ALERT_2_G Large Aver C6-Ring C-C Dist C4       -C13      .       1.42 Ang.
PLAT333_ALERT_2_G Large Aver C6-Ring C-C Dist C17      -C26      .       1.42 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  C16      ..C24              3.19 Ang.
                                                1-x,1-y,2-z  =      2_667 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         16 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          7 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         11 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   1 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
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2015) and Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

Bis(benzo[h]quinolin-10-olato-κ²N,O)bromidomanganese(III)

Crystal data

[MnBr(C13H8NO)2]	Z = 2
Mr = 523.26	F(000) = 524
Triclinic, P1	Dx = 1.771 Mg m^−3
a = 7.3303 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5266 (7) Å	Cell parameters from 9946 reflections
c = 13.8432 (10) Å	θ = 2.3–30.7°
α = 76.9612 (18)°	µ = 2.74 mm^−1
β = 78.8220 (18)°	T = 150 K
γ = 72.0364 (18)°	Prism, brown
V = 980.97 (12) Å^3	0.41 × 0.23 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer	6093 independent reflections
Radiation source: fine-focus sealed tube	5110 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	Rint = 0.036
ω scans	θmax = 30.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −10→10
Tmin = 0.40, Tmax = 0.72	k = −15→15
42556 measured reflections	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0649P)^2 + 0.8212P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
6093 reflections	Δρmax = 0.96 e Å^−3
289 parameters	Δρmin = −0.44 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.86544 (3)	0.86413 (2)	0.75405 (2)	0.02263 (8)
C1	0.3671 (3)	0.8124 (2)	0.63030 (17)	0.0194 (4)
H1	0.300222	0.800888	0.696278	0.023*
C2	0.2593 (4)	0.8771 (3)	0.55156 (18)	0.0217 (5)
H2	0.121977	0.905678	0.563390	0.026*
C3	0.3551 (4)	0.8984 (3)	0.45723 (18)	0.0217 (5)
H3	0.284870	0.945580	0.402862	0.026*
C4	0.5574 (4)	0.8506 (2)	0.44051 (17)	0.0192 (4)
C5	0.6605 (4)	0.8746 (3)	0.34209 (18)	0.0239 (5)
H5	0.591514	0.924163	0.287706	0.029*
C6	0.8552 (4)	0.8272 (3)	0.32630 (18)	0.0245 (5)
H6	0.922096	0.848863	0.261538	0.029*
C7	0.9628 (4)	0.7450 (2)	0.40491 (17)	0.0206 (4)
C8	1.1609 (4)	0.6838 (3)	0.38329 (19)	0.0239 (5)
H8	1.225262	0.704000	0.317627	0.029*
C9	1.2636 (4)	0.5947 (3)	0.45581 (19)	0.0256 (5)
H9	1.397247	0.551630	0.439627	0.031*
C10	1.1717 (4)	0.5675 (3)	0.55334 (18)	0.0230 (5)
H10	1.243939	0.506170	0.603124	0.028*
C11	0.9763 (3)	0.6288 (2)	0.57866 (17)	0.0179 (4)
C12	0.8661 (3)	0.7198 (2)	0.50432 (16)	0.0172 (4)
C13	0.6599 (3)	0.7784 (2)	0.52252 (16)	0.0163 (4)
C14	0.8677 (3)	0.4264 (2)	0.85999 (17)	0.0185 (4)
H14	0.905836	0.409618	0.793397	0.022*
C15	0.9360 (3)	0.3231 (2)	0.93801 (18)	0.0200 (4)
H15	1.015414	0.236871	0.924909	0.024*
C16	0.8865 (3)	0.3481 (2)	1.03367 (17)	0.0193 (4)
H16	0.935733	0.280183	1.087564	0.023*
C17	0.7636 (3)	0.4735 (2)	1.05221 (16)	0.0171 (4)
C18	0.7158 (3)	0.5039 (3)	1.15135 (17)	0.0209 (4)
H18	0.766023	0.437282	1.205665	0.025*
C19	0.6004 (4)	0.6261 (3)	1.16818 (17)	0.0216 (4)
H19	0.576532	0.646090	1.233820	0.026*
C20	0.5124 (3)	0.7270 (2)	1.08935 (17)	0.0188 (4)
C21	0.3829 (4)	0.8493 (3)	1.11064 (18)	0.0225 (5)
H21	0.360503	0.868322	1.176527	0.027*
C22	0.2875 (4)	0.9428 (3)	1.03660 (19)	0.0245 (5)
H22	0.199403	1.025525	1.051751	0.029*
C23	0.3201 (4)	0.9160 (2)	0.93963 (18)	0.0221 (5)
H23	0.251384	0.979792	0.889550	0.027*
C24	0.4518 (3)	0.7971 (2)	0.91527 (16)	0.0171 (4)
C25	0.5548 (3)	0.7003 (2)	0.98981 (16)	0.0160 (4)
C26	0.6900 (3)	0.5732 (2)	0.97060 (16)	0.0155 (4)
Mn1	0.69313 (5)	0.69516 (4)	0.74703 (2)	0.01740 (9)
N1	0.5603 (3)	0.76591 (19)	0.61740 (14)	0.0166 (3)
N2	0.7511 (3)	0.54816 (19)	0.87462 (14)	0.0162 (3)
O1	0.8970 (3)	0.59267 (18)	0.67213 (12)	0.0215 (3)
O2	0.4684 (2)	0.77507 (17)	0.82180 (12)	0.0196 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02412 (13)	0.02379 (13)	0.01929 (12)	−0.00630 (9)	−0.00649 (9)	0.00014 (9)
C1	0.0198 (10)	0.0235 (11)	0.0154 (10)	−0.0071 (9)	−0.0062 (8)	0.0002 (8)
C2	0.0196 (11)	0.0251 (11)	0.0206 (11)	−0.0057 (9)	−0.0080 (9)	−0.0009 (9)
C3	0.0240 (11)	0.0238 (11)	0.0179 (10)	−0.0060 (9)	−0.0109 (9)	0.0014 (8)
C4	0.0260 (11)	0.0174 (10)	0.0149 (10)	−0.0062 (8)	−0.0074 (8)	−0.0002 (8)
C5	0.0315 (13)	0.0254 (11)	0.0140 (10)	−0.0077 (10)	−0.0073 (9)	0.0017 (9)
C6	0.0321 (13)	0.0264 (12)	0.0135 (10)	−0.0085 (10)	−0.0031 (9)	−0.0001 (9)
C7	0.0258 (11)	0.0211 (10)	0.0168 (10)	−0.0088 (9)	−0.0027 (9)	−0.0039 (8)
C8	0.0248 (12)	0.0286 (12)	0.0188 (11)	−0.0091 (10)	0.0004 (9)	−0.0058 (9)
C9	0.0205 (11)	0.0316 (13)	0.0232 (12)	−0.0049 (10)	0.0001 (9)	−0.0076 (10)
C10	0.0226 (11)	0.0250 (11)	0.0191 (11)	−0.0008 (9)	−0.0052 (9)	−0.0052 (9)
C11	0.0204 (10)	0.0177 (10)	0.0153 (9)	−0.0026 (8)	−0.0039 (8)	−0.0045 (8)
C12	0.0211 (10)	0.0150 (9)	0.0154 (10)	−0.0049 (8)	−0.0035 (8)	−0.0019 (7)
C13	0.0205 (10)	0.0144 (9)	0.0141 (9)	−0.0052 (8)	−0.0043 (8)	−0.0006 (7)
C14	0.0206 (10)	0.0173 (10)	0.0168 (10)	−0.0056 (8)	−0.0044 (8)	0.0006 (8)
C15	0.0185 (10)	0.0157 (10)	0.0230 (11)	−0.0042 (8)	−0.0044 (8)	0.0028 (8)
C16	0.0169 (10)	0.0203 (10)	0.0183 (10)	−0.0057 (8)	−0.0064 (8)	0.0055 (8)
C17	0.0143 (9)	0.0209 (10)	0.0159 (9)	−0.0074 (8)	−0.0044 (8)	0.0027 (8)
C18	0.0191 (10)	0.0284 (12)	0.0147 (10)	−0.0092 (9)	−0.0055 (8)	0.0036 (8)
C19	0.0202 (10)	0.0308 (12)	0.0143 (10)	−0.0086 (9)	−0.0031 (8)	−0.0022 (9)
C20	0.0184 (10)	0.0234 (11)	0.0164 (10)	−0.0083 (8)	−0.0037 (8)	−0.0026 (8)
C21	0.0251 (11)	0.0253 (11)	0.0184 (10)	−0.0088 (9)	−0.0006 (9)	−0.0056 (9)
C22	0.0277 (12)	0.0185 (11)	0.0233 (12)	−0.0034 (9)	0.0016 (9)	−0.0040 (9)
C23	0.0240 (11)	0.0183 (10)	0.0187 (11)	−0.0025 (9)	−0.0008 (9)	0.0009 (8)
C24	0.0156 (9)	0.0187 (10)	0.0149 (9)	−0.0049 (8)	−0.0008 (8)	0.0005 (8)
C25	0.0136 (9)	0.0184 (10)	0.0154 (9)	−0.0049 (8)	−0.0027 (7)	−0.0003 (8)
C26	0.0135 (9)	0.0194 (10)	0.0146 (9)	−0.0074 (8)	−0.0044 (7)	0.0011 (8)
Mn1	0.01791 (17)	0.01906 (17)	0.01235 (16)	−0.00190 (13)	−0.00333 (12)	−0.00042 (12)
N1	0.0190 (9)	0.0171 (8)	0.0132 (8)	−0.0050 (7)	−0.0057 (7)	0.0013 (6)
N2	0.0171 (8)	0.0163 (8)	0.0151 (8)	−0.0049 (7)	−0.0052 (7)	0.0002 (7)
O1	0.0232 (8)	0.0224 (8)	0.0126 (7)	0.0019 (6)	−0.0026 (6)	−0.0018 (6)
O2	0.0177 (7)	0.0226 (8)	0.0134 (7)	−0.0006 (6)	−0.0018 (6)	−0.0003 (6)

Geometric parameters (Å, º)

Br1—Mn1	2.5060 (5)	C14—H14	0.9500
C1—N1	1.338 (3)	C15—C16	1.366 (3)
C1—C2	1.394 (3)	C15—H15	0.9500
C1—H1	0.9500	C16—C17	1.397 (3)
C2—C3	1.363 (3)	C16—H16	0.9500
C2—H2	0.9500	C17—C26	1.422 (3)
C3—C4	1.401 (3)	C17—C18	1.432 (3)
C3—H3	0.9500	C18—C19	1.346 (4)
C4—C13	1.421 (3)	C18—H18	0.9500
C4—C5	1.433 (3)	C19—C20	1.436 (3)
C5—C6	1.350 (4)	C19—H19	0.9500
C5—H5	0.9500	C20—C21	1.398 (3)
C6—C7	1.429 (3)	C20—C25	1.424 (3)
C6—H6	0.9500	C21—C22	1.381 (4)
C7—C8	1.398 (4)	C21—H21	0.9500
C7—C12	1.428 (3)	C22—C23	1.394 (4)
C8—C9	1.373 (4)	C22—H22	0.9500
C8—H8	0.9500	C23—C24	1.389 (3)
C9—C10	1.397 (4)	C23—H23	0.9500
C9—H9	0.9500	C24—O2	1.341 (3)
C10—C11	1.388 (3)	C24—C25	1.424 (3)
C10—H10	0.9500	C25—C26	1.444 (3)
C11—O1	1.334 (3)	C26—N2	1.375 (3)
C11—C12	1.425 (3)	Mn1—O2	1.8356 (17)
C12—C13	1.441 (3)	Mn1—O1	1.8389 (17)
C13—N1	1.373 (3)	Mn1—N2	2.0849 (19)
C14—N2	1.337 (3)	Mn1—N1	2.0858 (18)
C14—C15	1.394 (3)
N1—C1—C2	123.1 (2)	C16—C17—C26	119.1 (2)
N1—C1—H1	118.4	C16—C17—C18	120.9 (2)
C2—C1—H1	118.4	C26—C17—C18	119.9 (2)
C3—C2—C1	118.6 (2)	C19—C18—C17	120.5 (2)
C3—C2—H2	120.7	C19—C18—H18	119.7
C1—C2—H2	120.7	C17—C18—H18	119.7
C2—C3—C4	120.0 (2)	C18—C19—C20	121.6 (2)
C2—C3—H3	120.0	C18—C19—H19	119.2
C4—C3—H3	120.0	C20—C19—H19	119.2
C3—C4—C13	119.2 (2)	C21—C20—C25	120.3 (2)
C3—C4—C5	120.6 (2)	C21—C20—C19	120.2 (2)
C13—C4—C5	120.1 (2)	C25—C20—C19	119.5 (2)
C6—C5—C4	120.3 (2)	C22—C21—C20	120.5 (2)
C6—C5—H5	119.8	C22—C21—H21	119.8
C4—C5—H5	119.8	C20—C21—H21	119.8
C5—C6—C7	121.4 (2)	C21—C22—C23	120.1 (2)
C5—C6—H6	119.3	C21—C22—H22	119.9
C7—C6—H6	119.3	C23—C22—H22	119.9
C8—C7—C12	120.1 (2)	C24—C23—C22	120.9 (2)
C8—C7—C6	119.8 (2)	C24—C23—H23	119.6
C12—C7—C6	120.0 (2)	C22—C23—H23	119.6
C9—C8—C7	120.8 (2)	O2—C24—C23	117.5 (2)
C9—C8—H8	119.6	O2—C24—C25	122.3 (2)
C7—C8—H8	119.6	C23—C24—C25	120.1 (2)
C8—C9—C10	120.0 (2)	C24—C25—C20	118.0 (2)
C8—C9—H9	120.0	C24—C25—C26	123.1 (2)
C10—C9—H9	120.0	C20—C25—C26	118.7 (2)
C11—C10—C9	121.0 (2)	N2—C26—C17	119.6 (2)
C11—C10—H10	119.5	N2—C26—C25	121.04 (19)
C9—C10—H10	119.5	C17—C26—C25	119.4 (2)
O1—C11—C10	117.4 (2)	O2—Mn1—O1	170.00 (9)
O1—C11—C12	122.6 (2)	O2—Mn1—N2	86.73 (7)
C10—C11—C12	119.9 (2)	O1—Mn1—N2	90.35 (8)
C11—C12—C7	118.1 (2)	O2—Mn1—N1	90.70 (8)
C11—C12—C13	123.2 (2)	O1—Mn1—N1	86.90 (8)
C7—C12—C13	118.5 (2)	N2—Mn1—N1	149.10 (8)
N1—C13—C4	119.3 (2)	O2—Mn1—Br1	95.03 (6)
N1—C13—C12	121.41 (19)	O1—Mn1—Br1	94.96 (6)
C4—C13—C12	119.3 (2)	N2—Mn1—Br1	104.39 (5)
N2—C14—C15	123.0 (2)	N1—Mn1—Br1	106.51 (6)
N2—C14—H14	118.5	C1—N1—C13	119.53 (19)
C15—C14—H14	118.5	C1—N1—Mn1	116.41 (15)
C16—C15—C14	118.7 (2)	C13—N1—Mn1	123.77 (15)
C16—C15—H15	120.6	C14—N2—C26	119.37 (19)
C14—C15—H15	120.6	C14—N2—Mn1	116.60 (15)
C15—C16—C17	120.0 (2)	C26—N2—Mn1	123.79 (15)
C15—C16—H16	120.0	C11—O1—Mn1	128.18 (15)
C17—C16—H16	120.0	C24—O2—Mn1	126.02 (15)
N1—C1—C2—C3	−2.4 (4)	C20—C21—C22—C23	−0.2 (4)
C1—C2—C3—C4	2.6 (4)	C21—C22—C23—C24	−1.6 (4)
C2—C3—C4—C13	0.9 (4)	C22—C23—C24—O2	176.7 (2)
C2—C3—C4—C5	−178.7 (2)	C22—C23—C24—C25	0.4 (4)
C3—C4—C5—C6	−179.4 (2)	O2—C24—C25—C20	−173.6 (2)
C13—C4—C5—C6	1.0 (4)	C23—C24—C25—C20	2.5 (3)
C4—C5—C6—C7	4.0 (4)	O2—C24—C25—C26	2.2 (3)
C5—C6—C7—C8	172.1 (3)	C23—C24—C25—C26	178.4 (2)
C5—C6—C7—C12	−4.7 (4)	C21—C20—C25—C24	−4.3 (3)
C12—C7—C8—C9	2.6 (4)	C19—C20—C25—C24	174.4 (2)
C6—C7—C8—C9	−174.1 (2)	C21—C20—C25—C26	179.7 (2)
C7—C8—C9—C10	−2.0 (4)	C19—C20—C25—C26	−1.6 (3)
C8—C9—C10—C11	0.3 (4)	C16—C17—C26—N2	−4.5 (3)
C9—C10—C11—O1	176.9 (2)	C18—C17—C26—N2	173.8 (2)
C9—C10—C11—C12	0.7 (4)	C16—C17—C26—C25	176.7 (2)
O1—C11—C12—C7	−176.1 (2)	C18—C17—C26—C25	−5.0 (3)
C10—C11—C12—C7	0.0 (3)	C24—C25—C26—N2	11.0 (3)
O1—C11—C12—C13	−1.5 (3)	C20—C25—C26—N2	−173.3 (2)
C10—C11—C12—C13	174.6 (2)	C24—C25—C26—C17	−170.3 (2)
C8—C7—C12—C11	−1.6 (3)	C20—C25—C26—C17	5.5 (3)
C6—C7—C12—C11	175.1 (2)	C2—C1—N1—C13	−1.6 (3)
C8—C7—C12—C13	−176.4 (2)	C2—C1—N1—Mn1	172.44 (19)
C6—C7—C12—C13	0.3 (3)	C4—C13—N1—C1	5.2 (3)
C3—C4—C13—N1	−4.9 (3)	C12—C13—N1—C1	−174.8 (2)
C5—C4—C13—N1	174.7 (2)	C4—C13—N1—Mn1	−168.38 (16)
C3—C4—C13—C12	175.1 (2)	C12—C13—N1—Mn1	11.6 (3)
C5—C4—C13—C12	−5.3 (3)	C15—C14—N2—C26	−1.8 (3)
C11—C12—C13—N1	10.0 (3)	C15—C14—N2—Mn1	172.88 (18)
C7—C12—C13—N1	−175.5 (2)	C17—C26—N2—C14	5.0 (3)
C11—C12—C13—C4	−170.0 (2)	C25—C26—N2—C14	−176.2 (2)
C7—C12—C13—C4	4.5 (3)	C17—C26—N2—Mn1	−169.30 (15)
N2—C14—C15—C16	−2.0 (4)	C25—C26—N2—Mn1	9.5 (3)
C14—C15—C16—C17	2.5 (3)	C10—C11—O1—Mn1	150.17 (19)
C15—C16—C17—C26	0.7 (3)	C12—C11—O1—Mn1	−33.7 (3)
C15—C16—C17—C18	−177.5 (2)	N2—Mn1—O1—C11	−169.3 (2)
C16—C17—C18—C19	178.6 (2)	N1—Mn1—O1—C11	41.5 (2)
C26—C17—C18—C19	0.4 (3)	Br1—Mn1—O1—C11	−64.8 (2)
C17—C18—C19—C20	3.6 (4)	C23—C24—O2—Mn1	143.34 (18)
C18—C19—C20—C21	175.7 (2)	C25—C24—O2—Mn1	−40.4 (3)
C18—C19—C20—C25	−3.0 (3)	N2—Mn1—O2—C24	45.79 (18)
C25—C20—C21—C22	3.2 (4)	N1—Mn1—O2—C24	−165.02 (18)
C19—C20—C21—C22	−175.5 (2)	Br1—Mn1—O2—C24	−58.38 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br1^i	0.95	3.03	3.674 (2)	126
C2—H2···Br1^i	0.95	2.96	3.626 (3)	128

Symmetry code: (i) x−1, y, z.