Bis{2-[1-(adamantan-1-yl)ethyl­imino­meth­yl]phenolato-κO}dichloro­manganese(II)

In the title compound, [MnCl₂(C₁₉H₂₅NO)₂], each Mn^II ion is coordinated by two Cl⁻ ions and two O atoms from two 2-[1-(adamantan-1-yl)ethyl­imino­meth­yl]phenolate ligands in a distorted tetra­hedral geometry. The Mn atom lies on a twofold rotation axis. There are intra­molecular hydrogen-bonding inter­actions between the imino N and phenolate O atoms.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.130
• Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.51 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C14    -   C16     ..       6.94 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Mn1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8

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

   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
   0 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: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

Bis{2-[1-(adamantan-1-yl)ethyliminomethyl]phenolato-κO}dichloromanganese(II)

Crystal data

[MnCl2(C19H25NO)2]	F(000) = 1468
Mr = 692.64	Dx = 1.276 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 21347 reflections
a = 14.440 (3) Å	θ = 3.5–27.5°
b = 10.753 (2) Å	µ = 0.55 mm^−1
c = 23.222 (5) Å	T = 296 K
V = 3605.9 (13) Å^3	Prism, yellow
Z = 4	0.40 × 0.32 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	4106 independent reflections
Radiation source: fine-focus sealed tube	2967 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω scans	θmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.810, Tmax = 0.921	k = −13→13
31203 measured reflections	l = −29→30

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0717P)^2 + 0.4209P] where P = (Fo^2 + 2Fc^2)/3
4106 reflections	(Δ/σ)max = 0.001
205 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.20 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
Mn1	0.0000	0.54355 (4)	0.2500	0.05675 (16)
Cl1	0.05397 (4)	0.65920 (6)	0.32833 (3)	0.0825 (2)
O1	0.09590 (9)	0.41468 (14)	0.22707 (7)	0.0693 (4)
N1	0.16699 (12)	0.23218 (15)	0.28603 (7)	0.0632 (4)
H1A	0.1202	0.2794	0.2794	0.076*
C1	0.17450 (12)	0.42470 (17)	0.19932 (8)	0.0549 (4)
C2	0.24902 (13)	0.34408 (17)	0.21320 (7)	0.0541 (4)
C3	0.33416 (14)	0.3563 (2)	0.18389 (9)	0.0684 (5)
H3A	0.3830	0.3034	0.1930	0.082*
C4	0.34563 (16)	0.4444 (2)	0.14253 (9)	0.0754 (6)
H4A	0.4021	0.4522	0.1236	0.090*
C5	0.27312 (18)	0.5222 (2)	0.12883 (10)	0.0794 (6)
H5A	0.2812	0.5821	0.1004	0.095*
C6	0.18932 (16)	0.5131 (2)	0.15621 (10)	0.0721 (6)
H6A	0.1415	0.5667	0.1459	0.087*
C7	0.24067 (15)	0.2520 (2)	0.25647 (8)	0.0622 (5)
H7A	0.2921	0.2025	0.2640	0.075*
C8	0.13084 (15)	0.19511 (17)	0.38861 (8)	0.0605 (5)
C9	0.0450 (2)	0.2740 (3)	0.38654 (10)	0.0873 (7)
H9A	−0.0072	0.2238	0.3742	0.105*
H9B	0.0533	0.3407	0.3589	0.105*
C10	0.0251 (3)	0.3289 (4)	0.44643 (15)	0.1270 (13)
H10A	−0.0303	0.3816	0.4452	0.152*
C11	0.0111 (3)	0.2207 (4)	0.48895 (15)	0.1345 (15)
H11A	−0.0037	0.2532	0.5268	0.161*
H11B	−0.0400	0.1690	0.4763	0.161*
C12	0.0962 (3)	0.1465 (3)	0.49182 (11)	0.1062 (11)
H12A	0.0867	0.0783	0.5192	0.127*
C13	0.1786 (3)	0.2228 (3)	0.51154 (12)	0.1216 (13)
H13A	0.1668	0.2573	0.5494	0.146*
H13B	0.2333	0.1706	0.5138	0.146*
C14	0.1942 (3)	0.3267 (3)	0.46856 (11)	0.1081 (11)
H14A	0.2473	0.3770	0.4807	0.130*
C15	0.2122 (2)	0.2743 (2)	0.40942 (11)	0.0870 (7)
H15A	0.2678	0.2238	0.4104	0.104*
H15B	0.2224	0.3420	0.3826	0.104*
C16	0.1106 (4)	0.4060 (3)	0.46554 (14)	0.1354 (16)
H16A	0.1210	0.4730	0.4384	0.162*
H16B	0.0989	0.4425	0.5030	0.162*
C17	0.1172 (2)	0.0915 (2)	0.43319 (10)	0.0833 (7)
H17A	0.0665	0.0381	0.4213	0.100*
H17B	0.1728	0.0412	0.4354	0.100*
C18	0.15587 (18)	0.13589 (18)	0.33015 (9)	0.0714 (6)
H18A	0.2160	0.0949	0.3348	0.086*
C19	0.0894 (3)	0.0405 (2)	0.30786 (12)	0.1083 (11)
H19C	0.1093	0.0128	0.2705	0.162*
H19D	0.0288	0.0764	0.3049	0.162*
H19A	0.0876	−0.0290	0.3338	0.162*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.0373 (2)	0.0572 (2)	0.0757 (3)	0.000	0.00401 (17)	0.000
Cl1	0.0640 (3)	0.0912 (4)	0.0922 (4)	−0.0173 (3)	−0.0062 (3)	−0.0128 (3)
O1	0.0535 (8)	0.0748 (8)	0.0797 (9)	0.0163 (7)	0.0146 (7)	0.0132 (7)
N1	0.0719 (11)	0.0644 (9)	0.0532 (9)	0.0166 (8)	0.0069 (8)	0.0029 (7)
C1	0.0508 (10)	0.0633 (10)	0.0507 (10)	0.0077 (8)	0.0029 (8)	−0.0053 (8)
C2	0.0525 (9)	0.0646 (10)	0.0453 (9)	0.0103 (8)	0.0003 (7)	−0.0090 (8)
C3	0.0526 (11)	0.0935 (15)	0.0591 (11)	0.0137 (10)	0.0045 (9)	−0.0114 (11)
C4	0.0619 (12)	0.1086 (17)	0.0556 (12)	−0.0084 (12)	0.0152 (10)	−0.0094 (11)
C5	0.0841 (16)	0.0928 (16)	0.0614 (13)	−0.0038 (13)	0.0141 (12)	0.0079 (11)
C6	0.0718 (13)	0.0777 (13)	0.0667 (13)	0.0126 (11)	0.0070 (10)	0.0097 (10)
C7	0.0621 (11)	0.0715 (11)	0.0529 (10)	0.0202 (9)	0.0006 (9)	−0.0036 (9)
C8	0.0747 (12)	0.0550 (10)	0.0518 (10)	−0.0043 (9)	0.0029 (9)	0.0032 (8)
C9	0.0968 (18)	0.0992 (18)	0.0660 (14)	0.0251 (15)	0.0117 (13)	−0.0024 (12)
C10	0.150 (3)	0.146 (3)	0.085 (2)	0.042 (3)	0.036 (2)	−0.020 (2)
C11	0.167 (4)	0.162 (3)	0.0749 (19)	−0.034 (3)	0.055 (2)	−0.024 (2)
C12	0.162 (3)	0.0990 (18)	0.0575 (14)	−0.055 (2)	0.0025 (17)	0.0099 (13)
C13	0.184 (4)	0.120 (2)	0.0612 (15)	−0.062 (2)	−0.0143 (18)	0.0097 (14)
C14	0.165 (3)	0.0893 (18)	0.0700 (16)	−0.055 (2)	−0.0033 (18)	−0.0046 (14)
C15	0.1032 (18)	0.0898 (16)	0.0680 (14)	−0.0303 (15)	0.0001 (13)	0.0085 (12)
C16	0.251 (5)	0.0805 (18)	0.0749 (18)	−0.020 (3)	0.030 (2)	−0.0224 (14)
C17	0.117 (2)	0.0698 (13)	0.0630 (13)	−0.0202 (13)	−0.0064 (13)	0.0112 (10)
C18	0.0936 (16)	0.0595 (11)	0.0611 (12)	0.0133 (11)	0.0078 (11)	0.0043 (9)
C19	0.170 (3)	0.0786 (16)	0.0762 (16)	−0.0204 (18)	0.0176 (18)	−0.0210 (13)

Geometric parameters (Å, º)

Mn1—O1	2.0301 (14)	C10—C11	1.539 (5)
Mn1—O1^i	2.0301 (14)	C10—C16	1.553 (6)
Mn1—Cl1	2.3372 (7)	C10—H10A	0.9800
Mn1—Cl1^i	2.3372 (7)	C11—C12	1.467 (5)
O1—C1	1.310 (2)	C11—H11A	0.9700
N1—C7	1.284 (3)	C11—H11B	0.9700
N1—C18	1.465 (2)	C12—C17	1.515 (4)
N1—H1A	0.8600	C12—C13	1.517 (4)
C1—C6	1.397 (3)	C12—H12A	0.9800
C1—C2	1.419 (2)	C13—C14	1.515 (4)
C2—C3	1.411 (3)	C13—H13A	0.9700
C2—C7	1.416 (3)	C13—H13B	0.9700
C3—C4	1.360 (3)	C14—C16	1.480 (5)
C3—H3A	0.9300	C14—C15	1.507 (4)
C4—C5	1.377 (3)	C14—H14A	0.9800
C4—H4A	0.9300	C15—H15A	0.9700
C5—C6	1.370 (3)	C15—H15B	0.9700
C5—H5A	0.9300	C16—H16A	0.9700
C6—H6A	0.9300	C16—H16B	0.9700
C7—H7A	0.9300	C17—H17A	0.9700
C8—C9	1.503 (3)	C17—H17B	0.9700
C8—C15	1.529 (3)	C18—C19	1.497 (4)
C8—C17	1.534 (3)	C18—H18A	0.9800
C8—C18	1.542 (3)	C19—H19C	0.9600
C9—C10	1.538 (4)	C19—H19D	0.9600
C9—H9A	0.9700	C19—H19A	0.9600
C9—H9B	0.9700
O1—Mn1—O1^i	93.91 (9)	C12—C11—H11B	109.8
O1—Mn1—Cl1	109.87 (5)	C10—C11—H11B	109.8
O1^i—Mn1—Cl1	112.74 (5)	H11A—C11—H11B	108.3
O1—Mn1—Cl1^i	112.74 (5)	C11—C12—C17	109.8 (3)
O1^i—Mn1—Cl1^i	109.87 (5)	C11—C12—C13	112.1 (3)
Cl1—Mn1—Cl1^i	115.70 (4)	C17—C12—C13	109.0 (3)
C1—O1—Mn1	131.61 (13)	C11—C12—H12A	108.6
C7—N1—C18	125.59 (18)	C17—C12—H12A	108.6
C7—N1—H1A	117.2	C13—C12—H12A	108.6
C18—N1—H1A	117.2	C14—C13—C12	108.5 (2)
O1—C1—C6	122.78 (17)	C14—C13—H13A	110.0
O1—C1—C2	119.68 (17)	C12—C13—H13A	110.0
C6—C1—C2	117.54 (17)	C14—C13—H13B	110.0
C3—C2—C7	118.78 (18)	C12—C13—H13B	110.0
C3—C2—C1	119.62 (18)	H13A—C13—H13B	108.4
C7—C2—C1	121.59 (17)	C16—C14—C15	108.2 (3)
C4—C3—C2	120.8 (2)	C16—C14—C13	109.6 (3)
C4—C3—H3A	119.6	C15—C14—C13	110.5 (2)
C2—C3—H3A	119.6	C16—C14—H14A	109.5
C3—C4—C5	119.6 (2)	C15—C14—H14A	109.5
C3—C4—H4A	120.2	C13—C14—H14A	109.5
C5—C4—H4A	120.2	C14—C15—C8	111.4 (2)
C6—C5—C4	121.4 (2)	C14—C15—H15A	109.4
C6—C5—H5A	119.3	C8—C15—H15A	109.4
C4—C5—H5A	119.3	C14—C15—H15B	109.4
C5—C6—C1	121.1 (2)	C8—C15—H15B	109.4
C5—C6—H6A	119.5	H15A—C15—H15B	108.0
C1—C6—H6A	119.5	C14—C16—C10	110.8 (3)
N1—C7—C2	124.49 (19)	C14—C16—H16A	109.5
N1—C7—H7A	117.8	C10—C16—H16A	109.5
C2—C7—H7A	117.8	C14—C16—H16B	109.5
C9—C8—C15	109.3 (2)	C10—C16—H16B	109.5
C9—C8—C17	109.0 (2)	H16A—C16—H16B	108.1
C15—C8—C17	106.86 (18)	C12—C17—C8	110.39 (19)
C9—C8—C18	113.46 (18)	C12—C17—H17A	109.6
C15—C8—C18	109.15 (19)	C8—C17—H17A	109.6
C17—C8—C18	108.92 (16)	C12—C17—H17B	109.6
C8—C9—C10	110.0 (2)	C8—C17—H17B	109.6
C8—C9—H9A	109.7	H17A—C17—H17B	108.1
C10—C9—H9A	109.7	N1—C18—C19	108.2 (2)
C8—C9—H9B	109.7	N1—C18—C8	110.44 (15)
C10—C9—H9B	109.7	C19—C18—C8	115.9 (2)
H9A—C9—H9B	108.2	N1—C18—H18A	107.3
C9—C10—C11	108.3 (3)	C19—C18—H18A	107.3
C9—C10—C16	108.4 (3)	C8—C18—H18A	107.3
C11—C10—C16	108.9 (3)	C18—C19—H19C	109.5
C9—C10—H10A	110.4	C18—C19—H19D	109.5
C11—C10—H10A	110.4	H19C—C19—H19D	109.5
C16—C10—H10A	110.4	C18—C19—H19A	109.5
C12—C11—C10	109.3 (3)	H19C—C19—H19A	109.5
C12—C11—H11A	109.8	H19D—C19—H19A	109.5
C10—C11—H11A	109.8
O1^i—Mn1—O1—C1	168.6 (2)	C10—C11—C12—C13	59.6 (4)
Cl1—Mn1—O1—C1	−75.56 (18)	C11—C12—C13—C14	−61.0 (4)
Cl1^i—Mn1—O1—C1	55.10 (18)	C17—C12—C13—C14	60.8 (4)
Mn1—O1—C1—C6	−32.3 (3)	C12—C13—C14—C16	59.8 (4)
Mn1—O1—C1—C2	147.19 (15)	C12—C13—C14—C15	−59.3 (4)
O1—C1—C2—C3	−179.00 (18)	C16—C14—C15—C8	−60.6 (3)
C6—C1—C2—C3	0.5 (3)	C13—C14—C15—C8	59.4 (4)
O1—C1—C2—C7	0.2 (3)	C9—C8—C15—C14	59.7 (3)
C6—C1—C2—C7	179.68 (19)	C17—C8—C15—C14	−58.1 (3)
C7—C2—C3—C4	−179.2 (2)	C18—C8—C15—C14	−175.7 (2)
C1—C2—C3—C4	0.0 (3)	C15—C14—C16—C10	60.7 (3)
C2—C3—C4—C5	−0.4 (3)	C13—C14—C16—C10	−59.8 (3)
C3—C4—C5—C6	0.3 (4)	C9—C10—C16—C14	−60.1 (4)
C4—C5—C6—C1	0.3 (4)	C11—C10—C16—C14	57.6 (3)
O1—C1—C6—C5	178.8 (2)	C11—C12—C17—C8	60.3 (3)
C2—C1—C6—C5	−0.6 (3)	C13—C12—C17—C8	−62.9 (3)
C18—N1—C7—C2	178.61 (18)	C9—C8—C17—C12	−58.0 (3)
C3—C2—C7—N1	179.9 (2)	C15—C8—C17—C12	60.0 (3)
C1—C2—C7—N1	0.7 (3)	C18—C8—C17—C12	177.8 (3)
C15—C8—C9—C10	−58.1 (3)	C7—N1—C18—C19	−111.1 (3)
C17—C8—C9—C10	58.3 (3)	C7—N1—C18—C8	121.0 (2)
C18—C8—C9—C10	179.9 (2)	C9—C8—C18—N1	56.9 (3)
C8—C9—C10—C11	−60.0 (4)	C15—C8—C18—N1	−65.2 (2)
C8—C9—C10—C16	58.1 (4)	C17—C8—C18—N1	178.5 (2)
C9—C10—C11—C12	61.4 (4)	C9—C8—C18—C19	−66.6 (3)
C16—C10—C11—C12	−56.2 (4)	C15—C8—C18—C19	171.3 (2)
C10—C11—C12—C17	−61.8 (4)	C17—C8—C18—C19	54.9 (3)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.93	2.604 (2)	135