Di­aqua­(cyclo­hexane-1,1-diacetato-κ²O,O′)(phenanthroline-κ²N,N′)­manganese(II) trihydrate

In the crystal structure of the title compound, [Mn(C₁₀H₁₄O₄)(C₁₂H₈N₂)(H₂O)₂]·3H₂O, the Mn^II atom is in a distorted octahedral geometry, being coordinated by two N atoms of one 1,10-phenanthroline ligand, two O atoms from two carboxyl­ate groups of the chelating cyclo­hexane-1,1′-di­acetate dianion and two O atoms of two trans water mol­ecules. The complex mol­ecules are linked to form a three-dimensional network by hydrogen-bonding interactions between coordinated water mol­ecules, non-coordinated water mol­ecules and carboxyl­ate groups of neighbouring mol­ecules, and by aromatic π–π stacking interactions of the phenthroline rings.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.075
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.98 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Mn1    -   N2      ..       6.24 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

Diaqua(cyclohexane-1,1-diacetato-κ²O,O')(phenanthroline- κ²N,N')manganese(II) trihydrate

Crystal data

[Mn(C12H8N2)(C10H14O4)(H2O)2]·3H2O	F(000) = 1100.00
Mr = 523.44	Dx = 1.414 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 14069 reflections
a = 7.8763 (3) Å	θ = 2.3–27.4°
b = 25.0242 (7) Å	µ = 0.59 mm^−1
c = 12.7232 (3) Å	T = 297 K
β = 101.275 (1)°	Block, yellow
V = 2459.3 (1) Å^3	0.21 × 0.18 × 0.17 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	3284 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.045
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.801, Tmax = 0.905	k = −32→32
23941 measured reflections	l = −14→16
5611 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0003Fo^2 + σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.035	(Δ/σ)max < 0.001
wR(F^2) = 0.075	Δρmax = 0.45 e Å^−3
S = 1.02	Δρmin = −0.42 e Å^−3
5611 reflections	Extinction correction: Larson (1970)
308 parameters	Extinction coefficient: 11.4 (7)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Mn1	0.24115 (4)	0.33149 (1)	0.52464 (2)	0.03614 (8)
O1	0.3845 (2)	0.28331 (5)	0.6454 (1)	0.0459 (4)
O2	0.4695 (2)	0.22033 (6)	0.7633 (1)	0.0480 (4)
O3	0.1056 (2)	0.27555 (5)	0.4160 (1)	0.0436 (4)
O4	0.0319 (2)	0.20698 (5)	0.3091 (1)	0.0467 (4)
O5	0.4683 (2)	0.33129 (5)	0.4469 (1)	0.0439 (4)
O6	0.0181 (2)	0.33448 (5)	0.6079 (1)	0.0465 (4)
O7	0.7465 (2)	0.26586 (6)	0.5309 (1)	0.0661 (5)
O8	0.7989 (2)	0.20491 (6)	0.7141 (1)	0.0697 (6)
O9	0.6930 (2)	0.30735 (6)	0.8579 (1)	0.0702 (6)
N1	0.3556 (2)	0.40671 (6)	0.6129 (1)	0.0409 (5)
N2	0.1320 (2)	0.40264 (6)	0.4215 (1)	0.0410 (5)
C1	0.4674 (3)	0.40789 (9)	0.7061 (2)	0.0559 (7)
C2	0.5382 (4)	0.4551 (1)	0.7520 (2)	0.0737 (9)
C3	0.4928 (4)	0.5021 (1)	0.7013 (2)	0.073 (1)
C4	0.3752 (3)	0.50306 (8)	0.6029 (2)	0.0573 (8)
C5	0.3182 (4)	0.55073 (9)	0.5448 (3)	0.078 (1)
C6	0.2052 (4)	0.54872 (9)	0.4517 (3)	0.079 (1)
C7	0.1361 (3)	0.49916 (8)	0.4058 (2)	0.0588 (8)
C8	0.0178 (4)	0.4947 (1)	0.3085 (2)	0.077 (1)
C9	−0.0388 (4)	0.4462 (1)	0.2707 (2)	0.076 (1)
C10	0.0203 (3)	0.4007 (1)	0.3289 (2)	0.0574 (7)
C11	0.1899 (3)	0.45127 (7)	0.4603 (2)	0.0420 (6)
C12	0.3103 (3)	0.45317 (7)	0.5614 (2)	0.0420 (6)
C13	0.3639 (3)	0.23813 (7)	0.6845 (1)	0.0333 (5)
C14	0.2111 (3)	0.20394 (7)	0.6352 (1)	0.0333 (5)
C15	0.2431 (3)	0.16524 (7)	0.5460 (1)	0.0348 (5)
C16	0.3976 (3)	0.12878 (8)	0.5897 (1)	0.0521 (7)
C17	0.4172 (4)	0.08185 (9)	0.5171 (2)	0.081 (1)
C18	0.2520 (5)	0.04928 (9)	0.4889 (2)	0.099 (1)
C19	0.0988 (4)	0.08463 (9)	0.4403 (2)	0.0750 (9)
C20	0.0807 (3)	0.13036 (8)	0.5163 (2)	0.0500 (6)
C21	0.2815 (3)	0.19643 (7)	0.4480 (1)	0.0340 (5)
C22	0.1303 (3)	0.22845 (7)	0.3866 (1)	0.0333 (5)
H1	0.5008	0.3742	0.7438	0.067*
H2	0.6203	0.4547	0.8206	0.089*
H3	0.5418	0.5357	0.7333	0.092*
H4	0.3635	0.5854	0.5734	0.102*
H5	0.1672	0.5821	0.4140	0.104*
H6	−0.0231	0.5270	0.2680	0.097*
H7	−0.1212	0.4432	0.2025	0.091*
H8	−0.0225	0.3658	0.3008	0.069*
H9	0.1794	0.1825	0.6920	0.040*
H10	0.1158	0.2274	0.6054	0.039*
H11	0.5027	0.1500	0.5987	0.060*
H12	0.3836	0.1150	0.6587	0.061*
H13	0.4468	0.0954	0.4516	0.094*
H14	0.5094	0.0588	0.5533	0.093*
H15	0.2673	0.0221	0.4372	0.112*
H16	0.2287	0.0323	0.5531	0.112*
H17	0.1174	0.0992	0.3729	0.086*
H18	−0.0062	0.0633	0.4278	0.086*
H19	0.0553	0.1153	0.5817	0.058*
H20	−0.0150	0.1527	0.4823	0.058*
H21	0.3764	0.2208	0.4731	0.040*
H22	0.3160	0.1708	0.3989	0.041*
H23	0.5687	0.3105	0.4755	0.054*
H24	0.4537	0.3185	0.3775	0.054*
H25	0.0467	0.3226	0.6754	0.057*
H26	−0.0733	0.3136	0.5704	0.057*
H27	0.7526	0.2410	0.4809	0.079*
H28	0.7526	0.2490	0.5899	0.079*
H29	0.8861	0.2235	0.7513	0.083*
H30	0.7061	0.2125	0.7473	0.082*
H31	0.7939	0.3045	0.8272	0.083*
H32	0.6069	0.2826	0.8172	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.0396 (2)	0.0267 (1)	0.0420 (2)	0.0003 (1)	0.0075 (1)	0.0007 (1)
O1	0.044 (1)	0.0364 (7)	0.0525 (8)	−0.0049 (7)	−0.0016 (7)	0.0066 (6)
O2	0.042 (1)	0.0635 (9)	0.0337 (7)	−0.0056 (7)	−0.0052 (7)	0.0124 (6)
O3	0.042 (1)	0.0347 (7)	0.0497 (8)	0.0056 (6)	−0.0019 (7)	−0.0017 (6)
O4	0.044 (1)	0.0583 (8)	0.0333 (7)	−0.0009 (7)	−0.0027 (7)	−0.0091 (6)
O5	0.0443 (9)	0.0416 (7)	0.0477 (8)	−0.0017 (7)	0.0139 (7)	−0.0099 (6)
O6	0.048 (1)	0.0469 (8)	0.0464 (8)	0.0064 (7)	0.0130 (7)	0.0108 (6)
O7	0.046 (1)	0.093 (1)	0.0570 (9)	0.002 (1)	0.0063 (8)	−0.0035 (9)
O8	0.044 (1)	0.087 (1)	0.074 (1)	−0.0051 (9)	0.0013 (9)	−0.0219 (9)
O9	0.049 (1)	0.084 (1)	0.074 (1)	−0.0077 (9)	0.0033 (9)	−0.0201 (9)
N1	0.048 (1)	0.0354 (8)	0.0409 (9)	−0.0042 (8)	0.0135 (8)	−0.0019 (7)
N2	0.045 (1)	0.0401 (9)	0.0408 (9)	0.0078 (8)	0.0140 (8)	0.0023 (7)
C1	0.062 (2)	0.064 (1)	0.042 (1)	−0.012 (1)	0.009 (1)	−0.006 (1)
C2	0.076 (2)	0.089 (2)	0.058 (2)	−0.030 (2)	0.016 (1)	−0.028 (1)
C3	0.081 (2)	0.064 (2)	0.086 (2)	−0.035 (2)	0.043 (2)	−0.040 (1)
C4	0.066 (2)	0.038 (1)	0.082 (2)	−0.012 (1)	0.046 (2)	−0.014 (1)
C5	0.102 (3)	0.029 (1)	0.124 (2)	−0.008 (1)	0.071 (2)	−0.010 (1)
C6	0.109 (3)	0.033 (1)	0.119 (2)	0.019 (1)	0.076 (2)	0.023 (1)
C7	0.069 (2)	0.045 (1)	0.075 (2)	0.024 (1)	0.047 (1)	0.023 (1)
C8	0.084 (2)	0.084 (2)	0.073 (2)	0.049 (2)	0.041 (2)	0.041 (2)
C9	0.071 (2)	0.107 (2)	0.049 (1)	0.039 (2)	0.014 (1)	0.020 (1)
C10	0.053 (2)	0.072 (2)	0.047 (1)	0.018 (1)	0.008 (1)	0.001 (1)
C11	0.048 (1)	0.034 (1)	0.052 (1)	0.0108 (9)	0.030 (1)	0.0100 (9)
C12	0.049 (1)	0.031 (1)	0.055 (1)	−0.0013 (9)	0.030 (1)	−0.0039 (9)
C13	0.031 (1)	0.040 (1)	0.029 (1)	0.0018 (8)	0.0067 (9)	−0.0018 (8)
C14	0.032 (1)	0.0347 (9)	0.0328 (9)	0.0003 (8)	0.0060 (8)	0.0034 (8)
C15	0.037 (1)	0.0303 (9)	0.034 (1)	0.0022 (9)	0.0014 (9)	0.0012 (8)
C16	0.062 (2)	0.045 (1)	0.045 (1)	0.019 (1)	−0.001 (1)	0.0028 (9)
C17	0.108 (3)	0.054 (1)	0.072 (2)	0.044 (2)	−0.004 (2)	−0.005 (1)
C18	0.158 (3)	0.037 (1)	0.086 (2)	0.014 (2)	−0.012 (2)	−0.014 (1)
C19	0.108 (3)	0.044 (1)	0.063 (2)	−0.020 (1)	−0.007 (2)	−0.005 (1)
C20	0.059 (2)	0.041 (1)	0.045 (1)	−0.014 (1)	−0.003 (1)	0.0035 (9)
C21	0.033 (1)	0.035 (1)	0.033 (1)	0.0036 (9)	0.0044 (9)	−0.0035 (8)
C22	0.033 (1)	0.038 (1)	0.0291 (9)	−0.0022 (9)	0.0078 (9)	0.0025 (8)

Geometric parameters (Å, º)

Mn1—O1	2.101 (1)	C19—C20	1.522 (3)
Mn1—O3	2.105 (1)	C21—C22	1.518 (2)
Mn1—O5	2.207 (2)	O5—H23	0.96
Mn1—O6	2.224 (2)	O5—H24	0.92
Mn1—N1	2.285 (2)	O6—H25	0.89
Mn1—N2	2.278 (2)	O6—H26	0.94
O1—C13	1.258 (2)	O7—H27	0.90
O2—C13	1.252 (2)	O7—H28	0.85
O3—C22	1.263 (2)	O8—H29	0.88
O4—C22	1.250 (2)	O8—H30	0.93
N1—C1	1.332 (2)	O9—H31	0.95
N1—C12	1.348 (2)	O9—H32	0.99
N2—C10	1.326 (3)	C1—H1	0.98
N2—C11	1.358 (2)	C2—H2	0.98
C1—C2	1.386 (3)	C3—H3	0.98
C2—C3	1.355 (4)	C5—H4	0.98
C3—C4	1.404 (4)	C6—H5	0.98
C4—C5	1.429 (3)	C8—H6	0.98
C4—C12	1.412 (3)	C9—H7	0.98
C5—C6	1.337 (4)	C10—H8	0.98
C6—C7	1.432 (3)	C14—H9	0.97
C7—C8	1.401 (3)	C14—H10	0.97
C7—C11	1.408 (3)	C16—H11	0.97
C8—C9	1.348 (4)	C16—H12	0.97
C9—C10	1.388 (4)	C17—H13	0.97
C11—C12	1.442 (3)	C17—H14	0.97
C13—C14	1.509 (3)	C18—H15	0.97
C14—C15	1.549 (3)	C18—H16	0.97
C15—C16	1.536 (3)	C19—H17	0.97
C15—C20	1.534 (3)	C19—H18	0.97
C15—C21	1.551 (3)	C20—H19	0.97
C16—C17	1.520 (3)	C20—H20	0.97
C17—C18	1.518 (4)	C21—H21	0.97
C18—C19	1.526 (4)	C21—H22	0.97
O3—Mn1—O1	103.27 (5)	C18—C19—C20	110.1 (2)
O5—Mn1—O1	87.70 (5)	Mn1—O5—H23	120.7998
O6—Mn1—O1	91.86 (5)	Mn1—O5—H24	117.9140
N1—Mn1—O1	90.53 (5)	Mn1—O6—H25	111.7801
N2—Mn1—O1	163.41 (5)	Mn1—O6—H26	109.6342
Mn1—O1—C13	135.4 (1)	H24—O5—H23	96.5329
O5—Mn1—O3	93.19 (5)	H26—O6—H25	109.0152
O6—Mn1—O3	89.35 (5)	H28—O7—H27	106.2602
N1—Mn1—O3	166.19 (5)	H30—O8—H29	104.3199
N2—Mn1—O3	93.20 (5)	H32—O9—H31	106.2397
Mn1—O3—C22	136.7 (1)	N1—C1—H1	119.0086
O6—Mn1—O5	177.46 (5)	N2—C10—H8	118.5474
N1—Mn1—O5	86.90 (6)	H1—C1—C2	118.6156
N2—Mn1—O5	89.48 (6)	C1—C2—H2	120.4165
N1—Mn1—O6	90.60 (6)	H2—C2—C3	120.0720
N2—Mn1—O6	90.23 (6)	C2—C3—H3	120.0424
N2—Mn1—N1	72.99 (5)	H3—C3—C4	119.6191
Mn1—N1—C1	125.8 (1)	C4—C5—H4	119.4711
Mn1—N1—C12	115.5 (1)	H4—C5—C6	119.5376
Mn1—N2—C10	126.4 (1)	C5—C6—H5	119.2493
Mn1—N2—C11	115.4 (1)	H5—C6—C7	118.8923
O1—C13—C14	120.0 (1)	C7—C8—H6	119.4795
O1—C13—O2	121.3 (2)	C8—C9—H7	119.9976
O2—C13—C14	118.8 (2)	H6—C8—C9	120.2512
O3—C22—C21	119.4 (1)	C9—C10—H8	118.7761
O3—C22—O4	121.8 (2)	H7—C9—C10	120.3864
O4—C22—C21	118.8 (2)	C13—C14—H10	108.2065
C12—N1—C1	118.7 (2)	C13—C14—H9	107.7132
N1—C1—C2	122.4 (2)	H10—C14—C15	108.4206
N1—C12—C11	118.1 (2)	H9—C14—C15	107.6152
N1—C12—C4	122.6 (2)	H10—C14—H9	109.4601
C11—N2—C10	118.2 (2)	C15—C16—H11	108.4016
N2—C10—C9	122.7 (2)	C15—C16—H12	108.4530
N2—C11—C12	118.0 (2)	C15—C20—H20	108.6699
N2—C11—C7	122.4 (2)	C15—C20—H19	108.1222
C1—C2—C3	119.5 (2)	C15—C21—H21	108.1019
C2—C3—C4	120.3 (2)	C15—C21—H22	107.9410
C3—C4—C12	116.5 (2)	H11—C16—C17	107.9648
C3—C4—C5	124.1 (2)	H12—C16—C17	108.4893
C12—C4—C5	119.4 (2)	C16—C17—H13	108.7582
C4—C5—C6	121.0 (2)	C16—C17—H14	109.0202
C4—C12—C11	119.3 (2)	H12—C16—H11	109.4618
C5—C6—C7	121.9 (2)	H13—C17—C18	108.8615
C6—C7—C11	118.9 (2)	H14—C17—C18	108.7138
C6—C7—C8	124.3 (2)	C17—C18—H16	109.3031
C11—C7—C8	116.8 (2)	C17—C18—H15	108.8268
C7—C8—C9	120.3 (2)	H14—C17—H13	109.4602
C7—C11—C12	119.6 (2)	C18—C19—H17	109.3628
C8—C9—C10	119.6 (2)	H16—C18—C19	109.2431
C13—C14—C15	115.3 (2)	C18—C19—H18	109.1880
C14—C15—C21	111.1 (1)	H15—C18—C19	109.0036
C14—C15—C16	109.7 (1)	H16—C18—H15	109.4558
C14—C15—C20	106.8 (2)	C19—C20—H20	108.1559
C21—C15—C16	108.9 (2)	H17—C19—C20	109.1567
C20—C15—C16	108.4 (2)	C19—C20—H19	108.3184
C15—C16—C17	114.0 (2)	H18—C19—C20	109.5670
C21—C15—C20	111.8 (1)	H18—C19—H17	109.4575
C15—C20—C19	114.1 (2)	H20—C20—H19	109.4561
C15—C21—C22	115.0 (2)	H21—C21—C22	108.2712
C16—C17—C18	112.0 (3)	H22—C21—C22	107.9616
C17—C18—C19	111.0 (2)	H22—C21—H21	109.4666

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H23···O7	0.96	1.82	2.776 (2)	175
O5—H24···O2^i	0.93	1.77	2.671 (2)	163
O6—H25···O4^ii	0.90	1.88	2.744 (2)	162
O6—H26···O7^iii	0.94	1.85	2.769 (2)	165
O7—H27···O9^i	0.90	1.96	2.831 (2)	163
O7—H28···O8	0.85	1.90	2.748 (2)	170
O8—H29···O3^iv	0.89	2.44	3.201 (2)	144
O8—H29···O4^iv	0.89	2.13	2.970 (2)	157
O8—H30···O2	0.93	1.92	2.812 (2)	158
O9—H31···O4^iv	0.95	1.95	2.879 (2)	163
O9—H32···O1	0.99	2.52	3.318 (2)	138
O9—H32···O2	0.99	1.94	2.909 (2)	165

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