cis-Aqua­chloro­bis(1,10-phenanthroline-κ²N,N′)manganese(II) 4-formyl­benzoate trihydrate

The title compound, [MnCl(C₁₂H₈N₂)₂(H₂O)](C₈H₅O₃)·3H₂O, consists of cis-[Mn(phen)₂(H₂O)Cl]⁺ cations (phen = 1,10-phenanthroline), 4-formyl­benzoate anions and solvent water mol­ecules. The Mn^II atom is coordinated by four N atoms of two phen ligands, one Cl atom and one aqua ligand, forming a distorted octa­hedral geometry. A three-dimensional network is formed by O—H...O/Cl hydrogen bonds and π–π stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.109
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          5
              H2 O

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   0 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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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: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

cis-Aquachlorobis(1,10-phenanthroline-κ²N,N')manganese(II) 4-formylbenzoate trihydrate

Crystal data

[MnCl(C12H8N2)2(H2O)](C8H5O3)·3H2O)	Z = 2
Mr = 671.98	F(000) = 694
Triclinic, P1	Dx = 1.451 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.719 (2) Å	Cell parameters from 10995 reflections
b = 11.849 (2) Å	θ = 3.1–27.5°
c = 12.971 (3) Å	µ = 0.57 mm^−1
α = 103.33 (3)°	T = 295 K
β = 94.42 (3)°	Prism, colorless
γ = 104.23 (3)°	0.38 × 0.28 × 0.19 mm
V = 1538.2 (6) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	6947 independent reflections
Radiation source: fine-focus sealed tube	4816 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 10.000 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −12→13
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→15
Tmin = 0.812, Tmax = 0.899	l = −16→16
15102 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0413P)^2 + 0.6199P] where P = (Fo^2 + 2Fc^2)/3
6947 reflections	(Δ/σ)max = 0.001
430 parameters	Δρmax = 0.48 e Å^−3
12 restraints	Δρmin = −0.45 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	0.82448 (3)	0.61597 (3)	0.80237 (3)	0.03703 (11)
Cl1	0.95211 (6)	0.64255 (6)	0.97542 (5)	0.05277 (17)
O1W	0.95014 (17)	0.77574 (16)	0.78078 (15)	0.0520 (4)
H1W1	1.0207 (18)	0.815 (2)	0.8211 (19)	0.078*
H1W2	0.935 (3)	0.813 (2)	0.7341 (18)	0.078*
O2W	1.2195 (2)	0.8436 (2)	1.08825 (19)	0.0763 (6)
H2W1	1.198 (3)	0.884 (3)	1.144 (2)	0.114*
H2W2	1.158 (3)	0.780 (2)	1.061 (3)	0.114*
O3W	1.1885 (2)	0.9166 (2)	0.89310 (19)	0.0780 (6)
H3W1	1.191 (4)	0.906 (3)	0.9564 (14)	0.117*
H3W2	1.175 (4)	0.9859 (19)	0.896 (3)	0.117*
O4W	0.8801 (2)	0.8754 (2)	1.1291 (2)	0.0816 (7)
H4W1	0.9539 (19)	0.919 (3)	1.164 (3)	0.122*
H4W2	0.894 (3)	0.822 (3)	1.078 (2)	0.122*
O1	0.8743 (2)	1.02476 (19)	0.75171 (15)	0.0701 (6)
O2	0.9063 (2)	0.87847 (17)	0.62537 (14)	0.0607 (5)
O3	0.5102 (2)	1.1788 (2)	0.3554 (2)	0.0967 (8)
N1	0.74230 (18)	0.58146 (18)	0.62539 (15)	0.0426 (4)
N2	0.90322 (17)	0.46911 (16)	0.70927 (14)	0.0370 (4)
N3	0.64709 (18)	0.46607 (17)	0.81802 (15)	0.0415 (4)
N4	0.66784 (18)	0.70597 (17)	0.85613 (15)	0.0413 (4)
C1	0.6671 (2)	0.6384 (3)	0.5848 (2)	0.0549 (6)
H1	0.6385	0.6959	0.6314	0.066*
C2	0.6285 (3)	0.6158 (3)	0.4748 (3)	0.0677 (8)
H2	0.5751	0.6573	0.4490	0.081*
C3	0.6706 (3)	0.5322 (3)	0.4062 (2)	0.0636 (8)
H3	0.6453	0.5157	0.3328	0.076*
C4	0.7516 (2)	0.4710 (2)	0.44524 (19)	0.0487 (6)
C5	0.8026 (3)	0.3846 (3)	0.3779 (2)	0.0602 (7)
H5	0.7809	0.3667	0.3040	0.072*
C6	0.8808 (3)	0.3292 (3)	0.4191 (2)	0.0585 (7)
H6	0.9127	0.2737	0.3733	0.070*
C7	0.9166 (2)	0.3534 (2)	0.53216 (19)	0.0451 (6)
C8	0.9965 (2)	0.2960 (2)	0.5789 (2)	0.0540 (6)
H8	1.0290	0.2386	0.5360	0.065*
C9	1.0266 (3)	0.3244 (2)	0.6873 (2)	0.0552 (7)
H9	1.0781	0.2856	0.7191	0.066*
C10	0.9791 (2)	0.4123 (2)	0.7499 (2)	0.0449 (5)
H10	1.0017	0.4322	0.8238	0.054*
C11	0.8701 (2)	0.43908 (19)	0.60104 (17)	0.0365 (5)
C12	0.7853 (2)	0.4983 (2)	0.55686 (17)	0.0393 (5)
C13	0.6370 (3)	0.3494 (2)	0.8011 (2)	0.0516 (6)
H13	0.7083	0.3224	0.7814	0.062*
C14	0.5264 (3)	0.2652 (2)	0.8112 (2)	0.0614 (7)
H14	0.5242	0.1841	0.7978	0.074*
C15	0.4207 (3)	0.3027 (3)	0.8409 (2)	0.0575 (7)
H15	0.3453	0.2473	0.8473	0.069*
C16	0.4273 (2)	0.4260 (2)	0.86177 (18)	0.0455 (6)
C17	0.3224 (2)	0.4737 (3)	0.8956 (2)	0.0556 (7)
H17	0.2462	0.4220	0.9054	0.067*
C18	0.3325 (2)	0.5924 (3)	0.9134 (2)	0.0567 (7)
H18	0.2628	0.6210	0.9349	0.068*
C19	0.4482 (2)	0.6756 (2)	0.89999 (18)	0.0479 (6)
C20	0.4644 (3)	0.7999 (3)	0.9185 (2)	0.0590 (7)
H20	0.3969	0.8324	0.9395	0.071*
C21	0.5784 (3)	0.8731 (3)	0.9061 (2)	0.0585 (7)
H21	0.5896	0.9557	0.9186	0.070*
C22	0.6782 (3)	0.8226 (2)	0.8743 (2)	0.0499 (6)
H22	0.7557	0.8733	0.8655	0.060*
C23	0.5539 (2)	0.6319 (2)	0.86852 (16)	0.0387 (5)
C24	0.5435 (2)	0.5051 (2)	0.84878 (16)	0.0378 (5)
C25	0.8620 (2)	0.9662 (2)	0.6561 (2)	0.0471 (6)
C26	0.7874 (2)	1.0039 (2)	0.57242 (19)	0.0437 (5)
C27	0.7070 (3)	1.0785 (2)	0.6024 (2)	0.0539 (6)
H27	0.6985	1.1043	0.6742	0.065*
C28	0.6400 (3)	1.1142 (3)	0.5266 (2)	0.0585 (7)
H28	0.5855	1.1628	0.5473	0.070*
C29	0.6535 (3)	1.0782 (2)	0.4196 (2)	0.0552 (7)
C30	0.7347 (3)	1.0058 (3)	0.3894 (2)	0.0624 (7)
H30	0.7450	0.9822	0.3178	0.075*
C31	0.8009 (3)	0.9680 (2)	0.4658 (2)	0.0571 (7)
H31	0.8544	0.9183	0.4448	0.069*
C32	0.5834 (3)	1.1175 (3)	0.3387 (3)	0.0720 (9)
H32	0.5974	1.0924	0.2682	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.03974 (19)	0.0424 (2)	0.03120 (18)	0.01557 (15)	0.00662 (13)	0.00869 (14)
Cl1	0.0611 (4)	0.0599 (4)	0.0362 (3)	0.0149 (3)	−0.0018 (3)	0.0146 (3)
O1W	0.0545 (10)	0.0541 (11)	0.0473 (11)	0.0084 (9)	−0.0007 (8)	0.0223 (8)
O2W	0.0645 (13)	0.0831 (16)	0.0739 (16)	0.0223 (12)	0.0123 (11)	0.0027 (12)
O3W	0.0720 (13)	0.0771 (15)	0.0779 (16)	0.0205 (12)	−0.0059 (12)	0.0115 (12)
O4W	0.0689 (13)	0.0746 (16)	0.0918 (18)	0.0224 (12)	0.0031 (12)	0.0027 (12)
O1	0.0903 (15)	0.0737 (13)	0.0461 (12)	0.0386 (12)	−0.0034 (10)	0.0017 (10)
O2	0.0878 (13)	0.0656 (12)	0.0461 (11)	0.0453 (11)	0.0148 (9)	0.0204 (9)
O3	0.0837 (16)	0.114 (2)	0.116 (2)	0.0547 (16)	0.0011 (14)	0.0502 (17)
N1	0.0443 (10)	0.0490 (11)	0.0358 (10)	0.0148 (9)	0.0021 (8)	0.0126 (9)
N2	0.0401 (10)	0.0408 (10)	0.0326 (10)	0.0165 (8)	0.0076 (7)	0.0078 (8)
N3	0.0443 (10)	0.0464 (11)	0.0354 (10)	0.0156 (9)	0.0085 (8)	0.0095 (8)
N4	0.0442 (11)	0.0456 (11)	0.0355 (10)	0.0185 (9)	0.0060 (8)	0.0067 (8)
C1	0.0509 (14)	0.0631 (16)	0.0576 (17)	0.0235 (13)	−0.0007 (12)	0.0230 (13)
C2	0.0595 (17)	0.089 (2)	0.0617 (19)	0.0222 (16)	−0.0100 (14)	0.0372 (17)
C3	0.0616 (17)	0.087 (2)	0.0368 (14)	0.0063 (16)	−0.0077 (12)	0.0250 (14)
C4	0.0457 (13)	0.0581 (15)	0.0343 (13)	−0.0015 (12)	0.0008 (10)	0.0144 (11)
C5	0.0656 (17)	0.0721 (18)	0.0282 (13)	−0.0004 (15)	0.0075 (11)	0.0046 (12)
C6	0.0612 (16)	0.0606 (16)	0.0408 (15)	0.0047 (14)	0.0174 (12)	−0.0028 (12)
C7	0.0424 (12)	0.0405 (12)	0.0463 (14)	0.0035 (11)	0.0163 (10)	0.0043 (10)
C8	0.0513 (14)	0.0449 (14)	0.0653 (18)	0.0189 (12)	0.0184 (13)	0.0035 (12)
C9	0.0518 (15)	0.0494 (15)	0.0708 (19)	0.0230 (13)	0.0096 (13)	0.0180 (13)
C10	0.0457 (13)	0.0494 (14)	0.0471 (14)	0.0222 (11)	0.0086 (10)	0.0166 (11)
C11	0.0353 (11)	0.0391 (12)	0.0339 (12)	0.0071 (10)	0.0094 (9)	0.0088 (9)
C12	0.0378 (11)	0.0447 (12)	0.0314 (11)	0.0029 (10)	0.0041 (9)	0.0112 (9)
C13	0.0565 (15)	0.0431 (14)	0.0561 (16)	0.0164 (12)	0.0133 (12)	0.0101 (11)
C14	0.0673 (18)	0.0452 (15)	0.0682 (19)	0.0076 (14)	0.0148 (14)	0.0140 (13)
C15	0.0530 (15)	0.0621 (17)	0.0498 (16)	−0.0015 (13)	0.0051 (12)	0.0190 (13)
C16	0.0407 (12)	0.0645 (16)	0.0292 (12)	0.0083 (12)	0.0023 (9)	0.0152 (11)
C17	0.0411 (13)	0.084 (2)	0.0383 (14)	0.0091 (14)	0.0063 (10)	0.0183 (13)
C18	0.0398 (13)	0.090 (2)	0.0415 (14)	0.0234 (14)	0.0096 (10)	0.0122 (14)
C19	0.0447 (13)	0.0704 (17)	0.0319 (12)	0.0277 (13)	0.0048 (9)	0.0070 (11)
C20	0.0580 (16)	0.0723 (19)	0.0528 (16)	0.0407 (15)	0.0090 (12)	0.0035 (13)
C21	0.0660 (17)	0.0542 (16)	0.0580 (17)	0.0333 (14)	0.0018 (13)	0.0038 (13)
C22	0.0548 (15)	0.0434 (13)	0.0513 (15)	0.0206 (12)	0.0070 (11)	0.0042 (11)
C23	0.0381 (11)	0.0542 (14)	0.0257 (11)	0.0179 (11)	0.0036 (8)	0.0084 (9)
C24	0.0395 (11)	0.0510 (13)	0.0238 (10)	0.0145 (10)	0.0019 (8)	0.0102 (9)
C25	0.0539 (14)	0.0465 (14)	0.0436 (14)	0.0172 (12)	0.0086 (11)	0.0125 (11)
C26	0.0471 (13)	0.0380 (12)	0.0468 (14)	0.0117 (11)	0.0050 (10)	0.0129 (10)
C27	0.0571 (15)	0.0545 (15)	0.0540 (16)	0.0225 (13)	0.0113 (12)	0.0127 (12)
C28	0.0525 (15)	0.0594 (17)	0.0700 (19)	0.0252 (13)	0.0084 (13)	0.0187 (14)
C29	0.0500 (14)	0.0534 (15)	0.0643 (18)	0.0125 (13)	−0.0014 (12)	0.0238 (13)
C30	0.0796 (19)	0.0668 (18)	0.0471 (16)	0.0304 (16)	0.0058 (13)	0.0169 (13)
C31	0.0716 (17)	0.0603 (16)	0.0492 (16)	0.0340 (14)	0.0094 (13)	0.0156 (13)
C32	0.0684 (19)	0.075 (2)	0.077 (2)	0.0189 (17)	−0.0047 (16)	0.0321 (17)

Geometric parameters (Å, º)

Mn1—O1W	2.1272 (18)	C8—C9	1.361 (4)
Mn1—N2	2.2602 (19)	C8—H8	0.9300
Mn1—N4	2.2717 (19)	C9—C10	1.392 (3)
Mn1—N1	2.300 (2)	C9—H9	0.9300
Mn1—N3	2.319 (2)	C10—H10	0.9300
Mn1—Cl1	2.4491 (10)	C11—C12	1.438 (3)
O1W—H1W1	0.85 (2)	C13—C14	1.386 (4)
O1W—H1W2	0.86 (2)	C13—H13	0.9300
O2W—H2W1	0.85 (3)	C14—C15	1.366 (4)
O2W—H2W2	0.85 (3)	C14—H14	0.9300
O3W—H3W1	0.86 (3)	C15—C16	1.406 (4)
O3W—H3W2	0.86 (3)	C15—H15	0.9300
O4W—H4W1	0.86 (3)	C16—C24	1.410 (3)
O4W—H4W2	0.85 (3)	C16—C17	1.431 (4)
O1—C25	1.253 (3)	C17—C18	1.348 (4)
O2—C25	1.243 (3)	C17—H17	0.9300
O3—C32	1.194 (4)	C18—C19	1.432 (4)
N1—C1	1.322 (3)	C18—H18	0.9300
N1—C12	1.362 (3)	C19—C20	1.400 (4)
N2—C10	1.326 (3)	C19—C23	1.407 (3)
N2—C11	1.362 (3)	C20—C21	1.358 (4)
N3—C13	1.324 (3)	C20—H20	0.9300
N3—C24	1.357 (3)	C21—C22	1.394 (4)
N4—C22	1.322 (3)	C21—H21	0.9300
N4—C23	1.363 (3)	C22—H22	0.9300
C1—C2	1.399 (4)	C23—C24	1.439 (3)
C1—H1	0.9300	C25—C26	1.510 (3)
C2—C3	1.362 (4)	C26—C31	1.380 (4)
C2—H2	0.9300	C26—C27	1.394 (3)
C3—C4	1.396 (4)	C27—C28	1.377 (4)
C3—H3	0.9300	C27—H27	0.9300
C4—C12	1.406 (3)	C28—C29	1.384 (4)
C4—C5	1.431 (4)	C28—H28	0.9300
C5—C6	1.335 (4)	C29—C30	1.382 (4)
C5—H5	0.9300	C29—C32	1.469 (4)
C6—C7	1.430 (4)	C30—C31	1.392 (4)
C6—H6	0.9300	C30—H30	0.9300
C7—C8	1.400 (4)	C31—H31	0.9300
C7—C11	1.406 (3)	C32—H32	0.9300
O1W—Mn1—N2	102.95 (7)	C7—C11—C12	119.5 (2)
O1W—Mn1—N4	94.20 (8)	N1—C12—C4	122.2 (2)
N2—Mn1—N4	155.69 (7)	N1—C12—C11	118.33 (19)
O1W—Mn1—N1	85.04 (8)	C4—C12—C11	119.5 (2)
N2—Mn1—N1	73.46 (7)	N3—C13—C14	123.8 (2)
N4—Mn1—N1	91.26 (7)	N3—C13—H13	118.1
O1W—Mn1—N3	165.37 (7)	C14—C13—H13	118.1
N2—Mn1—N3	87.89 (7)	C15—C14—C13	119.2 (3)
N4—Mn1—N3	72.66 (7)	C15—C14—H14	120.4
N1—Mn1—N3	88.76 (8)	C13—C14—H14	120.4
O1W—Mn1—Cl1	91.04 (6)	C14—C15—C16	119.2 (2)
N2—Mn1—Cl1	96.37 (6)	C14—C15—H15	120.4
N4—Mn1—Cl1	100.46 (6)	C16—C15—H15	120.4
N1—Mn1—Cl1	167.89 (5)	C15—C16—C24	117.7 (2)
N3—Mn1—Cl1	97.57 (6)	C15—C16—C17	123.0 (2)
Mn1—O1W—H1W1	124.4 (17)	C24—C16—C17	119.3 (2)
Mn1—O1W—H1W2	126.0 (18)	C18—C17—C16	121.0 (2)
H1W1—O1W—H1W2	109.4 (15)	C18—C17—H17	119.5
H2W1—O2W—H2W2	108.5 (16)	C16—C17—H17	119.5
H3W1—O3W—H3W2	107.8 (16)	C17—C18—C19	121.5 (2)
H4W1—O4W—H4W2	107.8 (16)	C17—C18—H18	119.3
C1—N1—C12	118.5 (2)	C19—C18—H18	119.3
C1—N1—Mn1	127.16 (18)	C20—C19—C23	117.2 (2)
C12—N1—Mn1	114.23 (15)	C20—C19—C18	123.8 (2)
C10—N2—C11	118.03 (19)	C23—C19—C18	118.9 (2)
C10—N2—Mn1	126.29 (16)	C21—C20—C19	120.2 (2)
C11—N2—Mn1	115.67 (14)	C21—C20—H20	119.9
C13—N3—C24	117.7 (2)	C19—C20—H20	119.9
C13—N3—Mn1	127.46 (16)	C20—C21—C22	119.1 (3)
C24—N3—Mn1	114.82 (15)	C20—C21—H21	120.5
C22—N4—C23	118.3 (2)	C22—C21—H21	120.5
C22—N4—Mn1	125.34 (16)	N4—C22—C21	123.0 (3)
C23—N4—Mn1	116.33 (15)	N4—C22—H22	118.5
N1—C1—C2	122.9 (3)	C21—C22—H22	118.5
N1—C1—H1	118.6	N4—C23—C19	122.2 (2)
C2—C1—H1	118.6	N4—C23—C24	117.97 (19)
C3—C2—C1	118.8 (3)	C19—C23—C24	119.8 (2)
C3—C2—H2	120.6	N3—C24—C16	122.4 (2)
C1—C2—H2	120.6	N3—C24—C23	118.2 (2)
C2—C3—C4	120.4 (3)	C16—C24—C23	119.4 (2)
C2—C3—H3	119.8	O2—C25—O1	124.4 (2)
C4—C3—H3	119.8	O2—C25—C26	117.7 (2)
C3—C4—C12	117.3 (3)	O1—C25—C26	117.9 (2)
C3—C4—C5	123.4 (2)	C31—C26—C27	119.1 (2)
C12—C4—C5	119.2 (2)	C31—C26—C25	120.5 (2)
C6—C5—C4	121.2 (2)	C27—C26—C25	120.3 (2)
C6—C5—H5	119.4	C28—C27—C26	120.5 (3)
C4—C5—H5	119.4	C28—C27—H27	119.7
C5—C6—C7	121.5 (2)	C26—C27—H27	119.7
C5—C6—H6	119.2	C27—C28—C29	120.4 (3)
C7—C6—H6	119.2	C27—C28—H28	119.8
C8—C7—C11	117.6 (2)	C29—C28—H28	119.8
C8—C7—C6	123.4 (2)	C30—C29—C28	119.5 (3)
C11—C7—C6	119.1 (2)	C30—C29—C32	120.1 (3)
C9—C8—C7	119.8 (2)	C28—C29—C32	120.4 (3)
C9—C8—H8	120.1	C29—C30—C31	120.3 (3)
C7—C8—H8	120.1	C29—C30—H30	119.9
C8—C9—C10	119.2 (2)	C31—C30—H30	119.9
C8—C9—H9	120.4	C26—C31—C30	120.2 (3)
C10—C9—H9	120.4	C26—C31—H31	119.9
N2—C10—C9	123.2 (2)	C30—C31—H31	119.9
N2—C10—H10	118.4	O3—C32—C29	125.8 (3)
C9—C10—H10	118.4	O3—C32—H32	117.1
N2—C11—C7	122.3 (2)	C29—C32—H32	117.1
N2—C11—C12	118.20 (19)
O1W—Mn1—N1—C1	−73.0 (2)	C1—N1—C12—C4	−0.4 (3)
N2—Mn1—N1—C1	−178.1 (2)	Mn1—N1—C12—C4	−176.12 (16)
N4—Mn1—N1—C1	21.1 (2)	C1—N1—C12—C11	178.3 (2)
N3—Mn1—N1—C1	93.7 (2)	Mn1—N1—C12—C11	2.6 (2)
Cl1—Mn1—N1—C1	−144.5 (2)	C3—C4—C12—N1	−0.4 (3)
O1W—Mn1—N1—C12	102.27 (16)	C5—C4—C12—N1	178.6 (2)
N2—Mn1—N1—C12	−2.83 (14)	C3—C4—C12—C11	−179.1 (2)
N4—Mn1—N1—C12	−163.63 (15)	C5—C4—C12—C11	0.0 (3)
N3—Mn1—N1—C12	−91.00 (15)	N2—C11—C12—N1	0.0 (3)
Cl1—Mn1—N1—C12	30.8 (4)	C7—C11—C12—N1	−179.62 (19)
O1W—Mn1—N2—C10	100.86 (19)	N2—C11—C12—C4	178.70 (19)
N4—Mn1—N2—C10	−125.4 (2)	C7—C11—C12—C4	−0.9 (3)
N1—Mn1—N2—C10	−178.39 (19)	C24—N3—C13—C14	1.2 (4)
N3—Mn1—N2—C10	−89.06 (19)	Mn1—N3—C13—C14	−179.2 (2)
Cl1—Mn1—N2—C10	8.32 (18)	N3—C13—C14—C15	−0.5 (4)
O1W—Mn1—N2—C11	−77.89 (15)	C13—C14—C15—C16	−0.7 (4)
N4—Mn1—N2—C11	55.9 (2)	C14—C15—C16—C24	1.1 (4)
N1—Mn1—N2—C11	2.86 (14)	C14—C15—C16—C17	−178.6 (2)
N3—Mn1—N2—C11	92.19 (15)	C15—C16—C17—C18	−179.2 (2)
Cl1—Mn1—N2—C11	−170.43 (14)	C24—C16—C17—C18	1.1 (4)
O1W—Mn1—N3—C13	154.2 (3)	C16—C17—C18—C19	−0.4 (4)
N2—Mn1—N3—C13	15.9 (2)	C17—C18—C19—C20	−179.3 (2)
N4—Mn1—N3—C13	−178.9 (2)	C17—C18—C19—C23	−0.7 (4)
N1—Mn1—N3—C13	89.4 (2)	C23—C19—C20—C21	0.0 (4)
Cl1—Mn1—N3—C13	−80.3 (2)	C18—C19—C20—C21	178.6 (3)
O1W—Mn1—N3—C24	−26.2 (4)	C19—C20—C21—C22	0.3 (4)
N2—Mn1—N3—C24	−164.57 (15)	C23—N4—C22—C21	0.4 (4)
N4—Mn1—N3—C24	0.63 (14)	Mn1—N4—C22—C21	179.26 (19)
N1—Mn1—N3—C24	−91.08 (16)	C20—C21—C22—N4	−0.5 (4)
Cl1—Mn1—N3—C24	99.28 (15)	C22—N4—C23—C19	−0.2 (3)
O1W—Mn1—N4—C22	−6.4 (2)	Mn1—N4—C23—C19	−179.10 (16)
N2—Mn1—N4—C22	−141.5 (2)	C22—N4—C23—C24	−179.9 (2)
N1—Mn1—N4—C22	−91.5 (2)	Mn1—N4—C23—C24	1.2 (2)
N3—Mn1—N4—C22	−179.8 (2)	C20—C19—C23—N4	0.0 (3)
Cl1—Mn1—N4—C22	85.4 (2)	C18—C19—C23—N4	−178.7 (2)
O1W—Mn1—N4—C23	172.48 (15)	C20—C19—C23—C24	179.7 (2)
N2—Mn1—N4—C23	37.4 (3)	C18—C19—C23—C24	1.0 (3)
N1—Mn1—N4—C23	87.36 (16)	C13—N3—C24—C16	−0.7 (3)
N3—Mn1—N4—C23	−0.94 (14)	Mn1—N3—C24—C16	179.70 (16)
Cl1—Mn1—N4—C23	−95.68 (15)	C13—N3—C24—C23	179.3 (2)
C12—N1—C1—C2	0.8 (4)	Mn1—N3—C24—C23	−0.3 (2)
Mn1—N1—C1—C2	175.88 (19)	C15—C16—C24—N3	−0.4 (3)
N1—C1—C2—C3	−0.3 (4)	C17—C16—C24—N3	179.3 (2)
C1—C2—C3—C4	−0.5 (4)	C15—C16—C24—C23	179.5 (2)
C2—C3—C4—C12	0.9 (4)	C17—C16—C24—C23	−0.7 (3)
C2—C3—C4—C5	−178.1 (3)	N4—C23—C24—N3	−0.6 (3)
C3—C4—C5—C6	179.4 (3)	C19—C23—C24—N3	179.67 (19)
C12—C4—C5—C6	0.4 (4)	N4—C23—C24—C16	179.44 (19)
C4—C5—C6—C7	0.2 (4)	C19—C23—C24—C16	−0.3 (3)
C5—C6—C7—C8	178.9 (2)	O2—C25—C26—C31	−19.0 (4)
C5—C6—C7—C11	−1.1 (4)	O1—C25—C26—C31	161.5 (2)
C11—C7—C8—C9	−0.2 (3)	O2—C25—C26—C27	162.9 (2)
C6—C7—C8—C9	179.8 (2)	O1—C25—C26—C27	−16.6 (4)
C7—C8—C9—C10	−1.3 (4)	C31—C26—C27—C28	1.1 (4)
C11—N2—C10—C9	0.3 (3)	C25—C26—C27—C28	179.2 (2)
Mn1—N2—C10—C9	−178.45 (17)	C26—C27—C28—C29	−1.1 (4)
C8—C9—C10—N2	1.3 (4)	C27—C28—C29—C30	0.1 (4)
C10—N2—C11—C7	−1.9 (3)	C27—C28—C29—C32	−179.2 (3)
Mn1—N2—C11—C7	176.98 (16)	C28—C29—C30—C31	0.9 (4)
C10—N2—C11—C12	178.52 (19)	C32—C29—C30—C31	−179.8 (3)
Mn1—N2—C11—C12	−2.6 (2)	C27—C26—C31—C30	−0.1 (4)
C8—C7—C11—N2	1.9 (3)	C25—C26—C31—C30	−178.2 (2)
C6—C7—C11—N2	−178.1 (2)	C29—C30—C31—C26	−0.9 (4)
C8—C7—C11—C12	−178.6 (2)	C30—C29—C32—O3	179.2 (3)
C6—C7—C11—C12	1.5 (3)	C28—C29—C32—O3	−1.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3W	0.85 (2)	1.93 (3)	2.765 (3)	170 (3)
O1W—H1W2···O2	0.86 (2)	1.80 (2)	2.652 (2)	174 (3)
O2W—H2W1···O1^i	0.85 (3)	1.87 (3)	2.711 (3)	169 (4)
O2W—H2W2···Cl1	0.85 (3)	2.40 (3)	3.228 (3)	164 (4)
O3W—H3W1···O2W	0.86 (3)	2.04 (3)	2.878 (4)	164 (3)
O3W—H3W2···O4W^i	0.86 (3)	1.96 (3)	2.807 (4)	167 (4)
O4W—H4W1···O1^i	0.86 (3)	1.94 (3)	2.779 (3)	164 (4)
O4W—H4W2···Cl1	0.85 (3)	2.48 (3)	3.306 (3)	162 (4)

Symmetry code: (i) −x+2, −y+2, −z+2.