Aqua­(hippurato)bis­(1,10-phenanthroline)manganese(II) perchlorate trihydrate

In the cation of the title compound, [Mn(C₉H₇NO₃)(C₁₂H₁₀N₂)₂(H₂O)]ClO₄·3H₂O, the Mn^II atom is coordinated by two O atoms, one from a hippurate ligand and the other from a coordinated water mol­ecule, and four N atoms from two 1,10-phenanthroline ligands. In the crystal structure, the cations and water mol­ecules are linked by intra- and inter­molecular hydrogen bonds, forming R₆⁴(12) rings; these rings are further connected by inter­molecular hydrogen bonds and C—H...π inter­actions into a three-dimensional supra­molecular framework.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.049
• wR factor = 0.142
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C21
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      33.00 Perc.

   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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXS97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.

Aqua(hippurato)bis(1,10-phenanthroline)manganese(II) perchlorate trihydrate

Crystal data

[Mn(C9H7NO3)(C12H10N2)2(H2O)]ClO4·3H2O	F(000) = 1580
Mr = 765.03	Dx = 1.436 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3200 reflections
a = 14.1328 (12) Å	θ = 1.0–27.5°
b = 16.0110 (14) Å	µ = 0.52 mm^−1
c = 16.8357 (14) Å	T = 298 K
β = 111.774 (1)°	Needle, yellow
V = 3537.8 (5) Å^3	0.45 × 0.24 × 0.22 mm
Z = 4

Data collection

Bruker SMART CCD APEXII diffractometer	8777 independent reflections
Radiation source: fine-focus sealed tube	4663 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 8.35 pixels mm^-1	θmax = 28.6°, θmin = 2.4°
ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −21→17
Tmin = 0.856, Tmax = 0.885	l = −22→22
25123 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0595P)^2 + 0.3436P] where P = (Fo^2 + 2Fc^2)/3
8777 reflections	(Δ/σ)max = 0.001
497 parameters	Δρmax = 0.36 e Å^−3
80 restraints	Δρmin = −0.39 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	Occ. (<1)
Mn1	0.34418 (3)	0.73675 (2)	0.46202 (2)	0.05019 (14)
Cl1	0.23885 (7)	0.97709 (6)	0.71820 (5)	0.0776 (3)
O1	0.22911 (13)	0.65692 (11)	0.47224 (12)	0.0583 (5)
N1	0.47690 (16)	0.83000 (14)	0.49398 (14)	0.0570 (6)
N4	0.30066 (18)	0.75629 (14)	0.31814 (14)	0.0582 (6)
N2	0.4042 (2)	0.76001 (15)	0.60636 (14)	0.0628 (6)
N5	0.13892 (16)	0.46531 (13)	0.53121 (13)	0.0540 (6)
H5A	0.1622	0.4472	0.5830	0.065*
C26	0.1429 (2)	0.55307 (17)	0.51593 (19)	0.0583 (7)
H26B	0.1448	0.5830	0.5666	0.070*
H26A	0.0806	0.5689	0.4695	0.070*
C24	0.2319 (2)	0.81775 (18)	0.28318 (17)	0.0571 (7)
C25	0.2320 (2)	0.58129 (16)	0.49389 (16)	0.0493 (6)
C12	0.51674 (19)	0.85573 (17)	0.57719 (17)	0.0548 (7)
O2	0.30107 (15)	0.53167 (12)	0.49865 (15)	0.0755 (6)
O1W	0.42924 (16)	0.62822 (12)	0.45936 (16)	0.0837 (7)
C11	0.4788 (2)	0.81806 (17)	0.63656 (16)	0.0556 (7)
C23	0.19232 (19)	0.86251 (17)	0.33828 (18)	0.0573 (7)
N3	0.22755 (16)	0.84083 (13)	0.42207 (14)	0.0544 (5)
C28	0.1022 (2)	0.32130 (16)	0.49154 (16)	0.0507 (6)
C4	0.5937 (2)	0.9167 (2)	0.6060 (2)	0.0706 (8)
C7	0.5210 (2)	0.8407 (2)	0.72346 (19)	0.0716 (9)
O3	0.06351 (18)	0.43420 (13)	0.39251 (13)	0.0818 (7)
C27	0.09991 (19)	0.41106 (17)	0.46715 (17)	0.0531 (7)
C9	0.4146 (4)	0.7384 (3)	0.7500 (2)	0.0972 (12)
H9	0.3929	0.7086	0.7875	0.117*
C33	0.0231 (3)	0.2695 (2)	0.44476 (19)	0.0708 (9)
H33	−0.0318	0.2909	0.3992	0.085*
C16	0.1981 (3)	0.8394 (3)	0.1959 (2)	0.0818 (10)
C8	0.4859 (3)	0.7982 (3)	0.7794 (2)	0.0934 (12)
H8	0.5119	0.8114	0.8374	0.112*
C14	0.3064 (4)	0.7317 (3)	0.1798 (3)	0.1023 (13)
H14	0.3328	0.7010	0.1459	0.123*
C29	0.1829 (2)	0.28810 (19)	0.55800 (19)	0.0665 (8)
H29	0.2367	0.3224	0.5899	0.080*
C5	0.6309 (3)	0.9404 (3)	0.6937 (3)	0.0951 (12)
H5	0.6804	0.9818	0.7127	0.114*
C13	0.3368 (3)	0.7146 (2)	0.2674 (2)	0.0786 (9)
H13	0.3841	0.6723	0.2909	0.094*
C22	0.1904 (3)	0.8813 (2)	0.4730 (2)	0.0779 (9)
H22	0.2145	0.8673	0.5307	0.094*
C19	0.1195 (2)	0.9254 (2)	0.3046 (2)	0.0797 (10)
C1	0.5147 (2)	0.8635 (2)	0.4396 (2)	0.0723 (9)
H1	0.4884	0.8459	0.3830	0.087*
C10	0.3737 (3)	0.7216 (2)	0.6625 (2)	0.0855 (10)
H10	0.3226	0.6816	0.6426	0.103*
O4W	0.57351 (18)	0.68194 (16)	0.27317 (15)	0.0989 (8)
O3W	−0.0530 (2)	0.35671 (15)	0.24267 (14)	0.1009 (8)
O2W	0.59156 (17)	0.60493 (16)	0.42477 (17)	0.1032 (9)
C30	0.1847 (3)	0.2044 (2)	0.5778 (2)	0.0903 (11)
H30	0.2400	0.1824	0.6225	0.108*
C2	0.5914 (3)	0.9236 (2)	0.4629 (2)	0.0844 (10)
H2	0.6157	0.9454	0.4229	0.101*
C18	0.0875 (3)	0.9445 (3)	0.2150 (3)	0.1182 (16)
H18	0.0394	0.9863	0.1919	0.142*
C3	0.6298 (2)	0.9495 (2)	0.5455 (3)	0.0884 (11)
H3	0.6809	0.9898	0.5622	0.106*
C32	0.0255 (3)	0.1858 (2)	0.4657 (2)	0.0985 (13)
H32	−0.0279	0.1509	0.4345	0.118*
C15	0.2388 (4)	0.7929 (3)	0.1454 (2)	0.1059 (14)
H15	0.2187	0.8048	0.0874	0.127*
C21	0.1174 (3)	0.9435 (2)	0.4440 (3)	0.1084 (14)
H21	0.0926	0.9696	0.4817	0.130*
C20	0.0824 (3)	0.9660 (2)	0.3608 (3)	0.1045 (13)
H20	0.0340	1.0082	0.3410	0.125*
C17	0.1249 (4)	0.9040 (3)	0.1642 (3)	0.1128 (16)
H17	0.1026	0.9182	0.1067	0.135*
C6	0.5966 (3)	0.9047 (3)	0.7495 (2)	0.0978 (12)
H6	0.6224	0.9218	0.8063	0.117*
C31	0.1063 (4)	0.1543 (2)	0.5324 (3)	0.1073 (13)
H31	0.1073	0.0981	0.5465	0.129*
O5A	0.2374 (6)	1.0552 (3)	0.7579 (3)	0.161 (3)	0.731 (9)
O4A	0.1418 (3)	0.9594 (4)	0.6578 (3)	0.129 (2)	0.731 (9)
O6A	0.3052 (4)	0.9858 (5)	0.6723 (3)	0.141 (2)	0.731 (9)
O7A	0.2740 (6)	0.9165 (3)	0.7793 (3)	0.136 (2)	0.731 (9)
O4B	0.2660 (14)	1.0247 (9)	0.6654 (9)	0.151 (7)	0.269 (9)
O5B	0.1838 (12)	1.0118 (13)	0.7621 (10)	0.192 (9)	0.269 (9)
O6B	0.1933 (14)	0.8999 (8)	0.6835 (8)	0.141 (6)	0.269 (9)
O7B	0.3311 (8)	0.9493 (10)	0.7845 (7)	0.110 (5)	0.269 (9)
H1B	0.4019	0.5834	0.4738	0.164*
H1A	0.4847	0.6113	0.4497	0.164*
H2B	0.6309	0.5590	0.4392	0.164*
H2A	0.5829	0.6161	0.3704	0.164*
H4B	0.5840	0.7361	0.2795	0.164*
H3B	−0.0165	0.3822	0.2921	0.164*
H4A	0.6268	0.6659	0.2578	0.164*
H3A	−0.1042	0.3943	0.2288	0.164*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.0598 (3)	0.0443 (3)	0.0499 (2)	−0.00426 (18)	0.02434 (19)	0.00121 (18)
Cl1	0.0813 (6)	0.0795 (6)	0.0672 (5)	−0.0049 (4)	0.0219 (4)	0.0133 (5)
O1	0.0622 (11)	0.0429 (11)	0.0748 (12)	−0.0012 (9)	0.0311 (10)	0.0095 (9)
N1	0.0587 (13)	0.0578 (15)	0.0563 (14)	−0.0071 (11)	0.0234 (11)	−0.0016 (11)
N4	0.0682 (15)	0.0610 (16)	0.0517 (13)	−0.0122 (12)	0.0296 (12)	−0.0051 (11)
N2	0.0799 (17)	0.0600 (16)	0.0507 (13)	−0.0028 (13)	0.0269 (12)	0.0026 (11)
N5	0.0649 (14)	0.0453 (14)	0.0516 (13)	−0.0132 (10)	0.0214 (11)	0.0003 (10)
C26	0.0653 (17)	0.0449 (17)	0.0709 (18)	−0.0069 (13)	0.0324 (15)	−0.0019 (13)
C24	0.0546 (16)	0.0631 (19)	0.0493 (16)	−0.0204 (14)	0.0144 (13)	0.0031 (14)
C25	0.0564 (16)	0.0406 (16)	0.0505 (15)	−0.0014 (12)	0.0195 (12)	0.0015 (12)
C12	0.0499 (15)	0.0494 (17)	0.0587 (17)	0.0060 (12)	0.0129 (13)	−0.0059 (13)
O2	0.0738 (13)	0.0516 (12)	0.1163 (17)	0.0112 (10)	0.0529 (13)	0.0238 (11)
O1W	0.0847 (15)	0.0566 (13)	0.135 (2)	0.0093 (11)	0.0699 (15)	0.0130 (12)
C11	0.0605 (16)	0.0525 (18)	0.0488 (15)	0.0108 (14)	0.0142 (13)	−0.0016 (13)
C23	0.0498 (15)	0.0540 (18)	0.0667 (18)	−0.0092 (13)	0.0199 (14)	0.0102 (14)
N3	0.0652 (14)	0.0460 (13)	0.0598 (14)	−0.0022 (11)	0.0323 (12)	0.0017 (11)
C28	0.0587 (16)	0.0483 (16)	0.0517 (15)	−0.0104 (13)	0.0282 (13)	−0.0044 (12)
C4	0.0581 (18)	0.065 (2)	0.078 (2)	−0.0024 (15)	0.0133 (16)	−0.0079 (17)
C7	0.080 (2)	0.072 (2)	0.0505 (18)	0.0165 (18)	0.0094 (16)	−0.0062 (16)
O3	0.1086 (17)	0.0688 (15)	0.0521 (12)	−0.0079 (12)	0.0112 (11)	0.0065 (11)
C27	0.0548 (15)	0.0541 (18)	0.0517 (16)	−0.0061 (13)	0.0211 (13)	0.0021 (13)
C9	0.144 (4)	0.099 (3)	0.060 (2)	0.006 (3)	0.051 (2)	0.012 (2)
C33	0.085 (2)	0.067 (2)	0.0584 (18)	−0.0214 (17)	0.0242 (16)	−0.0063 (15)
C16	0.080 (2)	0.105 (3)	0.0505 (19)	−0.030 (2)	0.0132 (17)	0.0073 (19)
C8	0.131 (3)	0.092 (3)	0.0491 (19)	0.019 (3)	0.024 (2)	−0.0004 (19)
C14	0.130 (4)	0.124 (4)	0.074 (3)	−0.037 (3)	0.062 (3)	−0.029 (2)
C29	0.0675 (19)	0.058 (2)	0.073 (2)	−0.0047 (15)	0.0239 (16)	0.0007 (15)
C5	0.083 (2)	0.099 (3)	0.082 (3)	−0.018 (2)	0.005 (2)	−0.027 (2)
C13	0.096 (2)	0.084 (2)	0.071 (2)	−0.0146 (19)	0.0489 (19)	−0.0174 (18)
C22	0.102 (3)	0.059 (2)	0.092 (2)	0.0085 (18)	0.058 (2)	0.0039 (17)
C19	0.0592 (19)	0.069 (2)	0.101 (3)	0.0014 (16)	0.0186 (19)	0.023 (2)
C1	0.077 (2)	0.075 (2)	0.071 (2)	−0.0194 (17)	0.0347 (17)	−0.0065 (16)
C10	0.120 (3)	0.085 (3)	0.062 (2)	−0.014 (2)	0.047 (2)	0.0040 (17)
O4W	0.1006 (17)	0.111 (2)	0.0916 (16)	0.0294 (15)	0.0437 (14)	0.0281 (15)
O3W	0.126 (2)	0.0917 (18)	0.0632 (14)	0.0122 (15)	0.0093 (14)	−0.0117 (12)
O2W	0.0884 (16)	0.1063 (19)	0.145 (2)	0.0433 (14)	0.0775 (16)	0.0619 (17)
C30	0.108 (3)	0.060 (2)	0.095 (3)	0.011 (2)	0.028 (2)	0.011 (2)
C2	0.079 (2)	0.085 (3)	0.098 (3)	−0.0245 (19)	0.044 (2)	−0.003 (2)
C18	0.079 (3)	0.127 (4)	0.115 (4)	0.010 (3)	−0.002 (3)	0.058 (3)
C3	0.067 (2)	0.082 (3)	0.113 (3)	−0.0231 (18)	0.030 (2)	−0.015 (2)
C32	0.144 (4)	0.067 (3)	0.078 (2)	−0.053 (2)	0.033 (2)	−0.017 (2)
C15	0.123 (4)	0.141 (4)	0.052 (2)	−0.052 (3)	0.030 (2)	−0.009 (2)
C21	0.127 (3)	0.076 (3)	0.158 (4)	0.025 (3)	0.093 (3)	0.008 (3)
C20	0.082 (3)	0.078 (3)	0.161 (4)	0.024 (2)	0.053 (3)	0.029 (3)
C17	0.100 (3)	0.141 (4)	0.068 (3)	−0.014 (3)	−0.003 (2)	0.037 (3)
C6	0.104 (3)	0.104 (3)	0.061 (2)	−0.002 (2)	0.002 (2)	−0.026 (2)
C31	0.173 (4)	0.056 (2)	0.090 (3)	−0.015 (3)	0.046 (3)	0.000 (2)
O5A	0.228 (6)	0.090 (3)	0.156 (5)	−0.004 (4)	0.062 (4)	−0.048 (3)
O4A	0.079 (3)	0.166 (5)	0.112 (3)	−0.026 (3)	0.003 (2)	−0.019 (3)
O6A	0.128 (4)	0.193 (6)	0.135 (4)	−0.013 (4)	0.088 (3)	0.026 (4)
O7A	0.190 (5)	0.112 (4)	0.097 (3)	0.013 (4)	0.044 (4)	0.048 (3)
O4B	0.176 (11)	0.131 (9)	0.135 (9)	−0.025 (7)	0.048 (7)	0.067 (7)
O5B	0.176 (11)	0.212 (13)	0.215 (12)	0.012 (8)	0.106 (9)	−0.035 (9)
O6B	0.164 (10)	0.146 (10)	0.120 (9)	−0.069 (7)	0.062 (7)	−0.034 (7)
O7B	0.092 (7)	0.133 (9)	0.088 (7)	0.006 (6)	0.014 (5)	0.004 (6)

Geometric parameters (Å, º)

Mn1—O1W	2.123 (2)	C9—C8	1.345 (5)
Mn1—O1	2.1249 (17)	C9—C10	1.394 (5)
Mn1—N3	2.264 (2)	C9—H9	0.9300
Mn1—N2	2.288 (2)	C33—C32	1.383 (5)
Mn1—N4	2.289 (2)	C33—H33	0.9300
Mn1—N1	2.300 (2)	C16—C15	1.403 (6)
Cl1—O4B	1.331 (9)	C16—C17	1.419 (6)
Cl1—O7A	1.365 (4)	C8—H8	0.9300
Cl1—O5B	1.374 (8)	C14—C15	1.341 (6)
Cl1—O4A	1.400 (3)	C14—C13	1.402 (5)
Cl1—O6B	1.415 (8)	C14—H14	0.9300
Cl1—O5A	1.422 (4)	C29—C30	1.378 (4)
Cl1—O6A	1.426 (4)	C29—H29	0.9300
Cl1—O7B	1.436 (7)	C5—C6	1.335 (5)
O1—C25	1.261 (3)	C5—H5	0.9300
N1—C1	1.332 (3)	C13—H13	0.9300
N1—C12	1.365 (3)	C22—C21	1.387 (5)
N4—C13	1.326 (4)	C22—H22	0.9300
N4—C24	1.355 (4)	C19—C20	1.401 (5)
N2—C10	1.327 (4)	C19—C18	1.438 (5)
N2—C11	1.355 (4)	C1—C2	1.392 (4)
N5—C27	1.334 (3)	C1—H1	0.9300
N5—C26	1.433 (3)	C10—H10	0.9300
N5—H5A	0.8600	O4W—H4B	0.8797
C26—C25	1.507 (3)	O4W—H4A	0.9192
C26—H26B	0.9700	O3W—H3B	0.8986
C26—H26A	0.9700	O3W—H3A	0.9027
C24—C16	1.410 (4)	O2W—H2B	0.8993
C24—C23	1.439 (4)	O2W—H2A	0.8948
C25—O2	1.238 (3)	C30—C31	1.352 (5)
C12—C4	1.407 (4)	C30—H30	0.9300
C12—C11	1.431 (4)	C2—C3	1.357 (5)
O1W—H1B	0.8908	C2—H2	0.9300
O1W—H1A	0.8992	C18—C17	1.329 (6)
C11—C7	1.407 (4)	C18—H18	0.9300
C23—N3	1.355 (3)	C3—H3	0.9300
C23—C19	1.401 (4)	C32—C31	1.366 (5)
N3—C22	1.328 (3)	C32—H32	0.9300
C28—C29	1.374 (4)	C15—H15	0.9300
C28—C33	1.380 (4)	C21—C20	1.349 (6)
C28—C27	1.492 (4)	C21—H21	0.9300
C4—C3	1.399 (5)	C20—H20	0.9300
C4—C5	1.423 (5)	C17—H17	0.9300
C7—C8	1.393 (5)	C6—H6	0.9300
C7—C6	1.427 (5)	C31—H31	0.9300
O3—C27	1.225 (3)
O1W—Mn1—O1	88.04 (7)	O3—C27—N5	121.5 (3)
O1W—Mn1—N3	162.17 (9)	O3—C27—C28	122.1 (3)
O1—Mn1—N3	88.40 (7)	N5—C27—C28	116.4 (2)
O1W—Mn1—N2	99.55 (9)	C8—C9—C10	119.1 (3)
O1—Mn1—N2	90.30 (8)	C8—C9—H9	120.4
N3—Mn1—N2	97.93 (8)	C10—C9—H9	120.4
O1W—Mn1—N4	91.24 (9)	C28—C33—C32	119.9 (3)
O1—Mn1—N4	104.75 (7)	C28—C33—H33	120.1
N3—Mn1—N4	72.82 (8)	C32—C33—H33	120.1
N2—Mn1—N4	161.82 (9)	C15—C16—C24	116.4 (4)
O1W—Mn1—N1	96.74 (8)	C15—C16—C17	124.3 (4)
O1—Mn1—N1	162.53 (8)	C24—C16—C17	119.2 (4)
N3—Mn1—N1	91.85 (8)	C9—C8—C7	120.3 (3)
N2—Mn1—N1	72.36 (8)	C9—C8—H8	119.9
N4—Mn1—N1	91.98 (8)	C7—C8—H8	119.9
O4B—Cl1—O5B	119.3 (8)	C15—C14—C13	119.2 (4)
O7A—Cl1—O4A	112.8 (3)	C15—C14—H14	120.4
O4B—Cl1—O6B	115.1 (8)	C13—C14—H14	120.4
O5B—Cl1—O6B	108.2 (8)	C28—C29—C30	120.6 (3)
O7A—Cl1—O5A	109.6 (3)	C28—C29—H29	119.7
O4A—Cl1—O5A	109.7 (3)	C30—C29—H29	119.7
O7A—Cl1—O6A	110.4 (3)	C6—C5—C4	121.7 (4)
O4A—Cl1—O6A	106.9 (3)	C6—C5—H5	119.2
O5A—Cl1—O6A	107.2 (4)	C4—C5—H5	119.2
O4B—Cl1—O7B	107.0 (7)	N4—C13—C14	122.5 (4)
O5B—Cl1—O7B	103.8 (8)	N4—C13—H13	118.7
O6B—Cl1—O7B	101.1 (7)	C14—C13—H13	118.7
C25—O1—Mn1	131.12 (17)	N3—C22—C21	122.9 (3)
C1—N1—C12	117.7 (2)	N3—C22—H22	118.5
C1—N1—Mn1	126.96 (19)	C21—C22—H22	118.5
C12—N1—Mn1	115.22 (17)	C23—C19—C20	117.6 (3)
C13—N4—C24	118.1 (3)	C23—C19—C18	118.4 (4)
C13—N4—Mn1	126.6 (2)	C20—C19—C18	124.0 (4)
C24—N4—Mn1	115.27 (17)	N1—C1—C2	123.6 (3)
C10—N2—C11	117.6 (3)	N1—C1—H1	118.2
C10—N2—Mn1	126.2 (2)	C2—C1—H1	118.2
C11—N2—Mn1	116.12 (17)	N2—C10—C9	123.1 (4)
C27—N5—C26	121.7 (2)	N2—C10—H10	118.4
C27—N5—H5A	119.2	C9—C10—H10	118.4
C26—N5—H5A	119.2	H4B—O4W—H4A	100.9
N5—C26—C25	115.5 (2)	H3B—O3W—H3A	93.8
N5—C26—H26B	108.4	H2B—O2W—H2A	106.0
C25—C26—H26B	108.4	C31—C30—C29	120.1 (3)
N5—C26—H26A	108.4	C31—C30—H30	120.0
C25—C26—H26A	108.4	C29—C30—H30	120.0
H26B—C26—H26A	107.5	C3—C2—C1	118.2 (3)
N4—C24—C16	122.8 (3)	C3—C2—H2	120.9
N4—C24—C23	118.0 (2)	C1—C2—H2	120.9
C16—C24—C23	119.2 (3)	C17—C18—C19	121.6 (4)
O2—C25—O1	125.1 (2)	C17—C18—H18	119.2
O2—C25—C26	120.1 (2)	C19—C18—H18	119.2
O1—C25—C26	114.8 (2)	C2—C3—C4	121.1 (3)
N1—C12—C4	122.3 (3)	C2—C3—H3	119.5
N1—C12—C11	118.1 (2)	C4—C3—H3	119.5
C4—C12—C11	119.6 (3)	C31—C32—C33	120.1 (3)
Mn1—O1W—H1B	110.3	C31—C32—H32	119.9
Mn1—O1W—H1A	142.1	C33—C32—H32	119.9
H1B—O1W—H1A	107.6	C14—C15—C16	120.8 (4)
N2—C11—C7	122.5 (3)	C14—C15—H15	119.6
N2—C11—C12	117.9 (2)	C16—C15—H15	119.6
C7—C11—C12	119.6 (3)	C20—C21—C22	119.7 (4)
N3—C23—C19	122.4 (3)	C20—C21—H21	120.1
N3—C23—C24	117.6 (2)	C22—C21—H21	120.1
C19—C23—C24	120.0 (3)	C21—C20—C19	119.5 (4)
C22—N3—C23	117.8 (3)	C21—C20—H20	120.3
C22—N3—Mn1	125.9 (2)	C19—C20—H20	120.3
C23—N3—Mn1	116.34 (18)	C18—C17—C16	121.5 (4)
C29—C28—C33	119.0 (3)	C18—C17—H17	119.2
C29—C28—C27	121.6 (2)	C16—C17—H17	119.2
C33—C28—C27	119.4 (3)	C5—C6—C7	121.2 (3)
C3—C4—C12	117.0 (3)	C5—C6—H6	119.4
C3—C4—C5	124.1 (3)	C7—C6—H6	119.4
C12—C4—C5	118.9 (3)	C30—C31—C32	120.4 (4)
C8—C7—C11	117.3 (3)	C30—C31—H31	119.8
C8—C7—C6	123.8 (3)	C32—C31—H31	119.8
C11—C7—C6	118.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1B···O2	0.90	1.83	2.645 (3)	152
O2W—H2B···O2^i	0.90	1.84	2.701 (3)	160
O3W—H3B···O3	0.90	1.85	2.745 (3)	178
O1W—H1A···O2W	0.90	1.71	2.595 (4)	166
O2W—H2A···O4W	0.90	1.90	2.760 (4)	158
O4W—H4B···O3W^ii	0.88	1.98	2.816 (4)	157
C3—H3···Cg1^iii	0.93	2.75	3.680 (4)	174
C5—H5···Cg2^iii	0.93	3.04	3.961 (5)	172

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