Aqua­bis(2,2'-bi­pyridine)(3-carboxyl­ato-4-hydroxy­benzene­sulfonato)­manganese(II) dihydrate

The Mn atom in the title compound, [Mn(C₇H₄O₆S)(C₁₀H₈N₂)₂(H₂O)]·2H₂O, is coordinated by the two N-heterocycles, a water mol­ecule and a 3-carboxyl­ato-4-hydroxy­benzene­sulfonate dianion through the carboxyl­ate group, thus imposing an octahedral environment on the metal atom. The coordinated and uncoordinated water mol­ecules, the carboxyl­ate and sulfonate groups interact via hydrogen bonds, producing a three-dimensional network architecture.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.125
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6

   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
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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.

Aquabis(2,2'-bipyridine)(3-carboxylato-4-hydroxybenzenesulfonato)manganese(II) dihydrate

Crystal data

[Mn(C7H4O6S)(C10H8N2)2(H2O)]·2H2O	Z = 2
Mr = 637.52	F(000) = 658
Triclinic, P1	Dx = 1.469 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8406 (6) Å	Cell parameters from 3913 reflections
b = 10.1729 (6) Å	θ = 2.5–25.9°
c = 15.2354 (9) Å	µ = 0.59 mm^−1
α = 73.5009 (13)°	T = 298 K
β = 84.7304 (14)°	Block, pale yellow
γ = 80.7830 (13)°	0.33 × 0.22 × 0.14 mm
V = 1441.76 (15) Å^3

Data collection

Bruker APEX area-detector diffractometer	6350 independent reflections
Radiation source: fine-focus sealed tube	5289 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→12
Tmin = 0.829, Tmax = 0.922	k = −13→13
12401 measured reflections	l = −19→19

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0667P)^2 + 0.2944P] where P = (Fo^2 + 2Fc^2)/3
6350 reflections	(Δ/σ)max = 0.001
435 parameters	Δρmax = 0.37 e Å^−3
22 restraints	Δρmin = −0.25 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Mn1	0.66514 (3)	0.37459 (3)	0.72077 (2)	0.03845 (12)
S1	0.15269 (8)	0.89654 (6)	0.70579 (5)	0.05640 (19)
N1	0.8862 (2)	0.3996 (2)	0.67331 (14)	0.0452 (5)
N2	0.6648 (2)	0.5723 (2)	0.60489 (13)	0.0434 (4)
N3	0.6575 (2)	0.5032 (2)	0.82460 (14)	0.0471 (5)
N4	0.7248 (2)	0.2279 (2)	0.85734 (13)	0.0478 (5)
O1	0.44885 (17)	0.40819 (18)	0.73177 (13)	0.0527 (4)
O2	0.3487 (2)	0.25030 (18)	0.83930 (13)	0.0633 (5)
O3	0.1105 (2)	0.3160 (2)	0.90628 (15)	0.0719 (6)
H3o	0.186 (2)	0.270 (3)	0.892 (2)	0.084 (12)*
O4	0.0882 (4)	0.9232 (3)	0.6222 (2)	0.0720 (11)	0.744 (8)
O5	0.0903 (6)	0.9790 (3)	0.7650 (2)	0.0935 (19)	0.744 (8)
O6	0.3019 (3)	0.9051 (3)	0.6895 (3)	0.0826 (15)	0.744 (8)
O4'	0.1969 (18)	0.8908 (10)	0.6132 (5)	0.093 (5)	0.256 (8)
O5'	0.0076 (7)	0.9608 (10)	0.6994 (11)	0.114 (7)	0.256 (8)
O6'	0.2380 (17)	0.9483 (12)	0.7500 (8)	0.106 (7)	0.256 (8)
O1w	0.6617 (2)	0.2168 (2)	0.65556 (15)	0.0643 (5)
H1w1	0.722 (3)	0.183 (3)	0.621 (2)	0.089 (12)*
H1w2	0.603 (3)	0.162 (3)	0.676 (2)	0.077 (11)*
O2w	0.8646 (3)	0.1236 (3)	0.55065 (18)	0.0786 (6)
H2w1	0.863 (4)	0.111 (5)	0.4981 (15)	0.117 (16)*
H2w2	0.906 (4)	0.050 (2)	0.585 (2)	0.102 (14)*
O3w	0.4783 (3)	0.0517 (2)	0.7500 (2)	0.0797 (7)
H3w1	0.421 (3)	0.013 (4)	0.732 (3)	0.102 (14)*
H3w2	0.434 (4)	0.105 (3)	0.779 (3)	0.105 (14)*
C1	0.3550 (3)	0.3727 (2)	0.79118 (16)	0.0441 (5)
C2	0.2405 (2)	0.4824 (2)	0.80386 (15)	0.0380 (5)
C3	0.1232 (3)	0.4484 (3)	0.86009 (17)	0.0473 (6)
C4	0.0179 (3)	0.5516 (3)	0.8691 (2)	0.0604 (7)
H4	−0.0593	0.5291	0.9072	0.072*
C5	0.0260 (3)	0.6869 (3)	0.8223 (2)	0.0570 (7)
H5	−0.0466	0.7554	0.8278	0.068*
C6	0.1415 (2)	0.7224 (2)	0.76685 (16)	0.0414 (5)
C7	0.2473 (2)	0.6202 (2)	0.75835 (15)	0.0379 (5)
H7	0.3251	0.6439	0.7213	0.046*
C8	0.9940 (3)	0.2999 (3)	0.69448 (19)	0.0543 (6)
H8	0.9781	0.2131	0.7313	0.065*
C9	1.1268 (3)	0.3198 (3)	0.6643 (2)	0.0601 (7)
H9	1.1990	0.2475	0.6789	0.072*
C10	1.1507 (3)	0.4485 (3)	0.6123 (2)	0.0620 (7)
H10	1.2401	0.4654	0.5923	0.074*
C11	1.0408 (3)	0.5533 (3)	0.58965 (19)	0.0554 (6)
H11	1.0554	0.6415	0.5546	0.067*
C12	0.9093 (2)	0.5250 (2)	0.61983 (16)	0.0431 (5)
C13	0.7843 (3)	0.6253 (2)	0.58981 (16)	0.0452 (5)
C14	0.7885 (3)	0.7626 (3)	0.5432 (2)	0.0700 (9)
H14	0.8711	0.7991	0.5347	0.084*
C15	0.6695 (4)	0.8450 (3)	0.5094 (2)	0.0822 (10)
H15	0.6712	0.9376	0.4779	0.099*
C16	0.5489 (3)	0.7903 (3)	0.5221 (2)	0.0712 (9)
H16	0.4679	0.8439	0.4984	0.085*
C17	0.5504 (3)	0.6541 (3)	0.57102 (18)	0.0554 (6)
H17	0.4681	0.6170	0.5810	0.067*
C18	0.6192 (3)	0.6399 (3)	0.8062 (2)	0.0584 (7)
H18	0.6000	0.6894	0.7462	0.070*
C19	0.6066 (3)	0.7110 (3)	0.8718 (2)	0.0626 (7)
H19	0.5802	0.8063	0.8564	0.075*
C20	0.6339 (3)	0.6379 (3)	0.9602 (2)	0.0622 (7)
H20	0.6267	0.6833	1.0059	0.075*
C21	0.6722 (3)	0.4972 (3)	0.98081 (18)	0.0544 (6)
H21	0.6898	0.4462	1.0408	0.065*
C22	0.6842 (2)	0.4317 (3)	0.91168 (16)	0.0424 (5)
C23	0.7262 (2)	0.2796 (3)	0.92914 (16)	0.0450 (5)
C24	0.7660 (3)	0.1944 (3)	1.01380 (19)	0.0677 (8)
H24	0.7653	0.2311	1.0633	0.081*
C25	0.8065 (4)	0.0555 (3)	1.0243 (2)	0.0800 (10)
H25	0.8345	−0.0023	1.0807	0.096*
C26	0.8054 (4)	0.0028 (3)	0.9516 (2)	0.0779 (9)
H26	0.8321	−0.0911	0.9576	0.093*
C27	0.7640 (3)	0.0916 (3)	0.8691 (2)	0.0648 (8)
H27	0.7631	0.0558	0.8194	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.0448 (2)	0.03194 (19)	0.0361 (2)	−0.00390 (14)	−0.00063 (14)	−0.00659 (14)
S1	0.0792 (5)	0.0337 (3)	0.0514 (4)	−0.0005 (3)	−0.0044 (3)	−0.0075 (3)
N1	0.0487 (11)	0.0381 (10)	0.0490 (11)	−0.0041 (8)	−0.0016 (9)	−0.0137 (9)
N2	0.0465 (11)	0.0400 (10)	0.0382 (10)	−0.0024 (8)	0.0002 (8)	−0.0048 (8)
N3	0.0556 (12)	0.0405 (11)	0.0455 (11)	−0.0045 (9)	−0.0025 (9)	−0.0138 (9)
N4	0.0593 (13)	0.0393 (11)	0.0410 (11)	−0.0058 (9)	−0.0032 (9)	−0.0052 (9)
O1	0.0429 (9)	0.0514 (10)	0.0598 (11)	0.0009 (8)	0.0043 (8)	−0.0151 (8)
O2	0.0806 (14)	0.0370 (9)	0.0619 (12)	0.0010 (9)	0.0007 (10)	−0.0033 (8)
O3	0.0803 (15)	0.0508 (12)	0.0751 (14)	−0.0275 (11)	0.0199 (12)	0.0003 (10)
O4	0.092 (3)	0.0637 (19)	0.0498 (17)	0.0094 (18)	−0.0133 (18)	−0.0070 (14)
O5	0.171 (5)	0.0441 (16)	0.0605 (19)	0.014 (2)	−0.006 (2)	−0.0216 (14)
O6	0.087 (2)	0.0464 (17)	0.109 (3)	−0.0265 (15)	−0.017 (2)	−0.0007 (18)
O4'	0.165 (15)	0.053 (6)	0.051 (5)	−0.026 (7)	0.019 (7)	0.001 (4)
O5'	0.073 (7)	0.050 (5)	0.184 (18)	0.010 (5)	0.003 (7)	0.011 (7)
O6'	0.181 (17)	0.075 (7)	0.078 (8)	−0.081 (10)	−0.040 (10)	−0.004 (6)
O1w	0.0639 (13)	0.0634 (13)	0.0792 (14)	−0.0194 (10)	0.0170 (11)	−0.0420 (11)
O2w	0.0798 (15)	0.0857 (17)	0.0672 (15)	0.0130 (13)	0.0010 (12)	−0.0308 (14)
O3w	0.0696 (15)	0.0610 (14)	0.117 (2)	−0.0175 (12)	0.0096 (14)	−0.0374 (14)
C1	0.0515 (14)	0.0371 (12)	0.0435 (13)	−0.0031 (10)	−0.0066 (11)	−0.0114 (10)
C2	0.0404 (12)	0.0368 (11)	0.0363 (11)	−0.0080 (9)	−0.0004 (9)	−0.0082 (9)
C3	0.0517 (14)	0.0450 (13)	0.0447 (13)	−0.0170 (11)	0.0050 (10)	−0.0082 (10)
C4	0.0451 (14)	0.0680 (18)	0.0694 (18)	−0.0188 (13)	0.0179 (13)	−0.0216 (15)
C5	0.0466 (14)	0.0560 (16)	0.0688 (18)	0.0010 (12)	0.0035 (12)	−0.0240 (14)
C6	0.0467 (13)	0.0384 (12)	0.0406 (12)	−0.0058 (10)	−0.0007 (10)	−0.0137 (10)
C7	0.0413 (12)	0.0382 (11)	0.0347 (11)	−0.0100 (9)	0.0030 (9)	−0.0096 (9)
C8	0.0564 (16)	0.0437 (14)	0.0629 (16)	0.0017 (11)	−0.0094 (13)	−0.0176 (12)
C9	0.0480 (15)	0.0706 (19)	0.0668 (18)	0.0069 (13)	−0.0127 (13)	−0.0323 (15)
C10	0.0428 (14)	0.088 (2)	0.0649 (18)	−0.0131 (14)	−0.0032 (12)	−0.0347 (16)
C11	0.0550 (15)	0.0620 (17)	0.0543 (15)	−0.0211 (13)	0.0019 (12)	−0.0184 (13)
C12	0.0479 (13)	0.0429 (13)	0.0421 (12)	−0.0078 (10)	0.0012 (10)	−0.0174 (10)
C13	0.0547 (14)	0.0383 (12)	0.0407 (12)	−0.0066 (10)	0.0068 (10)	−0.0105 (10)
C14	0.0701 (19)	0.0432 (15)	0.087 (2)	−0.0121 (14)	0.0215 (16)	−0.0071 (14)
C15	0.091 (2)	0.0408 (15)	0.091 (2)	0.0000 (16)	0.0201 (19)	0.0071 (15)
C16	0.076 (2)	0.0543 (17)	0.0607 (18)	0.0158 (15)	−0.0018 (15)	0.0063 (14)
C17	0.0555 (15)	0.0543 (15)	0.0487 (14)	−0.0026 (12)	−0.0023 (12)	−0.0045 (12)
C18	0.0724 (18)	0.0470 (15)	0.0557 (16)	−0.0024 (13)	−0.0042 (13)	−0.0169 (12)
C19	0.0644 (18)	0.0514 (16)	0.080 (2)	−0.0058 (13)	0.0008 (15)	−0.0326 (15)
C20	0.0610 (17)	0.076 (2)	0.0648 (18)	−0.0171 (14)	0.0084 (14)	−0.0421 (16)
C21	0.0533 (15)	0.0717 (18)	0.0457 (14)	−0.0191 (13)	0.0055 (11)	−0.0247 (13)
C22	0.0366 (12)	0.0535 (14)	0.0402 (12)	−0.0133 (10)	0.0032 (9)	−0.0154 (10)
C23	0.0412 (12)	0.0527 (14)	0.0391 (12)	−0.0111 (10)	−0.0008 (9)	−0.0073 (11)
C24	0.090 (2)	0.070 (2)	0.0423 (15)	−0.0162 (16)	−0.0128 (14)	−0.0083 (13)
C25	0.109 (3)	0.063 (2)	0.0535 (18)	−0.0039 (18)	−0.0221 (17)	0.0085 (15)
C26	0.109 (3)	0.0470 (16)	0.064 (2)	0.0000 (16)	−0.0145 (18)	0.0052 (14)
C27	0.092 (2)	0.0418 (14)	0.0545 (16)	−0.0050 (14)	−0.0065 (15)	−0.0045 (12)

Geometric parameters (Å, º)

Mn1—O1	2.0998 (17)	C15—C16	1.365 (5)
Mn1—O1w	2.1200 (19)	C16—C17	1.373 (4)
Mn1—N1	2.259 (2)	C18—C19	1.377 (4)
Mn1—N2	2.2681 (19)	C19—C20	1.368 (4)
Mn1—N3	2.311 (2)	C20—C21	1.372 (4)
Mn1—N4	2.254 (2)	C21—C22	1.385 (3)
S1—O6'	1.372 (6)	C22—C23	1.489 (4)
S1—O4	1.412 (3)	C23—C24	1.385 (4)
S1—O5	1.434 (3)	C24—C25	1.373 (5)
S1—O4'	1.452 (6)	C25—C26	1.362 (5)
S1—O5'	1.472 (6)	C26—C27	1.376 (4)
S1—O6	1.479 (3)	O3—H3o	0.86 (3)
S1—C6	1.767 (2)	O1w—H1w1	0.85 (3)
N1—C8	1.338 (3)	O1w—H1w2	0.84 (3)
N1—C12	1.346 (3)	O2w—H2w1	0.85 (3)
N2—C17	1.337 (3)	O2w—H2w2	0.85 (3)
N2—C13	1.345 (3)	O3w—H3w1	0.84 (3)
N3—C18	1.336 (3)	O3w—H3w2	0.84 (4)
N3—C22	1.347 (3)	C4—H4	0.93
N4—C27	1.343 (3)	C5—H5	0.93
N4—C23	1.344 (3)	C7—H7	0.93
O1—C1	1.253 (3)	C8—H8	0.93
O2—C1	1.261 (3)	C9—H9	0.93
O3—C3	1.350 (3)	C10—H10	0.93
C1—C2	1.493 (3)	C11—H11	0.93
C2—C7	1.386 (3)	C14—H14	0.93
C2—C3	1.402 (3)	C15—H15	0.93
C3—C4	1.379 (4)	C16—H16	0.93
C4—C5	1.370 (4)	C17—H17	0.93
C5—C6	1.386 (3)	C18—H18	0.93
C6—C7	1.374 (3)	C19—H19	0.93
C8—C9	1.372 (4)	C20—H20	0.93
C9—C10	1.369 (4)	C21—H21	0.93
C10—C11	1.384 (4)	C24—H24	0.93
C11—C12	1.380 (3)	C25—H25	0.93
C12—C13	1.483 (3)	C26—H26	0.93
C13—C14	1.382 (4)	C27—H27	0.93
C14—C15	1.374 (5)
O1—Mn1—O1w	90.98 (8)	C14—C13—C12	123.2 (2)
O1—Mn1—N1	162.14 (7)	C15—C14—C13	119.4 (3)
O1—Mn1—N2	90.20 (7)	C16—C15—C14	119.8 (3)
O1—Mn1—N3	86.13 (7)	C15—C16—C17	118.2 (3)
O1—Mn1—N4	103.90 (7)	N2—C17—C16	123.0 (3)
O1w—Mn1—N1	93.16 (8)	N3—C18—C19	123.2 (3)
O1w—Mn1—N2	104.96 (8)	C20—C19—C18	118.4 (3)
O1w—Mn1—N3	165.57 (8)	C19—C20—C21	119.4 (3)
O1w—Mn1—N4	95.07 (8)	C20—C21—C22	119.5 (3)
N1—Mn1—N2	71.94 (7)	N3—C22—C21	121.3 (2)
N1—Mn1—N3	93.90 (7)	N3—C22—C23	116.4 (2)
N1—Mn1—N4	93.04 (7)	C21—C22—C23	122.3 (2)
N2—Mn1—N4	155.34 (8)	N4—C23—C24	120.9 (2)
N2—Mn1—N3	89.21 (7)	N4—C23—C22	116.3 (2)
N3—Mn1—N4	72.00 (7)	C24—C23—C22	122.8 (2)
O4—S1—O5	115.0 (2)	C25—C24—C23	119.6 (3)
O4—S1—O6	110.9 (2)	C26—C25—C24	119.6 (3)
O5—S1—O6	111.2 (3)	C25—C26—C27	118.5 (3)
O4'—S1—O5'	104.7 (9)	N4—C27—C26	122.7 (3)
O4'—S1—O6'	116.6 (8)	C3—O3—H3o	104 (2)
O5'—S1—O6'	117.7 (9)	Mn1—O1w—H1w1	131 (2)
O6'—S1—C6	108.8 (4)	Mn1—O1w—H1w2	117 (2)
O4—S1—C6	107.48 (16)	H1w1—O1w—H1w2	110 (3)
O5—S1—C6	106.35 (16)	H2w1—O2w—H2w2	108 (4)
O4'—S1—C6	104.3 (4)	H3w1—O3w—H3w2	107 (4)
O5'—S1—C6	103.3 (4)	C5—C4—H4	119.7
O6—S1—C6	105.28 (14)	C3—C4—H4	119.7
C8—N1—C12	118.4 (2)	C4—C5—H5	119.8
C8—N1—Mn1	124.93 (17)	C6—C5—H5	119.8
C12—N1—Mn1	116.66 (15)	C6—C7—H7	119.3
C17—N2—C13	118.7 (2)	C2—C7—H7	119.3
C17—N2—Mn1	124.02 (17)	N1—C8—H8	118.5
C13—N2—Mn1	114.62 (15)	C9—C8—H8	118.5
C18—N3—C22	118.2 (2)	C10—C9—H9	120.7
C18—N3—Mn1	125.11 (17)	C8—C9—H9	120.7
C22—N3—Mn1	116.47 (15)	C9—C10—H10	120.3
C27—N4—C23	118.6 (2)	C11—C10—H10	120.3
C27—N4—Mn1	122.66 (18)	C12—C11—H11	120.5
C23—N4—Mn1	118.69 (16)	C10—C11—H11	120.5
C1—O1—Mn1	137.71 (16)	C15—C14—H14	120.3
O1—C1—O2	124.5 (2)	C13—C14—H14	120.3
O1—C1—C2	117.7 (2)	C16—C15—H15	120.1
O2—C1—C2	117.8 (2)	C14—C15—H15	120.1
C7—C2—C3	118.7 (2)	C15—C16—H16	120.9
C7—C2—C1	120.3 (2)	C17—C16—H16	120.9
C3—C2—C1	121.1 (2)	N2—C17—H17	118.5
O3—C3—C4	118.8 (2)	C16—C17—H17	118.5
O3—C3—C2	121.4 (2)	N3—C18—H18	118.4
C4—C3—C2	119.8 (2)	C19—C18—H18	118.4
C5—C4—C3	120.6 (2)	C20—C19—H19	120.8
C4—C5—C6	120.4 (2)	C18—C19—H19	120.8
C7—C6—C5	119.3 (2)	C19—C20—H20	120.3
C7—C6—S1	119.94 (18)	C21—C20—H20	120.3
C5—C6—S1	120.78 (19)	C20—C21—H21	120.2
C6—C7—C2	121.3 (2)	C22—C21—H21	120.2
N1—C8—C9	123.0 (3)	C25—C24—H24	120.2
C10—C9—C8	118.6 (3)	C23—C24—H24	120.2
C9—C10—C11	119.4 (3)	C26—C25—H25	120.2
C12—C11—C10	119.0 (3)	C24—C25—H25	120.2
N1—C12—C11	121.5 (2)	C25—C26—H26	120.7
N1—C12—C13	115.5 (2)	C27—C26—H26	120.7
C11—C12—C13	122.7 (2)	N4—C27—H27	118.6
N2—C13—C14	120.9 (2)	C26—C27—H27	118.6
N2—C13—C12	115.8 (2)
O1—Mn1—N1—C8	−163.8 (2)	O5'—S1—C6—C7	156.4 (7)
O1w—Mn1—N1—C8	−60.7 (2)	O6—S1—C6—C7	−25.2 (3)
N4—Mn1—N1—C8	34.5 (2)	O6'—S1—C6—C5	103.3 (9)
N2—Mn1—N1—C8	−165.4 (2)	O4—S1—C6—C5	−85.9 (3)
N3—Mn1—N1—C8	106.7 (2)	O5—S1—C6—C5	37.8 (3)
O1—Mn1—N1—C12	16.2 (3)	O4'—S1—C6—C5	−131.7 (7)
O1w—Mn1—N1—C12	119.35 (17)	O5'—S1—C6—C5	−22.5 (8)
N4—Mn1—N1—C12	−145.40 (17)	O6—S1—C6—C5	155.9 (3)
N2—Mn1—N1—C12	14.64 (16)	C5—C6—C7—C2	0.2 (3)
N3—Mn1—N1—C12	−73.25 (17)	S1—C6—C7—C2	−178.69 (17)
O1—Mn1—N2—C17	−1.4 (2)	C3—C2—C7—C6	−0.6 (3)
O1w—Mn1—N2—C17	89.6 (2)	C1—C2—C7—C6	178.1 (2)
N4—Mn1—N2—C17	−127.1 (2)	C12—N1—C8—C9	0.1 (4)
N1—Mn1—N2—C17	178.1 (2)	Mn1—N1—C8—C9	−179.79 (19)
N3—Mn1—N2—C17	−87.5 (2)	N1—C8—C9—C10	1.8 (4)
O1—Mn1—N2—C13	159.60 (16)	C8—C9—C10—C11	−1.7 (4)
O1w—Mn1—N2—C13	−109.34 (17)	C9—C10—C11—C12	−0.3 (4)
N4—Mn1—N2—C13	33.9 (3)	C8—N1—C12—C11	−2.3 (3)
N1—Mn1—N2—C13	−20.89 (16)	Mn1—N1—C12—C11	177.66 (18)
N3—Mn1—N2—C13	73.47 (16)	C8—N1—C12—C13	172.8 (2)
O1—Mn1—N3—C18	−71.8 (2)	Mn1—N1—C12—C13	−7.2 (3)
O1w—Mn1—N3—C18	−150.6 (3)	C10—C11—C12—N1	2.4 (4)
N4—Mn1—N3—C18	−177.8 (2)	C10—C11—C12—C13	−172.4 (2)
N1—Mn1—N3—C18	90.3 (2)	C17—N2—C13—C14	2.3 (4)
N2—Mn1—N3—C18	18.5 (2)	Mn1—N2—C13—C14	−159.8 (2)
O1—Mn1—N3—C22	103.05 (17)	C17—N2—C13—C12	−173.2 (2)
O1w—Mn1—N3—C22	24.3 (4)	Mn1—N2—C13—C12	24.7 (2)
N4—Mn1—N3—C22	−2.92 (16)	N1—C12—C13—N2	−11.8 (3)
N1—Mn1—N3—C22	−94.86 (17)	C11—C12—C13—N2	163.2 (2)
N2—Mn1—N3—C22	−166.70 (17)	N1—C12—C13—C14	172.8 (3)
O1—Mn1—N4—C27	102.1 (2)	C11—C12—C13—C14	−12.1 (4)
O1w—Mn1—N4—C27	9.8 (2)	N2—C13—C14—C15	−2.0 (5)
N1—Mn1—N4—C27	−83.6 (2)	C12—C13—C14—C15	173.2 (3)
N2—Mn1—N4—C27	−134.7 (2)	C13—C14—C15—C16	0.0 (5)
N3—Mn1—N4—C27	−176.7 (2)	C14—C15—C16—C17	1.7 (5)
O1—Mn1—N4—C23	−80.45 (18)	C13—N2—C17—C16	−0.6 (4)
O1w—Mn1—N4—C23	−172.72 (18)	Mn1—N2—C17—C16	159.7 (2)
N1—Mn1—N4—C23	93.83 (18)	C15—C16—C17—N2	−1.4 (5)
N2—Mn1—N4—C23	42.8 (3)	C22—N3—C18—C19	0.4 (4)
N3—Mn1—N4—C23	0.72 (17)	Mn1—N3—C18—C19	175.2 (2)
O1w—Mn1—O1—C1	97.9 (2)	N3—C18—C19—C20	−0.4 (4)
N4—Mn1—O1—C1	2.4 (2)	C18—C19—C20—C21	−0.3 (4)
N1—Mn1—O1—C1	−158.7 (2)	C19—C20—C21—C22	0.9 (4)
N2—Mn1—O1—C1	−157.2 (2)	C18—N3—C22—C21	0.2 (4)
N3—Mn1—O1—C1	−68.0 (2)	Mn1—N3—C22—C21	−175.01 (17)
Mn1—O1—C1—O2	−47.5 (4)	C18—N3—C22—C23	179.8 (2)
Mn1—O1—C1—C2	134.4 (2)	Mn1—N3—C22—C23	4.6 (3)
O1—C1—C2—C7	−7.0 (3)	C20—C21—C22—N3	−0.8 (4)
O2—C1—C2—C7	174.8 (2)	C20—C21—C22—C23	179.6 (2)
O1—C1—C2—C3	171.6 (2)	C27—N4—C23—C24	−0.5 (4)
O2—C1—C2—C3	−6.6 (3)	Mn1—N4—C23—C24	−178.1 (2)
C7—C2—C3—O3	−179.9 (2)	C27—N4—C23—C22	178.9 (2)
C1—C2—C3—O3	1.4 (4)	Mn1—N4—C23—C22	1.3 (3)
C7—C2—C3—C4	−0.1 (4)	N3—C22—C23—N4	−4.0 (3)
C1—C2—C3—C4	−178.7 (2)	C21—C22—C23—N4	175.6 (2)
O3—C3—C4—C5	−179.1 (3)	N3—C22—C23—C24	175.4 (2)
C2—C3—C4—C5	1.1 (4)	C21—C22—C23—C24	−5.0 (4)
C3—C4—C5—C6	−1.4 (4)	N4—C23—C24—C25	0.9 (5)
C4—C5—C6—C7	0.8 (4)	C22—C23—C24—C25	−178.5 (3)
C4—C5—C6—S1	179.7 (2)	C23—C24—C25—C26	−0.8 (5)
O6'—S1—C6—C7	−77.8 (9)	C24—C25—C26—C27	0.3 (6)
O4—S1—C6—C7	93.0 (3)	C23—N4—C27—C26	0.0 (5)
O5—S1—C6—C7	−143.3 (3)	Mn1—N4—C27—C26	177.5 (3)
O4'—S1—C6—C7	47.2 (7)	C25—C26—C27—N4	0.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2	0.86 (3)	1.73 (2)	2.535 (3)	155 (4)
O1w—H1w1···O2w	0.85 (3)	1.82 (3)	2.667 (3)	173 (3)
O1w—H1w2···O3w	0.84 (3)	1.87 (3)	2.696 (3)	166 (3)
O2w—H2w1···O4^i	0.85 (3)	1.97 (2)	2.793 (4)	165 (4)
O2w—H2w1···O4′^i	0.85 (3)	1.85 (2)	2.671 (10)	162 (4)
O2w—H2w2···O5′^ii	0.85 (3)	2.00 (3)	2.750 (13)	148 (4)
O3w—H3w1···O6^iii	0.84 (3)	1.99 (1)	2.827 (4)	174 (4)
O3w—H3w1···O6′^iii	0.84 (3)	1.98 (3)	2.738 (11)	149 (4)
O3w—H3w2···O2	0.84 (4)	1.99 (4)	2.824 (3)	172 (4)

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