Adipatobis(2-phenyl-1H-1,3,7,8-tetra­azacyclo­penta­[l]phenanthrene)manganese(II) dihydrate

In the title compound, [Mn(C₆H₈O₄)(C₁₉H₁₂N₄)₂]·2H₂O, the Mn^II atom is six-coordinated by four N atoms from two bidentate phenanthrene ligands, and two carboxyl­ate O atoms from a bidentate adipate ligand to result in a distorted MnO₂N₄ octa­hedron. Aromatic π–π stacking inter­actions between phenanthrene ligands generate a chain supra­molecular structure that is extended into a three-dimensional network by N—H...O and O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.043
• wR factor = 0.097
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C39
PLAT415_ALERT_2_C Short Inter D-H..H-X       HW21   ..  H8      ..       2.14 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.48
           From the CIF: _reflns_number_total               7481
           Count of symmetry unique reflns         4468
           Completeness (_total/calc)            167.44%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3013
           Fraction of Friedel pairs measured     0.674
           Are heavy atom types Z>Si present        yes

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

   0 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: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Adipatobis(2-phenyl-1H-1,3,7,8,-tetraazacyclopenta[l]phenanthrene)manganese(II) dihydrate

Crystal data

[Mn(C6H8O4)(C19H12N4)2]·2H2O	F(000) = 858
Mr = 827.75	Dx = 1.455 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 14410 reflections
a = 10.884 (2) Å	θ = 3.0–27.5°
b = 17.578 (4) Å	µ = 0.41 mm^−1
c = 11.078 (2) Å	T = 292 K
β = 116.97 (3)°	Block, yellow
V = 1888.9 (8) Å^3	0.33 × 0.31 × 0.29 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID diffractometer	7481 independent reflections
Radiation source: rotorating anode	5726 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 10.0 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −14→14
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −22→19
Tmin = 0.866, Tmax = 0.890	l = −14→14
18684 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0466P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
7481 reflections	Δρmax = 0.36 e Å^−3
545 parameters	Δρmin = −0.24 e Å^−3
8 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.027 (15)

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
C1	0.8824 (3)	−0.1651 (2)	0.3472 (3)	0.0381 (7)
H1	0.7956	−0.1487	0.2840	0.046*
C2	0.9415 (3)	−0.22696 (19)	0.3149 (3)	0.0403 (8)
H2	0.8928	−0.2521	0.2329	0.048*
C3	1.0704 (3)	−0.25089 (18)	0.4030 (3)	0.0343 (7)
H3	1.1119	−0.2911	0.3809	0.041*
C4	1.1394 (3)	−0.21328 (16)	0.5286 (3)	0.0282 (6)
C5	1.0701 (3)	−0.15326 (17)	0.5568 (3)	0.0286 (6)
C6	1.1287 (3)	−0.11748 (16)	0.6884 (3)	0.0284 (6)
C7	1.2576 (3)	−0.13929 (16)	0.7907 (3)	0.0296 (6)
C8	1.3062 (3)	−0.10393 (18)	0.9172 (3)	0.0370 (7)
H8	1.3918	−0.1166	0.9873	0.044*
C9	1.2251 (3)	−0.05022 (18)	0.9358 (4)	0.0404 (8)
H9	1.2546	−0.0266	1.0195	0.048*
C10	1.0993 (3)	−0.03131 (19)	0.8297 (3)	0.0362 (7)
H10	1.0463	0.0057	0.8440	0.043*
C11	1.3294 (3)	−0.19765 (16)	0.7580 (3)	0.0292 (6)
C12	1.2724 (3)	−0.23206 (17)	0.6331 (3)	0.0291 (6)
C13	1.4793 (3)	−0.27773 (17)	0.7616 (3)	0.0313 (6)
C14	1.6062 (3)	−0.32179 (17)	0.8048 (3)	0.0347 (7)
C15	1.6253 (3)	−0.3724 (2)	0.7196 (4)	0.0460 (8)
H15	1.5557	−0.3800	0.6321	0.055*
C16	1.7485 (4)	−0.4122 (2)	0.7645 (4)	0.0501 (9)
H16	1.7604	−0.4464	0.7066	0.060*
C17	1.8527 (4)	−0.4018 (2)	0.8925 (4)	0.0436 (8)
H17	1.9346	−0.4288	0.9212	0.052*
C18	1.8357 (3)	−0.3516 (2)	0.9778 (4)	0.0503 (9)
H18	1.9064	−0.3441	1.0647	0.060*
C19	1.7124 (3)	−0.3118 (2)	0.9344 (4)	0.0473 (9)
H19	1.7011	−0.2780	0.9932	0.057*
C20	0.6427 (3)	0.01063 (19)	0.2198 (4)	0.0435 (8)
H20	0.5958	−0.0275	0.2402	0.052*
C21	0.5784 (3)	0.0449 (2)	0.0919 (4)	0.0465 (9)
H21	0.4907	0.0295	0.0291	0.056*
C22	0.6455 (3)	0.10079 (19)	0.0604 (3)	0.0384 (7)
H22	0.6041	0.1239	−0.0243	0.046*
C23	0.7773 (3)	0.12326 (17)	0.1565 (3)	0.0316 (7)
C24	0.8352 (3)	0.08623 (16)	0.2832 (3)	0.0300 (6)
C25	0.9710 (3)	0.10716 (17)	0.3878 (3)	0.0303 (7)
C26	1.0453 (3)	0.16726 (17)	0.3673 (3)	0.0297 (6)
C27	1.1762 (3)	0.18472 (19)	0.4714 (4)	0.0391 (8)
H27	1.2271	0.2246	0.4616	0.047*
C28	1.0762 (4)	0.3647 (2)	0.0078 (4)	0.0464 (8)
H28	1.1505	0.3536	0.0909	0.056*
C29	1.2281 (3)	0.1423 (2)	0.5877 (4)	0.0446 (8)
H29	1.3148	0.1530	0.6581	0.054*
C30	1.1491 (3)	0.08313 (19)	0.5989 (4)	0.0414 (8)
H30	1.1862	0.0545	0.6781	0.050*
C31	0.9815 (3)	0.20365 (17)	0.2392 (3)	0.0315 (7)
C32	0.8579 (3)	0.18239 (17)	0.1373 (3)	0.0337 (7)
C33	0.9351 (3)	0.27114 (18)	0.0575 (3)	0.0360 (7)
C34	0.9525 (3)	0.32692 (18)	−0.0323 (3)	0.0391 (8)
C35	0.8426 (4)	0.3438 (2)	−0.1566 (4)	0.0483 (9)
H35	0.7586	0.3191	−0.1839	0.058*
C36	0.8581 (4)	0.3974 (2)	−0.2400 (4)	0.0552 (10)
H36	0.7849	0.4077	−0.3243	0.066*
C37	0.9804 (5)	0.4355 (2)	−0.1994 (4)	0.0550 (10)
H37	0.9893	0.4721	−0.2555	0.066*
C38	1.0895 (4)	0.4196 (2)	−0.0765 (4)	0.0539 (10)
H38	1.1724	0.4454	−0.0492	0.065*
C39	0.6607 (3)	−0.11280 (18)	0.5716 (4)	0.0411 (8)
C40	0.5253 (4)	−0.1095 (2)	0.5779 (4)	0.0554 (10)
H40A	0.5350	−0.1365	0.6581	0.066*
H40B	0.4560	−0.1358	0.4997	0.066*
C41	0.4745 (3)	−0.0296 (2)	0.5814 (4)	0.0556 (10)
H41A	0.4770	−0.0008	0.5078	0.067*
H41B	0.3789	−0.0327	0.5639	0.067*
C42	0.5529 (4)	0.0144 (2)	0.7107 (4)	0.0573 (10)
H42A	0.5520	−0.0148	0.7846	0.069*
H42B	0.5040	0.0616	0.7042	0.069*
C43	0.7028 (4)	0.0337 (2)	0.7468 (4)	0.0421 (8)
H43A	0.7436	0.0594	0.8338	0.051*
H43B	0.7529	−0.0134	0.7571	0.051*
C44	0.7229 (3)	0.08340 (19)	0.6449 (3)	0.0362 (7)
N1	1.0508 (2)	−0.06308 (14)	0.7092 (3)	0.0308 (5)
N2	0.9442 (2)	−0.12849 (14)	0.4639 (3)	0.0306 (6)
N3	0.7670 (3)	0.03001 (14)	0.3130 (3)	0.0347 (6)
N4	1.0244 (3)	0.06499 (14)	0.5040 (3)	0.0330 (6)
N5	1.4589 (3)	−0.22687 (14)	0.8390 (3)	0.0332 (6)
N6	1.3695 (2)	−0.28329 (14)	0.6367 (3)	0.0313 (6)
H6	1.3622	−0.3132	0.5723	0.038*
N7	1.0301 (3)	0.26064 (14)	0.1888 (3)	0.0345 (6)
H7	1.1061	0.2852	0.2316	0.041*
N8	0.8264 (3)	0.22409 (15)	0.0212 (3)	0.0353 (6)
O1	0.6751 (2)	−0.06818 (15)	0.4900 (3)	0.0504 (6)
O2	0.7485 (3)	−0.15819 (19)	0.6454 (3)	0.0774 (10)
O1W	0.5706 (3)	0.21343 (18)	0.7745 (3)	0.0625 (7)
O3	0.8266 (2)	0.07036 (13)	0.6256 (3)	0.0489 (6)
O2W	0.4099 (3)	0.2975 (3)	0.8694 (4)	0.1015 (13)
O4	0.6416 (2)	0.13705 (13)	0.5900 (2)	0.0440 (6)
Mn1	0.86558 (4)	−0.02155 (3)	0.52329 (5)	0.03242 (12)
HW11	0.659 (2)	0.215 (3)	0.845 (3)	0.076 (14)*
HW12	0.579 (4)	0.188 (3)	0.708 (3)	0.114*
HW21	0.462 (4)	0.292 (3)	0.951 (2)	0.114*
HW22	0.462 (4)	0.3023 (17)	0.821 (4)	0.114*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0313 (16)	0.0409 (18)	0.0341 (19)	0.0015 (14)	0.0076 (15)	−0.0020 (15)
C2	0.0464 (19)	0.0361 (18)	0.0352 (19)	−0.0033 (15)	0.0158 (17)	−0.0081 (15)
C3	0.0389 (17)	0.0316 (17)	0.0315 (18)	0.0031 (14)	0.0152 (15)	−0.0028 (13)
C4	0.0337 (15)	0.0213 (14)	0.0337 (17)	−0.0024 (12)	0.0188 (14)	0.0015 (12)
C5	0.0300 (15)	0.0267 (15)	0.0304 (17)	−0.0012 (12)	0.0149 (14)	0.0006 (12)
C6	0.0347 (15)	0.0216 (14)	0.0326 (17)	0.0023 (12)	0.0184 (14)	0.0029 (12)
C7	0.0314 (15)	0.0266 (15)	0.0303 (17)	0.0000 (12)	0.0134 (14)	−0.0014 (12)
C8	0.0363 (16)	0.0392 (18)	0.0289 (18)	−0.0010 (14)	0.0090 (14)	−0.0057 (14)
C9	0.0457 (18)	0.0393 (18)	0.039 (2)	0.0006 (14)	0.0213 (17)	−0.0065 (14)
C10	0.0431 (16)	0.0309 (18)	0.0414 (18)	0.0017 (15)	0.0251 (15)	−0.0034 (15)
C11	0.0320 (15)	0.0249 (14)	0.0293 (17)	0.0007 (12)	0.0127 (13)	−0.0008 (12)
C12	0.0310 (15)	0.0252 (15)	0.0325 (17)	0.0008 (13)	0.0155 (14)	0.0016 (12)
C13	0.0280 (14)	0.0329 (16)	0.0333 (18)	0.0019 (13)	0.0142 (14)	0.0004 (13)
C14	0.0316 (15)	0.0311 (16)	0.041 (2)	0.0021 (13)	0.0161 (15)	0.0056 (14)
C15	0.0443 (18)	0.049 (2)	0.041 (2)	0.0119 (17)	0.0162 (17)	−0.0017 (16)
C16	0.055 (2)	0.044 (2)	0.056 (3)	0.0146 (17)	0.029 (2)	−0.0019 (18)
C17	0.0395 (18)	0.0374 (19)	0.056 (2)	0.0087 (15)	0.0237 (19)	0.0104 (17)
C18	0.0368 (18)	0.046 (2)	0.054 (2)	0.0091 (16)	0.0084 (17)	0.0001 (18)
C19	0.0401 (18)	0.043 (2)	0.049 (2)	0.0071 (16)	0.0116 (17)	−0.0103 (16)
C20	0.0349 (17)	0.0392 (18)	0.055 (2)	−0.0059 (14)	0.0193 (18)	0.0045 (16)
C21	0.0363 (17)	0.048 (2)	0.043 (2)	−0.0098 (15)	0.0078 (17)	0.0036 (16)
C22	0.0361 (16)	0.0370 (18)	0.0357 (19)	0.0006 (14)	0.0106 (15)	0.0024 (14)
C23	0.0313 (14)	0.0293 (16)	0.0352 (18)	0.0007 (13)	0.0161 (14)	−0.0020 (13)
C24	0.0364 (16)	0.0215 (14)	0.0370 (18)	0.0013 (13)	0.0208 (15)	0.0014 (13)
C25	0.0326 (16)	0.0269 (15)	0.0355 (18)	0.0002 (13)	0.0190 (14)	−0.0040 (13)
C26	0.0331 (16)	0.0281 (15)	0.0301 (17)	−0.0029 (13)	0.0162 (14)	−0.0054 (13)
C27	0.0386 (17)	0.0378 (19)	0.043 (2)	−0.0070 (15)	0.0207 (16)	−0.0037 (15)
C28	0.058 (2)	0.042 (2)	0.046 (2)	−0.0063 (17)	0.0299 (19)	−0.0010 (16)
C29	0.0361 (17)	0.048 (2)	0.043 (2)	−0.0018 (16)	0.0120 (17)	0.0012 (17)
C30	0.0378 (18)	0.0417 (19)	0.041 (2)	0.0000 (15)	0.0143 (16)	0.0070 (16)
C31	0.0371 (16)	0.0263 (15)	0.0359 (19)	−0.0011 (13)	0.0208 (15)	−0.0008 (13)
C32	0.0382 (16)	0.0294 (16)	0.0372 (19)	−0.0035 (13)	0.0202 (15)	0.0009 (13)
C33	0.0455 (18)	0.0281 (15)	0.0397 (19)	0.0010 (14)	0.0238 (16)	−0.0010 (14)
C34	0.055 (2)	0.0278 (16)	0.045 (2)	−0.0004 (15)	0.0316 (18)	−0.0023 (14)
C35	0.054 (2)	0.045 (2)	0.050 (2)	0.0045 (18)	0.028 (2)	0.0067 (18)
C36	0.074 (3)	0.044 (2)	0.054 (2)	0.008 (2)	0.034 (2)	0.0119 (18)
C37	0.086 (3)	0.0338 (19)	0.068 (3)	0.004 (2)	0.055 (3)	0.0099 (18)
C38	0.072 (3)	0.039 (2)	0.068 (3)	−0.0133 (19)	0.047 (2)	−0.0037 (19)
C39	0.0431 (18)	0.0300 (17)	0.048 (2)	0.0037 (15)	0.0190 (17)	−0.0021 (15)
C40	0.050 (2)	0.045 (2)	0.080 (3)	−0.0009 (18)	0.037 (2)	0.010 (2)
C41	0.0395 (17)	0.050 (2)	0.087 (3)	−0.0011 (19)	0.0369 (19)	−0.002 (2)
C42	0.068 (3)	0.053 (2)	0.070 (3)	0.001 (2)	0.049 (2)	0.006 (2)
C43	0.0499 (19)	0.0356 (18)	0.041 (2)	0.0061 (15)	0.0204 (17)	0.0052 (15)
C44	0.0390 (17)	0.0319 (17)	0.0390 (19)	−0.0003 (15)	0.0188 (16)	−0.0030 (15)
N1	0.0356 (13)	0.0258 (13)	0.0330 (15)	0.0008 (11)	0.0174 (12)	−0.0007 (11)
N2	0.0321 (13)	0.0281 (13)	0.0316 (15)	0.0011 (11)	0.0143 (12)	0.0003 (11)
N3	0.0358 (13)	0.0288 (13)	0.0400 (16)	−0.0019 (11)	0.0175 (13)	0.0037 (12)
N4	0.0334 (14)	0.0308 (14)	0.0356 (16)	0.0021 (12)	0.0164 (13)	0.0014 (12)
N5	0.0351 (13)	0.0313 (14)	0.0325 (14)	0.0040 (11)	0.0146 (12)	−0.0002 (11)
N6	0.0339 (13)	0.0284 (13)	0.0338 (15)	0.0013 (10)	0.0171 (12)	−0.0039 (11)
N7	0.0426 (14)	0.0266 (13)	0.0388 (16)	−0.0058 (11)	0.0225 (14)	−0.0017 (11)
N8	0.0375 (14)	0.0343 (14)	0.0356 (16)	−0.0008 (12)	0.0178 (13)	0.0038 (12)
O1	0.0448 (13)	0.0536 (15)	0.0591 (17)	−0.0087 (12)	0.0290 (13)	0.0023 (13)
O2	0.078 (2)	0.070 (2)	0.069 (2)	0.0405 (18)	0.0188 (17)	0.0146 (17)
O1W	0.0544 (17)	0.072 (2)	0.0555 (19)	0.0048 (14)	0.0196 (16)	−0.0074 (15)
O3	0.0529 (14)	0.0353 (13)	0.0735 (19)	−0.0010 (11)	0.0418 (15)	−0.0086 (12)
O2W	0.060 (2)	0.171 (4)	0.056 (2)	0.020 (2)	0.0115 (18)	0.013 (2)
O4	0.0498 (13)	0.0434 (14)	0.0431 (15)	0.0105 (12)	0.0247 (12)	0.0103 (11)
Mn1	0.0330 (2)	0.0286 (2)	0.0384 (3)	0.0034 (2)	0.0186 (2)	0.0034 (2)

Geometric parameters (Å, º)

C1—N2	1.322 (4)	C27—C29	1.369 (5)
C1—C2	1.390 (5)	C27—H27	0.9300
C1—H1	0.9300	C28—C34	1.382 (5)
C2—C3	1.362 (4)	C28—C38	1.394 (5)
C2—H2	0.9300	C28—H28	0.9300
C3—C4	1.410 (4)	C29—C30	1.391 (5)
C3—H3	0.9300	C29—H29	0.9300
C4—C5	1.413 (4)	C30—N4	1.325 (4)
C4—C12	1.422 (4)	C30—H30	0.9300
C5—N2	1.359 (4)	C31—C32	1.359 (4)
C5—C6	1.444 (4)	C31—N7	1.365 (4)
C6—N1	1.365 (4)	C32—N8	1.382 (4)
C6—C7	1.399 (4)	C33—N8	1.346 (4)
C7—C8	1.399 (4)	C33—N7	1.362 (4)
C7—C11	1.432 (4)	C33—C34	1.469 (4)
C8—C9	1.370 (4)	C34—C35	1.386 (5)
C8—H8	0.9300	C35—C36	1.382 (5)
C9—C10	1.381 (5)	C35—H35	0.9300
C9—H9	0.9300	C36—C37	1.371 (5)
C10—N1	1.316 (4)	C36—H36	0.9300
C10—H10	0.9300	C37—C38	1.370 (6)
C11—C12	1.374 (4)	C37—H37	0.9300
C11—N5	1.382 (4)	C38—H38	0.9300
C12—N6	1.375 (4)	C39—O2	1.229 (4)
C13—N5	1.325 (4)	C39—O1	1.259 (4)
C13—N6	1.361 (4)	C39—C40	1.508 (4)
C13—C14	1.462 (4)	C40—C41	1.516 (5)
C14—C15	1.381 (5)	C40—H40A	0.9700
C14—C19	1.387 (5)	C40—H40B	0.9700
C15—C16	1.388 (5)	C41—C42	1.506 (6)
C15—H15	0.9300	C41—H41A	0.9700
C16—C17	1.368 (5)	C41—H41B	0.9700
C16—H16	0.9300	C42—C43	1.532 (5)
C17—C18	1.366 (5)	C42—H42A	0.9700
C17—H17	0.9300	C42—H42B	0.9700
C18—C19	1.391 (4)	C43—C44	1.519 (4)
C18—H18	0.9300	C43—H43A	0.9700
C19—H19	0.9300	C43—H43B	0.9700
C20—N3	1.321 (4)	C44—O4	1.246 (4)
C20—C21	1.401 (5)	C44—O3	1.262 (4)
C20—H20	0.9300	Mn1—N1	2.252 (3)
C21—C22	1.361 (4)	Mn1—N2	2.283 (2)
C21—H21	0.9300	Mn1—N3	2.266 (3)
C22—C23	1.401 (4)	Mn1—N4	2.384 (2)
C22—H22	0.9300	N6—H6	0.8600
C23—C24	1.410 (4)	N7—H7	0.8600
C23—C32	1.437 (4)	Mn1—O1	2.101 (2)
C24—N3	1.363 (4)	O1W—HW11	0.926 (18)
C24—C25	1.453 (4)	O1W—HW12	0.90 (4)
C25—N4	1.366 (4)	Mn1—O3	2.123 (2)
C25—C26	1.410 (4)	O2W—HW21	0.828 (19)
C26—C27	1.401 (5)	O2W—HW22	0.94 (5)
C26—C31	1.419 (4)
N2—C1—C2	122.8 (3)	N7—C31—C26	129.4 (3)
N2—C1—H1	118.6	C31—C32—N8	111.1 (3)
C2—C1—H1	118.6	C31—C32—C23	121.2 (3)
C3—C2—C1	120.2 (3)	N8—C32—C23	127.7 (3)
C3—C2—H2	119.9	N8—C33—N7	112.0 (3)
C1—C2—H2	119.9	N8—C33—C34	125.0 (3)
C2—C3—C4	118.5 (3)	N7—C33—C34	123.0 (3)
C2—C3—H3	120.7	C28—C34—C35	119.5 (3)
C4—C3—H3	120.7	C28—C34—C33	120.6 (3)
C3—C4—C5	118.0 (3)	C35—C34—C33	119.9 (3)
C3—C4—C12	125.8 (3)	C36—C35—C34	119.9 (4)
C5—C4—C12	116.2 (3)	C36—C35—H35	120.1
N2—C5—C4	121.9 (3)	C34—C35—H35	120.1
N2—C5—C6	117.2 (2)	C37—C36—C35	120.5 (4)
C4—C5—C6	120.9 (3)	C37—C36—H36	119.7
N1—C6—C7	121.8 (3)	C35—C36—H36	119.7
N1—C6—C5	116.9 (3)	C38—C37—C36	120.1 (3)
C7—C6—C5	121.3 (2)	C38—C37—H37	120.0
C6—C7—C8	118.3 (3)	C36—C37—H37	120.0
C6—C7—C11	116.9 (3)	C37—C38—C28	120.0 (4)
C8—C7—C11	124.7 (3)	C37—C38—H38	120.0
C9—C8—C7	118.7 (3)	C28—C38—H38	120.0
C9—C8—H8	120.7	O2—C39—O1	124.7 (3)
C7—C8—H8	120.7	O2—C39—C40	118.4 (4)
C8—C9—C10	119.7 (3)	O1—C39—C40	116.8 (3)
C8—C9—H9	120.2	C39—C40—C41	114.3 (3)
C10—C9—H9	120.2	C39—C40—H40A	108.7
N1—C10—C9	123.3 (3)	C41—C40—H40A	108.7
N1—C10—H10	118.4	C39—C40—H40B	108.7
C9—C10—H10	118.4	C41—C40—H40B	108.7
C12—C11—N5	110.6 (2)	H40A—C40—H40B	107.6
C12—C11—C7	121.4 (3)	C42—C41—C40	116.4 (3)
N5—C11—C7	128.0 (3)	C42—C41—H41A	108.2
C11—C12—N6	105.6 (3)	C40—C41—H41A	108.2
C11—C12—C4	123.1 (3)	C42—C41—H41B	108.2
N6—C12—C4	131.3 (3)	C40—C41—H41B	108.2
N5—C13—N6	112.3 (2)	H41A—C41—H41B	107.4
N5—C13—C14	123.8 (3)	C41—C42—C43	116.0 (3)
N6—C13—C14	124.0 (3)	C41—C42—H42A	108.3
C15—C14—C19	118.4 (3)	C43—C42—H42A	108.3
C15—C14—C13	122.1 (3)	C41—C42—H42B	108.3
C19—C14—C13	119.5 (3)	C43—C42—H42B	108.3
C14—C15—C16	120.0 (3)	H42A—C42—H42B	107.4
C14—C15—H15	120.0	C44—C43—C42	115.4 (3)
C16—C15—H15	120.0	C44—C43—H43A	108.4
C17—C16—C15	121.1 (3)	C42—C43—H43A	108.4
C17—C16—H16	119.5	C44—C43—H43B	108.4
C15—C16—H16	119.5	C42—C43—H43B	108.4
C18—C17—C16	119.7 (3)	H43A—C43—H43B	107.5
C18—C17—H17	120.2	O4—C44—O3	123.1 (3)
C16—C17—H17	120.2	O4—C44—C43	119.2 (3)
C17—C18—C19	119.8 (4)	O3—C44—C43	117.6 (3)
C17—C18—H18	120.1	C10—N1—C6	118.3 (3)
C19—C18—H18	120.1	C10—N1—Mn1	124.8 (2)
C14—C19—C18	121.0 (3)	C6—N1—Mn1	116.06 (19)
C14—C19—H19	119.5	C1—N2—C5	118.4 (3)
C18—C19—H19	119.5	C1—N2—Mn1	126.2 (2)
N3—C20—C21	123.0 (3)	C5—N2—Mn1	115.23 (19)
N3—C20—H20	118.5	C20—N3—C24	118.4 (3)
C21—C20—H20	118.5	C20—N3—Mn1	122.7 (2)
C22—C21—C20	119.3 (3)	C24—N3—Mn1	118.9 (2)
C22—C21—H21	120.3	C30—N4—C25	117.5 (3)
C20—C21—H21	120.3	C30—N4—Mn1	127.3 (2)
C21—C22—C23	119.5 (3)	C25—N4—Mn1	114.5 (2)
C21—C22—H22	120.2	C13—N5—C11	104.6 (3)
C23—C22—H22	120.2	C13—N6—C12	107.0 (2)
C22—C23—C24	117.9 (3)	C13—N6—H6	126.5
C22—C23—C32	125.1 (3)	C12—N6—H6	126.5
C24—C23—C32	117.0 (3)	C33—N7—C31	106.8 (3)
N3—C24—C23	121.9 (3)	C33—N7—H7	126.6
N3—C24—C25	117.3 (3)	C31—N7—H7	126.6
C23—C24—C25	120.7 (3)	C33—N8—C32	103.6 (3)
N4—C25—C26	121.9 (3)	C39—O1—Mn1	123.5 (2)
N4—C25—C24	117.3 (3)	HW11—O1W—HW12	105 (2)
C26—C25—C24	120.8 (3)	C44—O3—Mn1	129.7 (2)
C27—C26—C25	118.3 (3)	HW21—O2W—HW22	110 (3)
C27—C26—C31	125.4 (3)	O1—Mn1—O3	88.31 (9)
C25—C26—C31	116.2 (3)	O1—Mn1—N1	115.89 (9)
C29—C27—C26	119.2 (3)	O3—Mn1—N1	94.07 (10)
C29—C27—H27	120.4	O1—Mn1—N3	90.35 (10)
C26—C27—H27	120.4	O3—Mn1—N3	97.37 (10)
C34—C28—C38	120.0 (4)	N1—Mn1—N3	151.67 (8)
C34—C28—H28	120.0	O1—Mn1—N2	95.59 (9)
C38—C28—H28	120.0	O3—Mn1—N2	166.44 (10)
C27—C29—C30	118.9 (3)	N1—Mn1—N2	72.53 (9)
C27—C29—H29	120.6	N3—Mn1—N2	95.59 (9)
C30—C29—H29	120.6	O1—Mn1—N4	158.64 (9)
N4—C30—C29	124.1 (3)	O3—Mn1—N4	83.73 (9)
N4—C30—H30	117.9	N1—Mn1—N4	84.51 (9)
C29—C30—H30	117.9	N3—Mn1—N4	71.16 (9)
C32—C31—N7	106.5 (3)	N2—Mn1—N4	96.75 (9)
C32—C31—C26	123.9 (3)
N2—C1—C2—C3	−2.3 (5)	C9—C10—N1—C6	0.1 (4)
C1—C2—C3—C4	2.2 (5)	C9—C10—N1—Mn1	−169.0 (2)
C2—C3—C4—C5	0.8 (4)	C7—C6—N1—C10	−0.5 (4)
C2—C3—C4—C12	178.4 (3)	C5—C6—N1—C10	177.7 (3)
C3—C4—C5—N2	−4.1 (4)	C7—C6—N1—Mn1	169.5 (2)
C12—C4—C5—N2	178.1 (3)	C5—C6—N1—Mn1	−12.2 (3)
C3—C4—C5—C6	173.6 (3)	C2—C1—N2—C5	−1.0 (5)
C12—C4—C5—C6	−4.2 (4)	C2—C1—N2—Mn1	175.4 (2)
N2—C5—C6—N1	1.6 (4)	C4—C5—N2—C1	4.2 (4)
C4—C5—C6—N1	−176.2 (2)	C6—C5—N2—C1	−173.6 (3)
N2—C5—C6—C7	179.9 (3)	C4—C5—N2—Mn1	−172.6 (2)
C4—C5—C6—C7	2.0 (4)	C6—C5—N2—Mn1	9.6 (3)
N1—C6—C7—C8	0.2 (4)	C21—C20—N3—C24	0.4 (5)
C5—C6—C7—C8	−178.0 (3)	C21—C20—N3—Mn1	176.8 (3)
N1—C6—C7—C11	179.2 (2)	C23—C24—N3—C20	−0.5 (4)
C5—C6—C7—C11	1.0 (4)	C25—C24—N3—C20	179.3 (3)
C6—C7—C8—C9	0.6 (4)	C23—C24—N3—Mn1	−177.1 (2)
C11—C7—C8—C9	−178.3 (3)	C25—C24—N3—Mn1	2.7 (3)
C7—C8—C9—C10	−1.1 (5)	C29—C30—N4—C25	0.3 (5)
C8—C9—C10—N1	0.7 (5)	C29—C30—N4—Mn1	−169.8 (2)
C6—C7—C11—C12	−1.8 (4)	C26—C25—N4—C30	0.9 (4)
C8—C7—C11—C12	177.2 (3)	C24—C25—N4—C30	179.0 (3)
C6—C7—C11—N5	177.5 (3)	C26—C25—N4—Mn1	172.3 (2)
C8—C7—C11—N5	−3.6 (5)	C24—C25—N4—Mn1	−9.6 (3)
N5—C11—C12—N6	−0.5 (3)	N6—C13—N5—C11	−0.8 (3)
C7—C11—C12—N6	178.9 (2)	C14—C13—N5—C11	178.2 (3)
N5—C11—C12—C4	−179.9 (3)	C12—C11—N5—C13	0.8 (3)
C7—C11—C12—C4	−0.6 (4)	C7—C11—N5—C13	−178.5 (3)
C3—C4—C12—C11	−174.1 (3)	N5—C13—N6—C12	0.6 (3)
C5—C4—C12—C11	3.5 (4)	C14—C13—N6—C12	−178.5 (3)
C3—C4—C12—N6	6.6 (5)	C11—C12—N6—C13	0.0 (3)
C5—C4—C12—N6	−175.8 (3)	C4—C12—N6—C13	179.4 (3)
N5—C13—C14—C15	−177.8 (3)	N8—C33—N7—C31	0.7 (3)
N6—C13—C14—C15	1.1 (5)	C34—C33—N7—C31	−178.5 (3)
N5—C13—C14—C19	1.0 (5)	C32—C31—N7—C33	−0.8 (3)
N6—C13—C14—C19	179.9 (3)	C26—C31—N7—C33	175.0 (3)
C19—C14—C15—C16	0.2 (5)	N7—C33—N8—C32	−0.2 (3)
C13—C14—C15—C16	179.0 (3)	C34—C33—N8—C32	178.9 (3)
C14—C15—C16—C17	−0.3 (6)	C31—C32—N8—C33	−0.3 (3)
C15—C16—C17—C18	0.0 (6)	C23—C32—N8—C33	−180.0 (3)
C16—C17—C18—C19	0.4 (5)	O2—C39—O1—Mn1	−31.3 (5)
C15—C14—C19—C18	0.2 (5)	C40—C39—O1—Mn1	148.6 (3)
C13—C14—C19—C18	−178.6 (3)	O4—C44—O3—Mn1	−111.4 (3)
C17—C18—C19—C14	−0.5 (5)	C43—C44—O3—Mn1	72.4 (4)
N3—C20—C21—C22	0.0 (5)	C39—O1—Mn1—O3	−89.1 (3)
C20—C21—C22—C23	−0.2 (5)	C39—O1—Mn1—N1	4.6 (3)
C21—C22—C23—C24	0.1 (5)	C39—O1—Mn1—N3	173.5 (3)
C21—C22—C23—C32	−178.7 (3)	C39—O1—Mn1—N2	77.8 (3)
C22—C23—C24—N3	0.3 (4)	C39—O1—Mn1—N4	−157.1 (3)
C32—C23—C24—N3	179.1 (3)	C44—O3—Mn1—O1	−1.9 (3)
C22—C23—C24—C25	−179.5 (3)	C44—O3—Mn1—N1	−117.7 (3)
C32—C23—C24—C25	−0.7 (4)	C44—O3—Mn1—N3	88.3 (3)
N3—C24—C25—N4	4.9 (4)	C44—O3—Mn1—N2	−108.9 (4)
C23—C24—C25—N4	−175.3 (3)	C44—O3—Mn1—N4	158.3 (3)
N3—C24—C25—C26	−176.9 (3)	C10—N1—Mn1—O1	−90.4 (2)
C23—C24—C25—C26	2.9 (4)	C6—N1—Mn1—O1	100.3 (2)
N4—C25—C26—C27	−1.6 (4)	C10—N1—Mn1—O3	−0.3 (2)
C24—C25—C26—C27	−179.7 (3)	C6—N1—Mn1—O3	−169.61 (19)
N4—C25—C26—C31	176.5 (3)	C10—N1—Mn1—N3	113.5 (3)
C24—C25—C26—C31	−1.6 (4)	C6—N1—Mn1—N3	−55.8 (3)
C25—C26—C27—C29	1.1 (4)	C10—N1—Mn1—N2	−178.1 (2)
C31—C26—C27—C29	−176.7 (3)	C6—N1—Mn1—N2	12.54 (18)
C26—C27—C29—C30	0.0 (5)	C10—N1—Mn1—N4	83.0 (2)
C27—C29—C30—N4	−0.7 (5)	C6—N1—Mn1—N4	−86.3 (2)
C27—C26—C31—C32	175.9 (3)	C20—N3—Mn1—O1	−12.9 (3)
C25—C26—C31—C32	−1.9 (4)	C24—N3—Mn1—O1	163.5 (2)
C27—C26—C31—N7	0.8 (5)	C20—N3—Mn1—O3	−101.2 (3)
C25—C26—C31—N7	−177.1 (3)	C24—N3—Mn1—O3	75.2 (2)
N7—C31—C32—N8	0.7 (3)	C20—N3—Mn1—N1	145.8 (2)
C26—C31—C32—N8	−175.4 (3)	C24—N3—Mn1—N1	−37.8 (3)
N7—C31—C32—C23	−179.6 (3)	C20—N3—Mn1—N2	82.8 (3)
C26—C31—C32—C23	4.3 (5)	C24—N3—Mn1—N2	−100.8 (2)
C22—C23—C32—C31	175.9 (3)	C20—N3—Mn1—N4	178.0 (3)
C24—C23—C32—C31	−2.8 (4)	C24—N3—Mn1—N4	−5.6 (2)
C22—C23—C32—N8	−4.5 (5)	C1—N2—Mn1—O1	56.5 (3)
C24—C23—C32—N8	176.8 (3)	C5—N2—Mn1—O1	−127.0 (2)
C38—C28—C34—C35	0.2 (5)	C1—N2—Mn1—O3	162.7 (3)
C38—C28—C34—C33	−177.6 (3)	C5—N2—Mn1—O3	−20.8 (5)
N8—C33—C34—C28	−170.4 (3)	C1—N2—Mn1—N1	171.9 (3)
N7—C33—C34—C28	8.7 (5)	C5—N2—Mn1—N1	−11.60 (18)
N8—C33—C34—C35	11.8 (5)	C1—N2—Mn1—N3	−34.4 (3)
N7—C33—C34—C35	−169.1 (3)	C5—N2—Mn1—N3	142.09 (19)
C28—C34—C35—C36	0.9 (5)	C1—N2—Mn1—N4	−106.1 (3)
C33—C34—C35—C36	178.7 (3)	C5—N2—Mn1—N4	70.5 (2)
C34—C35—C36—C37	−1.6 (5)	C30—N4—Mn1—O1	147.1 (3)
C35—C36—C37—C38	1.2 (6)	C25—N4—Mn1—O1	−23.3 (4)
C36—C37—C38—C28	−0.1 (5)	C30—N4—Mn1—O3	78.3 (3)
C34—C28—C38—C37	−0.6 (5)	C25—N4—Mn1—O3	−92.1 (2)
O2—C39—C40—C41	135.4 (4)	C30—N4—Mn1—N1	−16.4 (3)
O1—C39—C40—C41	−44.5 (5)	C25—N4—Mn1—N1	173.2 (2)
C39—C40—C41—C42	−71.3 (4)	C30—N4—Mn1—N3	178.3 (3)
C40—C41—C42—C43	65.0 (4)	C25—N4—Mn1—N3	7.95 (19)
C41—C42—C43—C44	61.3 (5)	C30—N4—Mn1—N2	−88.0 (3)
C42—C43—C44—O4	39.9 (5)	C25—N4—Mn1—N2	101.6 (2)
C42—C43—C44—O3	−143.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—HW12···O4	0.90 (4)	1.95 (2)	2.830 (4)	167 (4)
O1W—HW11···N8^i	0.93 (2)	1.98 (2)	2.891 (4)	167 (3)
O2W—HW22···O1W	0.94 (5)	2.16 (4)	2.831 (5)	127 (2)
O2W—HW21···N5^ii	0.83 (2)	2.11 (2)	2.911 (5)	164 (4)
N6—H6···O4^iii	0.86	1.98	2.830 (3)	168

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