Crystal structure and Hirshfeld surface analysis of di­aqua­bis­(N,N-di­ethyl­nicotinamide-κN¹)bis­(2,4,6-tri­methyl­benzoato-κO)manganese(II)

The Mn^II complex is centrosymmetric and the mol­ecules are linked by O—H...O and C—H...O hydrogen bonds into the three-dimensional supra­molecular network.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.048
• wR factor = 0.144
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.4 Ratio
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C1 Check
PLAT410_ALERT_2_C Short Intra H...H Contact  H19A     ..H17A             1.96 Ang.
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H8B      ..H18E             2.14 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.488 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          5 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          4 Report
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Mn1      --O4        .        5.8 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         8% Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         42 Note
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2018 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          7 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Diaquabis(N,N-diethylnicotinamide-κN¹)bis(2,4,6-trimethylbenzoato-κO)manganese(II)

Crystal data

[Mn(C10H11O2)2(C10H14N2O)2(H2O)2]	F(000) = 822
Mr = 773.83	Dx = 1.233 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9985 reflections
a = 13.1040 (4) Å	θ = 2.5–28.2°
b = 10.8828 (3) Å	µ = 0.37 mm^−1
c = 15.7167 (4) Å	T = 296 K
β = 111.570 (2)°	Block, translucent light colourless
V = 2084.37 (10) Å^3	0.45 × 0.37 × 0.35 mm
Z = 2

Data collection

Bruker SMART BREEZE CCD diffractometer	5178 independent reflections
Radiation source: fine-focus sealed tube	3995 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −17→17
Tmin = 0.851, Tmax = 0.882	k = −14→13
36139 measured reflections	l = −20→20

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) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0696P)^2 + 0.7599P] where P = (Fo^2 + 2Fc^2)/3
5178 reflections	(Δ/σ)max < 0.001
274 parameters	Δρmax = 0.51 e Å^−3
42 restraints	Δρmin = −0.37 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.0000	0.0000	0.0000	0.04559 (14)
O1	−0.14717 (12)	0.04378 (15)	−0.10765 (9)	0.0615 (4)
O2	−0.25400 (18)	−0.1155 (2)	−0.11016 (17)	0.1263 (10)
O3	−0.02706 (15)	0.12536 (14)	0.39218 (9)	0.0699 (4)
O4	0.08409 (16)	0.14917 (14)	−0.04553 (11)	0.0590 (4)
H41	0.058 (2)	0.220 (3)	−0.0636 (19)	0.077 (8)*
H42	0.143 (2)	0.153 (2)	−0.005 (2)	0.075 (9)*
N1	−0.04496 (14)	0.13195 (15)	0.09755 (10)	0.0534 (4)
N2	−0.1788 (2)	0.0256 (3)	0.30478 (15)	0.0975 (8)
C1	−0.23618 (19)	−0.0138 (2)	−0.13796 (16)	0.0667 (6)
C2	−0.32465 (17)	0.0468 (2)	−0.21779 (15)	0.0633 (5)
C3	−0.3318 (2)	0.0191 (2)	−0.30595 (17)	0.0696 (6)
C4	−0.4057 (2)	0.0847 (3)	−0.37831 (17)	0.0805 (7)
H4	−0.4101	0.0677	−0.4375	0.097*
C5	−0.4726 (2)	0.1739 (3)	−0.36515 (19)	0.0837 (8)
C6	−0.4672 (2)	0.1957 (3)	−0.2775 (2)	0.0871 (8)
H6	−0.5142	0.2536	−0.2680	0.104*
C7	−0.3934 (2)	0.1337 (3)	−0.20238 (17)	0.0763 (6)
C8	−0.2595 (3)	−0.0781 (3)	−0.3224 (2)	0.0988 (9)
H8A	−0.2585	−0.0688	−0.3828	0.148*
H8B	−0.2875	−0.1579	−0.3166	0.148*
H8C	−0.1862	−0.0697	−0.2781	0.148*
C9	−0.5484 (3)	0.2479 (4)	−0.4452 (3)	0.1240 (14)
H9A	−0.5621	0.2031	−0.5009	0.186*
H9B	−0.5145	0.3251	−0.4483	0.186*
H9C	−0.6165	0.2623	−0.4370	0.186*
C10	−0.3879 (3)	0.1594 (4)	−0.1064 (2)	0.1176 (12)
H10A	−0.4327	0.2295	−0.1070	0.176*
H10B	−0.3134	0.1760	−0.0676	0.176*
H10C	−0.4143	0.0892	−0.0836	0.176*
C11	−0.0577 (2)	0.2526 (2)	0.08377 (14)	0.0671 (6)
H11	−0.0501	0.2856	0.0319	0.081*
C12	−0.0817 (3)	0.3307 (2)	0.14275 (16)	0.0805 (8)
H12	−0.0887	0.4147	0.1311	0.097*
C13	−0.0952 (2)	0.2834 (2)	0.21932 (14)	0.0661 (6)
H13	−0.1108	0.3345	0.2604	0.079*
C14	−0.08498 (16)	0.15840 (18)	0.23330 (11)	0.0508 (4)
C15	−0.05883 (18)	0.08718 (18)	0.17157 (12)	0.0532 (4)
H15	−0.0504	0.0030	0.1822	0.064*
C16	−0.09574 (19)	0.10153 (18)	0.31679 (12)	0.0580 (5)
C17A	−0.2372 (10)	−0.0494 (10)	0.2202 (6)	0.085 (4)	0.282 (10)
H17A	−0.2608	−0.1285	0.2348	0.102*	0.282 (10)
H17B	−0.1926	−0.0612	0.1835	0.102*	0.282 (10)
C17B	−0.2820 (5)	0.0332 (6)	0.2173 (4)	0.0939 (18)	0.718 (10)
H17C	−0.3462	0.0479	0.2326	0.113*	0.718 (10)
H17D	−0.2752	0.1001	0.1790	0.113*	0.718 (10)
C18A	−0.3339 (15)	0.036 (2)	0.1740 (14)	0.155 (8)	0.282 (10)
H18A	−0.3582	0.0269	0.1089	0.233*	0.282 (10)
H18B	−0.3114	0.1199	0.1902	0.233*	0.282 (10)
H18C	−0.3929	0.0165	0.1940	0.233*	0.282 (10)
C18B	−0.2932 (6)	−0.0862 (6)	0.1678 (5)	0.142 (3)	0.718 (10)
H18D	−0.3531	−0.0811	0.1100	0.213*	0.718 (10)
H18E	−0.3071	−0.1507	0.2038	0.213*	0.718 (10)
H18F	−0.2266	−0.1034	0.1579	0.213*	0.718 (10)
C19	−0.1838 (4)	−0.0419 (4)	0.3858 (2)	0.1213 (14)
H19A	−0.2042	−0.1267	0.3691	0.146*
H19B	−0.1118	−0.0415	0.4342	0.146*
C20	−0.2624 (5)	0.0130 (5)	0.4194 (3)	0.171 (3)
H20A	−0.2656	−0.0343	0.4699	0.257*
H20B	−0.3335	0.0141	0.3713	0.257*
H20C	−0.2402	0.0955	0.4392	0.257*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.0618 (2)	0.0489 (2)	0.02981 (18)	−0.00067 (16)	0.02117 (16)	0.00058 (13)
O1	0.0652 (9)	0.0672 (8)	0.0465 (7)	−0.0039 (7)	0.0140 (6)	0.0079 (6)
O2	0.0932 (14)	0.1235 (18)	0.1255 (18)	−0.0337 (13)	−0.0030 (13)	0.0690 (15)
O3	0.1131 (12)	0.0614 (8)	0.0348 (7)	−0.0133 (8)	0.0266 (7)	−0.0056 (6)
O4	0.0774 (10)	0.0539 (8)	0.0500 (8)	0.0010 (7)	0.0286 (8)	0.0088 (6)
N1	0.0761 (10)	0.0536 (9)	0.0367 (7)	0.0019 (7)	0.0281 (7)	0.0001 (6)
N2	0.127 (2)	0.1230 (19)	0.0551 (12)	−0.0580 (16)	0.0490 (13)	−0.0147 (12)
C1	0.0634 (12)	0.0778 (15)	0.0558 (12)	−0.0048 (10)	0.0184 (10)	0.0167 (10)
C2	0.0560 (11)	0.0751 (13)	0.0557 (11)	−0.0062 (10)	0.0170 (9)	0.0126 (10)
C3	0.0635 (12)	0.0839 (16)	0.0574 (12)	−0.0026 (11)	0.0178 (10)	0.0092 (10)
C4	0.0739 (15)	0.107 (2)	0.0550 (13)	−0.0008 (14)	0.0166 (11)	0.0126 (12)
C5	0.0642 (14)	0.107 (2)	0.0733 (16)	0.0069 (13)	0.0180 (12)	0.0277 (14)
C6	0.0677 (15)	0.105 (2)	0.0923 (19)	0.0159 (14)	0.0339 (14)	0.0174 (16)
C7	0.0677 (13)	0.0976 (18)	0.0669 (14)	−0.0037 (13)	0.0287 (11)	0.0072 (12)
C8	0.117 (2)	0.098 (2)	0.0807 (19)	0.0161 (18)	0.0365 (17)	0.0007 (16)
C9	0.099 (2)	0.162 (4)	0.100 (2)	0.040 (2)	0.0236 (18)	0.059 (2)
C10	0.123 (3)	0.161 (3)	0.080 (2)	0.015 (2)	0.051 (2)	−0.004 (2)
C11	0.1095 (18)	0.0582 (11)	0.0469 (10)	0.0063 (11)	0.0442 (11)	0.0089 (9)
C12	0.143 (2)	0.0507 (11)	0.0622 (13)	0.0147 (13)	0.0547 (15)	0.0080 (10)
C13	0.1038 (17)	0.0565 (11)	0.0481 (10)	0.0091 (11)	0.0397 (11)	−0.0032 (8)
C14	0.0689 (11)	0.0549 (10)	0.0320 (8)	−0.0057 (8)	0.0224 (8)	−0.0043 (7)
C15	0.0819 (13)	0.0471 (9)	0.0360 (8)	0.0005 (9)	0.0280 (8)	−0.0004 (7)
C16	0.0904 (14)	0.0546 (10)	0.0381 (9)	−0.0074 (10)	0.0344 (9)	−0.0077 (7)
C17A	0.129 (9)	0.068 (6)	0.059 (6)	−0.048 (6)	0.037 (5)	−0.022 (4)
C17B	0.098 (4)	0.109 (4)	0.085 (3)	−0.031 (3)	0.046 (3)	−0.017 (3)
C18A	0.121 (12)	0.197 (19)	0.103 (12)	−0.017 (10)	−0.011 (9)	−0.007 (13)
C18B	0.144 (5)	0.143 (5)	0.142 (5)	−0.059 (4)	0.057 (4)	−0.071 (4)
C19	0.183 (4)	0.124 (3)	0.080 (2)	−0.064 (3)	0.077 (2)	−0.0064 (19)
C20	0.164 (4)	0.283 (7)	0.100 (3)	−0.063 (4)	0.088 (3)	−0.019 (3)

Geometric parameters (Å, º)

Mn1—O1	2.0999 (14)	C9—H9C	0.9600
Mn1—O1^i	2.0999 (14)	C10—H10A	0.9600
Mn1—O4	2.2230 (15)	C10—H10B	0.9600
Mn1—O4^i	2.2230 (15)	C10—H10C	0.9600
Mn1—N1	2.3289 (15)	C11—C12	1.377 (3)
Mn1—N1^i	2.3289 (15)	C11—H11	0.9300
O1—C1	1.254 (3)	C12—H12	0.9300
O2—C1	1.243 (3)	C13—C12	1.379 (3)
O3—C16	1.224 (3)	C13—H13	0.9300
O4—H41	0.85 (3)	C14—C13	1.376 (3)
O4—H42	0.80 (3)	C14—C15	1.380 (2)
N1—C11	1.331 (3)	C14—C16	1.504 (2)
N1—C15	1.334 (2)	C15—H15	0.9300
N2—C17A	1.506 (9)	C16—N2	1.324 (3)
N2—C17B	1.536 (7)	C17A—C18A	1.526 (17)
N2—C19	1.493 (3)	C17A—H17A	0.9700
C2—C1	1.511 (3)	C17A—H17B	0.9700
C2—C3	1.387 (3)	C17B—C18B	1.493 (8)
C2—C7	1.388 (4)	C17B—H17C	0.9700
C3—C8	1.505 (4)	C17B—H17D	0.9700
C4—C3	1.390 (3)	C18A—H18A	0.9600
C4—C5	1.373 (4)	C18A—H18B	0.9600
C4—H4	0.9300	C18A—H18C	0.9600
C5—C6	1.373 (4)	C18B—H18D	0.9600
C5—C9	1.516 (4)	C18B—H18E	0.9600
C6—H6	0.9300	C18B—H18F	0.9600
C7—C6	1.395 (4)	C19—C20	1.447 (6)
C7—C10	1.510 (4)	C19—H19A	0.9700
C8—H8A	0.9600	C19—H19B	0.9700
C8—H8B	0.9600	C20—H20A	0.9600
C8—H8C	0.9600	C20—H20B	0.9600
C9—H9A	0.9600	C20—H20C	0.9600
C9—H9B	0.9600
O1···H10B	2.87	C16···H18B	2.80
O1···H13^ii	2.65	C16···H41^v	2.93 (3)
O1···H8C	2.82	C17A···H15	2.78
O2···H42^i	1.90 (3)	C17B···H20B	2.75
O2···H9C^iii	2.48	C18A···H9B^v	2.87
O3···H12^iv	2.85	C18B···H8B^vi	2.79
O3···H11^v	2.52	C18B···H19A	2.97
O3···H41^v	2.00 (3)	C19···H18E	2.97
O3···H19B	2.35	C20···H17C	2.76
O4···H15^i	2.62	H4···H8A	2.37
O4···H11	2.89	H4···H9A	2.38
C1···H10C	2.98	H6···H10A	2.37
C1···H42^i	2.61 (3)	H6···H9C	2.50
C1···H8C	2.59	H8A···H20A^vii	2.31
C1···H10B	2.71	H8B···H17A^viii	2.44
C5···H18B^ii	2.98	H8B···H18E^viii	2.14
C13···H17D	2.97	H11···H41	2.52
C14···H17D	2.40	H15···H18F	2.48
C14···H17B	2.74	H15···H17B	2.00
C14···H18B	2.82	H17A···H19A	1.96
C15···H17D	2.88	H17C···H20B	2.16
C15···H17B	2.44	H18A···H9B^v	2.50
C15···H18F	2.97	H18E···H19A	2.46
O1^i—Mn1—O1	180.00 (7)	H9A—C9—H9B	109.5
O1—Mn1—O4	89.54 (6)	H9A—C9—H9C	109.5
O1^i—Mn1—O4	90.46 (6)	H9B—C9—H9C	109.5
O1—Mn1—O4^i	90.46 (6)	C7—C10—H10A	109.5
O1^i—Mn1—O4^i	89.54 (6)	C7—C10—H10B	109.5
O1—Mn1—N1	90.62 (6)	C7—C10—H10C	109.5
O1^i—Mn1—N1	89.38 (6)	H10A—C10—H10B	109.5
O1—Mn1—N1^i	89.38 (6)	H10A—C10—H10C	109.5
O1^i—Mn1—N1^i	90.62 (6)	H10B—C10—H10C	109.5
O4^i—Mn1—O4	180.00 (9)	N1—C11—C12	123.08 (18)
O4—Mn1—N1	92.12 (6)	N1—C11—H11	118.5
O4^i—Mn1—N1	87.88 (6)	C12—C11—H11	118.5
O4—Mn1—N1^i	87.88 (6)	C11—C12—C13	119.4 (2)
O4^i—Mn1—N1^i	92.12 (6)	C11—C12—H12	120.3
N1—Mn1—N1^i	180.00 (7)	C13—C12—H12	120.3
Mn1—O4—H41	126.1 (18)	C12—C13—H13	120.9
Mn1—O4—H42	103 (2)	C14—C13—C12	118.18 (18)
H41—O4—H42	111 (3)	C14—C13—H13	120.9
C1—O1—Mn1	130.03 (14)	C13—C14—C15	118.53 (17)
C11—N1—Mn1	123.24 (12)	C13—C14—C16	120.74 (16)
C11—N1—C15	116.92 (16)	C15—C14—C16	120.64 (17)
C15—N1—Mn1	119.84 (12)	N1—C15—C14	123.83 (18)
C16—N2—C17A	126.0 (4)	N1—C15—H15	118.1
C16—N2—C17B	120.1 (3)	C14—C15—H15	118.1
C16—N2—C19	118.5 (2)	O3—C16—N2	122.95 (19)
C19—N2—C17A	108.6 (4)	O3—C16—C14	119.10 (19)
C19—N2—C17B	119.3 (3)	N2—C16—C14	117.94 (18)
O1—C1—C2	114.81 (19)	N2—C17A—C18A	98.7 (12)
O2—C1—O1	125.5 (2)	N2—C17A—H17A	112.0
O2—C1—C2	119.7 (2)	N2—C17A—H17B	112.0
C3—C2—C1	118.9 (2)	C18A—C17A—H17A	112.0
C3—C2—C7	120.9 (2)	C18A—C17A—H17B	112.0
C7—C2—C1	120.1 (2)	H17A—C17A—H17B	109.7
C2—C3—C4	118.4 (2)	N2—C17B—H17C	110.1
C2—C3—C8	120.6 (2)	N2—C17B—H17D	110.1
C4—C3—C8	121.0 (2)	C18B—C17B—N2	107.8 (6)
C3—C4—H4	118.9	C18B—C17B—H17C	110.1
C5—C4—C3	122.1 (3)	C18B—C17B—H17D	110.1
C5—C4—H4	118.9	H17C—C17B—H17D	108.5
C4—C5—C6	118.2 (2)	C17B—C18B—H18D	109.5
C4—C5—C9	120.7 (3)	C17B—C18B—H18E	109.5
C6—C5—C9	121.1 (3)	C17B—C18B—H18F	109.5
C5—C6—C7	122.0 (3)	H18D—C18B—H18E	109.5
C5—C6—H6	119.0	H18D—C18B—H18F	109.5
C7—C6—H6	119.0	H18E—C18B—H18F	109.5
C2—C7—C6	118.3 (2)	N2—C19—H19A	109.3
C2—C7—C10	120.4 (3)	N2—C19—H19B	109.3
C6—C7—C10	121.3 (3)	C20—C19—N2	111.6 (4)
C3—C8—H8A	109.5	C20—C19—H19A	109.3
C3—C8—H8B	109.5	C20—C19—H19B	109.3
C3—C8—H8C	109.5	H19A—C19—H19B	108.0
H8A—C8—H8B	109.5	C19—C20—H20A	109.5
H8A—C8—H8C	109.5	C19—C20—H20B	109.5
H8B—C8—H8C	109.5	C19—C20—H20C	109.5
C5—C9—H9A	109.5	H20A—C20—H20B	109.5
C5—C9—H9B	109.5	H20A—C20—H20C	109.5
C5—C9—H9C	109.5	H20B—C20—H20C	109.5
O4—Mn1—O1—C1	168.4 (2)	C1—C2—C3—C8	5.5 (4)
O4^i—Mn1—O1—C1	−11.6 (2)	C7—C2—C3—C4	3.1 (4)
N1—Mn1—O1—C1	−99.5 (2)	C7—C2—C3—C8	−178.0 (2)
N1^i—Mn1—O1—C1	80.5 (2)	C1—C2—C7—C6	174.2 (2)
O1—Mn1—N1—C11	−62.66 (19)	C1—C2—C7—C10	−6.0 (4)
O1^i—Mn1—N1—C11	117.34 (19)	C3—C2—C7—C6	−2.3 (4)
O1—Mn1—N1—C15	117.53 (16)	C3—C2—C7—C10	177.6 (3)
O1^i—Mn1—N1—C15	−62.47 (16)	C5—C4—C3—C2	−1.1 (4)
O4—Mn1—N1—C11	26.91 (19)	C5—C4—C3—C8	−179.9 (3)
O4^i—Mn1—N1—C11	−153.09 (19)	C3—C4—C5—C6	−1.7 (4)
O4—Mn1—N1—C15	−152.91 (16)	C3—C4—C5—C9	177.1 (3)
O4^i—Mn1—N1—C15	27.09 (16)	C4—C5—C6—C7	2.6 (4)
Mn1—O1—C1—O2	−2.5 (4)	C9—C5—C6—C7	−176.2 (3)
Mn1—O1—C1—C2	−179.51 (14)	C2—C7—C6—C5	−0.6 (4)
Mn1—N1—C11—C12	−178.4 (2)	C10—C7—C6—C5	179.5 (3)
C15—N1—C11—C12	1.4 (4)	N1—C11—C12—C13	−1.1 (4)
Mn1—N1—C15—C14	179.68 (16)	C14—C13—C12—C11	−0.6 (4)
C11—N1—C15—C14	−0.1 (3)	C15—C14—C13—C12	1.7 (4)
C16—N2—C17A—C18A	−96.6 (11)	C16—C14—C13—C12	178.3 (2)
C17B—N2—C17A—C18A	−0.4 (10)	C13—C14—C15—N1	−1.5 (3)
C19—N2—C17A—C18A	113.2 (10)	C16—C14—C15—N1	−178.04 (19)
C16—N2—C17B—C18B	117.7 (4)	C13—C14—C16—O3	−65.7 (3)
C17A—N2—C17B—C18B	6.0 (7)	C13—C14—C16—N2	115.6 (3)
C19—N2—C17B—C18B	−78.9 (5)	C15—C14—C16—O3	110.9 (2)
C16—N2—C19—C20	102.2 (4)	C15—C14—C16—N2	−67.9 (3)
C17A—N2—C19—C20	−105.0 (7)	O3—C16—N2—C17A	−152.8 (7)
C17B—N2—C19—C20	−61.5 (5)	O3—C16—N2—C17B	158.4 (3)
C3—C2—C1—O1	89.8 (3)	O3—C16—N2—C19	−5.2 (4)
C3—C2—C1—O2	−87.4 (3)	C14—C16—N2—C17A	26.0 (8)
C7—C2—C1—O1	−86.7 (3)	C14—C16—N2—C17B	−22.9 (4)
C7—C2—C1—O2	96.0 (3)	C14—C16—N2—C19	173.5 (3)
C1—C2—C3—C4	−173.4 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O3^ii	0.85 (3)	2.00 (3)	2.838 (2)	171 (3)
O4—H42···O2^i	0.80 (3)	1.90 (3)	2.660 (3)	157 (3)
C9—H9C···O2^ix	0.96	2.48	3.366 (5)	154
C11—H11···O3^ii	0.93	2.52	3.447 (3)	179

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