fac-Bromido/chlorido­(0.50/0.50)[3-carbamoyl-1-(1,10-phenanthrolin-2-ylmeth­yl)pyridinium-κ2N,N′]tri­carbonyl­manganese(I) 0.49-bromide 0.51-chloride methanol monosolvate

Wadayama, K.; Takase, T.; Oyama, D.

doi:10.1107/S2414314618017923

fac-Bromido/chlorido(0.50/0.50)[3-carbamoyl-1-(1,10-phenanthrolin-2-ylmethyl)pyridinium-κ²N,N′]tricarbonylmanganese(I) 0.49-bromide 0.51-chloride methanol monosolvate

The title complex, [MnBr_0.50Cl_0.50(C₁₉H₁₅N₄O)(CO)₃]Br_0.49Cl_0.51·CH₃OH, exhibits substitutional disorder of the halogen ligand in the asymmetric unit, with almost the same occupancies for Br and Cl. The Mn^I atom is coordinated in a distorted octahedral environment by three carbonyl C atoms, the disordered X⁻ ligand (X = Br or Cl) and two N atoms from the 1,10-phenanthroline ligand bearing a nicotinamide pendant moiety. The cation displays a fac configuration of the carbonyl ligands. There is another disorder between the chloride ligand and its trans-situated carbonyl ligand, and between Cl⁻ and Br⁻ at the position of the counter-anion. In the crystal, intermolecular C—H

X, N—H

X, O—H

X (X = Br or Cl) and C—H

O hydrogen bonds lead to the formation of a three-dimensional network.

Keywords: crystal structure; manganese complex; phenanthroline derivative; substitutional disorder; NAD-mimic ligand; carbonyl; hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314618017923/wm4091sup1.cif Contains datablocks General, I
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314618017923/wm4091Isup2.hkl Contains datablock I
	MDL mol file https://doi.org/10.1107/S2414314618017923/wm4091Isup3.mol Supplementary material

CCDC reference: 1885987

checkCIF report

Key indicators

Single-crystal X-ray study
T = 93 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R factor = 0.038
wR factor = 0.088
Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check
PLAT077_ALERT_4_C Unitcell Contains Non-integer Number of Atoms ..     Please Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.662 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          7 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         17 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          4 Note

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C23 H19 Br1 Cl1 Mn1 N4 O5
            Atom count from the _atom_site data:  C23 H19 Br1 Cl1.014099 Mn1 N4
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          3 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT068_ALERT_1_G Reported F000 Differs from Calcd (or Missing)...     Please Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)     0.0008 Degree
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Br1B     --Mn1      .       13.4 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Mn1      --Cl1E     .       13.0 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Mn1      --Cl3D     .       13.2 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Mn1      --C2       .        5.7 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Mn1      --C30D     .       15.1 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         9% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  4  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  1         47.01 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  3          0.49 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  4          0.51 Check
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         38 Check
              CL3D -O1C  -C1C     1.555   1.555   1.555             12.50 Deg.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT882_ALERT_1_G No Datum for _diffrn_reflns_av_unetI/netI ......     Please Do !
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         46 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

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

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

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: CrystalStructure (Rigaku, 2010), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

fac-Bromido/chlorido(0.50/0.50)[3-carbamoyl-1-(1,10-phenanthrolin-2-ylmethyl)pyridinium-κ²N,N']tricarbonylmanganese(I) 0.49-bromide 0.51-chloride methanol monosolvate top

Crystal data top

[MnBr_0.50Cl_0.50(C₁₉H₁₅N₄O)(CO)₃]Br_0.49Cl_0.51·CH₄O	Z = 2
M_r = 601.72	F(000) = 604.00
Triclinic, P1	D_x = 1.678 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 7.9489 (2) Å	Cell parameters from 11817 reflections
b = 9.3587 (3) Å	θ = 3.2–27.5°
c = 16.6744 (5) Å	µ = 2.39 mm⁻¹
α = 87.3910 (8)°	T = 93 K
β = 76.4891 (8)°	Prism, yellow
γ = 80.8427 (8)°	0.20 × 0.15 × 0.05 mm
V = 1190.69 (6) Å³

Data collection top

Rigaku Saturn70 diffractometer	5073 reflections with F² > 2.0σ(F²)
Detector resolution: 29.257 pixels mm^-1	R_int = 0.017
ω scans	θ_max = 27.5°
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	h = −10→10
T_min = 0.517, T_max = 0.620	k = −12→12
12472 measured reflections	l = −21→21
5395 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0244P)² + 2.2804P] where P = (F_o² + 2F_c²)/3
5395 reflections	(Δ/σ)_max = 0.013
324 parameters	Δρ_max = 1.14 e Å⁻³
1 restraint	Δρ_min = −0.62 e Å⁻³
Primary atom site location: structure-invariant direct methods

Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1b	0.8929 (5)	0.3755 (3)	0.63846 (13)	0.02015 (14)	0.5071 (10)
Br2a	0.7235 (3)	1.08330 (19)	1.08656 (7)	0.02015 (14)	0.4929 (10)
Mn1	1.16958 (5)	0.27016 (4)	0.67869 (2)	0.01900 (10)
Cl1e	0.9096 (19)	0.3654 (13)	0.6366 (7)	0.02015 (14)	0.282 (6)
Cl2b	0.6988 (8)	1.0673 (5)	1.08955 (18)	0.02015 (14)	0.5071 (10)
Cl3d	1.4134 (8)	0.1740 (6)	0.7245 (3)	0.02015 (14)	0.225 (6)
O1c	1.4948 (5)	0.1658 (3)	0.73470 (17)	0.0267 (7)	0.775 (6)
O2	1.3608 (3)	0.4822 (3)	0.57446 (14)	0.0396 (6)
O3	1.0876 (3)	0.5106 (2)	0.79685 (11)	0.0256 (4)
O4	0.8059 (3)	0.6321 (3)	1.04873 (13)	0.0320 (5)
O5	0.5308 (4)	0.8025 (4)	0.73664 (16)	0.0522 (7)
O30d	0.8464 (19)	0.4043 (14)	0.6329 (7)	0.0256 (4)	0.225 (6)
N1	1.2160 (3)	0.1257 (3)	0.58401 (13)	0.0188 (4)
N2	1.0398 (3)	0.1015 (2)	0.74008 (13)	0.0177 (4)
N3	0.8143 (3)	0.3242 (3)	0.88439 (13)	0.0184 (4)
N4	0.5950 (3)	0.7904 (3)	1.00838 (14)	0.0259 (5)
C1c	1.3725 (8)	0.2021 (5)	0.7131 (3)	0.0178 (10)	0.775 (6)
C2	1.2855 (4)	0.3997 (3)	0.61360 (16)	0.0253 (6)
C3	1.1152 (4)	0.4113 (3)	0.75533 (16)	0.0256 (4)
C4	1.3042 (4)	0.1405 (3)	0.50646 (16)	0.0228 (5)
C5	1.3240 (4)	0.0364 (3)	0.44579 (16)	0.0244 (6)
C6	1.2507 (4)	−0.0874 (3)	0.46607 (16)	0.0232 (6)
C7	1.1544 (4)	−0.1062 (3)	0.54725 (16)	0.0206 (5)
C8	1.1403 (3)	0.0044 (3)	0.60407 (15)	0.0178 (5)
C9	1.0684 (4)	−0.2294 (3)	0.57349 (17)	0.0243 (6)
C10	0.9738 (4)	−0.2399 (3)	0.65167 (17)	0.0237 (6)
C11	0.9597 (4)	−0.1300 (3)	0.71097 (16)	0.0205 (5)
C12	1.0435 (4)	−0.0076 (3)	0.68730 (15)	0.0182 (5)
C13	0.8665 (4)	−0.1387 (3)	0.79310 (17)	0.0248 (6)
C14	0.8659 (4)	−0.0318 (3)	0.84659 (16)	0.0238 (6)
C15	0.9550 (4)	0.0861 (3)	0.81856 (15)	0.0192 (5)
C16	0.9553 (4)	0.1955 (3)	0.88158 (15)	0.0196 (5)
C17	0.6990 (4)	0.3362 (3)	0.83615 (15)	0.0219 (5)
C18	0.5748 (4)	0.4589 (3)	0.83982 (16)	0.0246 (6)
C19	0.5704 (4)	0.5694 (3)	0.89289 (16)	0.0218 (5)
C20	0.6896 (4)	0.5542 (3)	0.94311 (15)	0.0195 (5)
C21	0.8099 (4)	0.4289 (3)	0.93797 (15)	0.0195 (5)
C22	0.7012 (4)	0.6639 (3)	1.00468 (16)	0.0221 (5)
C23	0.4337 (5)	0.7208 (4)	0.7017 (3)	0.0389 (8)
C30d	0.954 (3)	0.358 (3)	0.6374 (13)	0.0256 (4)	0.225 (6)
H1	0.5976	0.8564	1.0438	0.0310*
H2	0.5222	0.8078	0.9754	0.0310*
H3	1.3560	0.2255	0.4916	0.0273*
H4	1.3876	0.0514	0.3911	0.0293*
H5	1.2647	−0.1596	0.4258	0.0278*
H6	1.0779	−0.3045	0.5355	0.0292*
H7	0.9159	−0.3216	0.6675	0.0284*
H8	0.8048	−0.2176	0.8113	0.0298*
H9	0.8053	−0.0370	0.9027	0.0286*
H10	1.0706	0.2292	0.8689	0.0235*
H11	0.9393	0.1484	0.9366	0.0235*
H12	0.7026	0.2604	0.7995	0.0263*
H13	0.4927	0.4672	0.8060	0.0295*
H14	0.4869	0.6548	0.8951	0.0262*
H15	0.8905	0.4165	0.9727	0.0234*
H16	0.3446	0.6846	0.7454	0.0467*
H17	0.5120	0.6390	0.6718	0.0467*
H18	0.3766	0.7818	0.6633	0.0467*
H19	0.4638	0.8519	0.7755	0.1825*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1b	0.0210 (7)	0.0174 (4)	0.02220 (16)	−0.00054 (14)	−0.0062 (2)	−0.00383 (13)
Br2a	0.0210 (7)	0.0174 (4)	0.02220 (16)	−0.00054 (14)	−0.0062 (2)	−0.00383 (13)
Mn1	0.02252 (19)	0.01739 (18)	0.01732 (18)	−0.00680 (14)	−0.00191 (14)	−0.00348 (14)
Cl1e	0.0210 (7)	0.0174 (4)	0.02220 (16)	−0.00054 (14)	−0.0062 (2)	−0.00383 (13)
Cl2b	0.0210 (7)	0.0174 (4)	0.02220 (16)	−0.00054 (14)	−0.0062 (2)	−0.00383 (13)
Cl3d	0.0210 (7)	0.0174 (4)	0.02220 (16)	−0.00054 (14)	−0.0062 (2)	−0.00383 (13)
O1c	0.0226 (18)	0.0307 (15)	0.0298 (15)	−0.0056 (11)	−0.0096 (13)	−0.0077 (11)
O2	0.0465 (14)	0.0328 (12)	0.0350 (12)	−0.0179 (10)	0.0081 (10)	−0.0012 (9)
O3	0.0338 (9)	0.0217 (7)	0.0209 (7)	−0.0097 (6)	−0.0015 (7)	−0.0035 (6)
O4	0.0281 (11)	0.0317 (11)	0.0388 (12)	0.0044 (9)	−0.0161 (9)	−0.0150 (9)
O5	0.0521 (16)	0.0661 (18)	0.0409 (14)	−0.0272 (14)	−0.0018 (12)	−0.0081 (13)
O30d	0.0338 (9)	0.0217 (7)	0.0209 (7)	−0.0097 (6)	−0.0015 (7)	−0.0035 (6)
N1	0.0193 (10)	0.0184 (10)	0.0182 (10)	−0.0010 (8)	−0.0043 (8)	−0.0031 (8)
N2	0.0189 (10)	0.0166 (10)	0.0181 (10)	−0.0026 (8)	−0.0053 (8)	−0.0023 (8)
N3	0.0182 (10)	0.0193 (10)	0.0172 (10)	−0.0040 (8)	−0.0025 (8)	0.0000 (8)
N4	0.0285 (12)	0.0218 (11)	0.0280 (12)	−0.0009 (9)	−0.0089 (10)	−0.0062 (9)
C1c	0.027 (3)	0.0108 (18)	0.0118 (17)	−0.0012 (16)	0.0020 (16)	−0.0024 (13)
C2	0.0287 (14)	0.0241 (13)	0.0219 (13)	−0.0064 (11)	−0.0006 (11)	−0.0058 (10)
C3	0.0338 (9)	0.0217 (7)	0.0209 (7)	−0.0097 (6)	−0.0015 (7)	−0.0035 (6)
C4	0.0229 (13)	0.0237 (13)	0.0206 (12)	−0.0032 (10)	−0.0028 (10)	−0.0021 (10)
C5	0.0226 (13)	0.0300 (14)	0.0190 (12)	0.0002 (11)	−0.0033 (10)	−0.0040 (10)
C6	0.0240 (13)	0.0258 (13)	0.0202 (12)	0.0028 (10)	−0.0089 (10)	−0.0073 (10)
C7	0.0228 (13)	0.0188 (12)	0.0218 (12)	0.0012 (10)	−0.0101 (10)	−0.0043 (10)
C8	0.0176 (11)	0.0162 (11)	0.0198 (12)	0.0004 (9)	−0.0064 (9)	−0.0028 (9)
C9	0.0306 (14)	0.0180 (12)	0.0274 (14)	−0.0009 (10)	−0.0132 (11)	−0.0069 (10)
C10	0.0306 (14)	0.0168 (12)	0.0274 (14)	−0.0058 (10)	−0.0121 (11)	−0.0028 (10)
C11	0.0253 (13)	0.0157 (11)	0.0229 (13)	−0.0041 (10)	−0.0096 (10)	−0.0011 (10)
C12	0.0198 (12)	0.0157 (11)	0.0206 (12)	−0.0015 (9)	−0.0079 (10)	−0.0025 (9)
C13	0.0303 (14)	0.0201 (12)	0.0259 (14)	−0.0095 (11)	−0.0069 (11)	0.0022 (10)
C14	0.0276 (14)	0.0241 (13)	0.0208 (13)	−0.0079 (11)	−0.0048 (11)	0.0004 (10)
C15	0.0216 (12)	0.0181 (11)	0.0185 (12)	−0.0020 (9)	−0.0061 (10)	−0.0010 (9)
C16	0.0218 (12)	0.0187 (12)	0.0183 (12)	−0.0013 (10)	−0.0055 (10)	−0.0013 (9)
C17	0.0268 (13)	0.0226 (12)	0.0181 (12)	−0.0049 (10)	−0.0076 (10)	−0.0015 (10)
C18	0.0274 (14)	0.0260 (13)	0.0222 (13)	−0.0022 (11)	−0.0108 (11)	−0.0003 (10)
C19	0.0226 (13)	0.0208 (12)	0.0209 (12)	−0.0024 (10)	−0.0035 (10)	0.0012 (10)
C20	0.0185 (12)	0.0210 (12)	0.0179 (12)	−0.0040 (9)	−0.0012 (9)	−0.0018 (9)
C21	0.0183 (12)	0.0227 (12)	0.0173 (11)	−0.0039 (10)	−0.0024 (9)	−0.0036 (9)
C22	0.0190 (12)	0.0230 (13)	0.0235 (13)	−0.0032 (10)	−0.0019 (10)	−0.0052 (10)
C23	0.0406 (18)	0.0377 (17)	0.0436 (19)	−0.0116 (14)	−0.0181 (15)	0.0081 (14)
C30d	0.0338 (9)	0.0217 (7)	0.0209 (7)	−0.0097 (6)	−0.0015 (7)	−0.0035 (6)

Geometric parameters (Å, º) top

Br1b—Mn1	2.489 (4)	C10—C11	1.433 (4)
Mn1—Cl1e	2.365 (15)	C11—C12	1.411 (4)
Mn1—Cl3d	2.285 (7)	C11—C13	1.402 (4)
Mn1—N1	2.054 (3)	C13—C14	1.370 (4)
Mn1—N2	2.117 (2)	C14—C15	1.408 (4)
Mn1—C1c	1.846 (7)	C15—C16	1.501 (4)
Mn1—C2	1.807 (3)	C17—C18	1.384 (4)
Mn1—C3	1.811 (3)	C18—C19	1.383 (4)
Mn1—C30d	2.03 (3)	C19—C20	1.392 (4)
Cl3d—O1c	0.699 (8)	C20—C21	1.382 (4)
O1c—C1c	1.113 (8)	C20—C22	1.513 (4)
O2—C2	1.140 (4)	O5—H19	0.840
O3—C3	1.146 (4)	N4—H1	0.880
O4—C22	1.228 (4)	N4—H2	0.880
O5—C23	1.399 (6)	C4—H3	0.950
O30d—C30d	0.91 (3)	C5—H4	0.950
N1—C4	1.332 (4)	C6—H5	0.950
N1—C8	1.360 (4)	C9—H6	0.950
N2—C12	1.370 (4)	C10—H7	0.950
N2—C15	1.338 (3)	C13—H8	0.950
N3—C16	1.503 (3)	C14—H9	0.950
N3—C17	1.343 (4)	C16—H10	0.990
N3—C21	1.346 (4)	C16—H11	0.990
N4—C22	1.335 (4)	C17—H12	0.950
C4—C5	1.401 (4)	C18—H13	0.950
C5—C6	1.372 (4)	C19—H14	0.950
C6—C7	1.409 (4)	C21—H15	0.950
C7—C8	1.409 (4)	C23—H16	0.980
C7—C9	1.433 (4)	C23—H17	0.980
C8—C12	1.430 (4)	C23—H18	0.980
C9—C10	1.352 (4)

Br1b···C17	3.328 (4)	O1c···H4^iv	2.8763
Mn1···C16	3.508 (3)	O1c···H5^iv	2.8998
Cl1e···C8	3.578 (12)	O1c···H12^v	2.4627
Cl1e···C17	3.378 (11)	O1c···H13^v	3.1062
O1c···C2	3.412 (5)	O1c···H19ⁱⁱⁱ	3.0213
O1c···C3	3.447 (5)	O2···H6^vii	2.9319
O2···C1c	3.420 (5)	O2···H16^v	3.4596
O2···C3	3.290 (4)	O2···H17^v	2.8145
O2···C4	3.570 (4)	O2···H18^v	3.2633
O2···C30d	3.52 (3)	O3···H7^vii	3.0598
O3···N3	3.063 (3)	O3···H8^vii	3.0929
O3···C1c	3.496 (5)	O3···H13^v	3.2199
O3···C2	3.227 (3)	O3···H16^v	2.7709
O3···C16	3.422 (4)	O4···H10ⁱⁱ	2.3939
O3···C20	3.492 (3)	O4···H11ⁱⁱ	3.1595
O3···C21	2.990 (3)	O4···H13^viii	3.1904
O3···C30d	3.52 (3)	O4···H15ⁱⁱ	2.3286
O4···C21	2.702 (4)	O5···H4^x	2.4901
O30d···N1	3.568 (13)	O5···H7^vii	3.0641
O30d···C2	3.423 (16)	O5···H8^vii	2.7287
O30d···C3	3.292 (16)	O5···H13	3.3285
O30d···C17	3.384 (12)	O5···H14	2.8980
N1···C6	2.801 (4)	O30d···H5^xi	2.8691
N2···N3	3.256 (3)	O30d···H6^xi	2.8960
N2···C13	2.823 (4)	O30d···H7^vii	2.8209
N2···C17	3.336 (3)	O30d···H17	3.1266
N3···C3	3.012 (4)	N1···H4^iv	3.4254
N3···C14	3.361 (4)	N1···H6^xi	3.5858
N3···C19	2.744 (4)	N1···H18ⁱⁱⁱ	3.5819
N4···C19	2.948 (4)	N3···H2^viii	3.4669
C2···C4	3.042 (4)	N4···H1ⁱ	3.5748
C3···C15	3.509 (4)	N4···H8^vii	3.3172
C3···C16	3.051 (4)	N4···H9^vii	2.7806
C3···C17	3.439 (4)	N4···H12^viii	3.5726
C3···C21	3.414 (4)	C1c···H4^iv	3.1097
C4···C7	2.750 (4)	C1c···H5^iv	3.2305
C4···C12	3.595 (4)	C1c···H12^v	3.3991
C4···C30d	3.525 (18)	C1c···H13^v	3.3559
C5···C8	2.730 (4)	C1c···H19ⁱⁱⁱ	3.4121
C7···C11	2.825 (4)	C2···H6^vii	3.3623
C8···C10	2.814 (4)	C2···H7^vii	3.5759
C8···C30d	3.421 (19)	C2···H17^v	3.3903
C9···C12	2.828 (4)	C3···H7^vii	3.2235
C11···C15	2.754 (4)	C3···H13^v	3.4225
C12···C14	2.719 (4)	C3···H16^v	3.3464
C12···C30d	3.49 (2)	C4···H4^iv	3.5245
C14···C17	3.500 (4)	C4···H6^xi	3.3882
C15···C17	2.824 (4)	C4···H18^x	3.4677
C17···C20	2.751 (4)	C5···H3^iv	3.5488
C17···C30d	3.475 (19)	C5···H18^x	3.2944
C18···C21	2.733 (5)	C6···H3^iv	3.4069
Br2a···O5ⁱ	3.276 (3)	C7···H18ⁱⁱⁱ	2.9645
Br2a···N4	3.478 (4)	C8···H5^xi	3.4524
Br2a···N4ⁱ	3.326 (4)	C8···H18ⁱⁱⁱ	2.8771
Br2a···C15ⁱⁱ	3.452 (4)	C9···H18ⁱⁱⁱ	3.1731
Br2a···C16ⁱⁱ	3.464 (3)	C10···H4^xi	3.3326
Cl2b···O5ⁱ	3.218 (4)	C10···H18ⁱⁱⁱ	3.2910
Cl2b···N4	3.279 (6)	C11···H4^xi	3.5345
Cl2b···N4ⁱ	3.238 (6)	C11···H16ⁱⁱⁱ	3.4264
Cl2b···C15ⁱⁱ	3.535 (6)	C11···H18ⁱⁱⁱ	3.2024
Cl2b···C16ⁱⁱ	3.493 (6)	C12···H5^xi	3.5607
Cl3d···O5ⁱⁱⁱ	3.463 (6)	C12···H18ⁱⁱⁱ	2.9951
Cl3d···C5^iv	3.567 (6)	C13···H19^xii	3.2971
O1c···O5ⁱⁱⁱ	3.366 (4)	C14···H2^xii	3.5494
O1c···C5^iv	3.513 (4)	C17···H1^viii	3.4103
O1c···C6^iv	3.525 (4)	C17···H2^viii	3.5459
O1c···C17^v	3.223 (5)	C18···H16	3.1787
O1c···C18^v	3.537 (5)	C18···H17	3.3003
O2···O2^vi	2.961 (3)	C19···H8^vii	3.0075
O2···C9^vii	3.271 (4)	C19···H16	3.4117
O2···C23^v	3.353 (5)	C19···H19	3.3354
O3···O4ⁱⁱ	3.079 (3)	C20···H8^vii	3.0797
O3···C10^vii	3.459 (4)	C20···H14^viii	3.4206
O3···C13^vii	3.473 (3)	C21···H14^viii	3.3546
O4···O3ⁱⁱ	3.079 (3)	C21···H15ⁱⁱ	3.5967
O4···N3ⁱⁱ	3.540 (4)	C22···H8^vii	3.3205
O4···C3ⁱⁱ	3.463 (4)	C22···H9^vii	3.3249
O4···C16ⁱⁱ	3.120 (4)	C22···H10ⁱⁱ	3.3594
O4···C18^viii	3.374 (4)	C22···H13^viii	3.4392
O4···C21ⁱⁱ	3.075 (4)	C22···H15ⁱⁱ	3.3182
O5···Br2aⁱ	3.276 (3)	C23···H3^x	3.3217
O5···Cl2bⁱ	3.218 (4)	C23···H4^x	2.9310
O5···Cl3d^ix	3.463 (6)	C23···H13	2.9204
O5···O1c^ix	3.366 (4)	C23···H14	3.3662
O5···C5^x	3.370 (4)	C30d···H5^xi	3.1093
O5···C10^vii	3.441 (4)	C30d···H6^xi	3.0245
O5···C11^vii	3.491 (4)	C30d···H7^vii	3.0143
O5···C13^vii	3.162 (5)	H1···Br2a	2.6768
O5···C18	3.583 (4)	H1···Cl2b	2.4605
O5···C19	3.360 (4)	H1···Cl2bⁱ	3.5747
N3···O4ⁱⁱ	3.540 (4)	H1···O1cⁱⁱ	3.5958
N4···Br2a	3.478 (4)	H1···N4ⁱ	3.5748
N4···Br2aⁱ	3.326 (4)	H1···C17^viii	3.4103
N4···Cl2b	3.279 (6)	H1···H1ⁱ	3.3390
N4···Cl2bⁱ	3.238 (6)	H1···H2ⁱ	3.1598
N4···C14^vii	3.564 (4)	H1···H9^vii	2.7846
N4···C17^viii	3.370 (4)	H1···H9^viii	3.3154
N4···C18^viii	3.541 (4)	H1···H10ⁱⁱ	3.2747
C3···O4ⁱⁱ	3.463 (4)	H1···H12^viii	3.3723
C4···C5^iv	3.396 (4)	H2···Br2aⁱ	2.4764
C4···C9^xi	3.493 (5)	H2···Cl2bⁱ	2.3966
C5···Cl3d^iv	3.567 (6)	H2···N3^viii	3.4669
C5···O1c^iv	3.513 (4)	H2···C14^vii	3.5494
C5···O5^x	3.370 (4)	H2···C17^viii	3.5459
C5···C4^iv	3.396 (4)	H2···H1ⁱ	3.1598
C5···C9^xi	3.423 (4)	H2···H8^vii	3.0982
C5···C10^xi	3.458 (4)	H2···H9^vii	2.8713
C6···O1c^iv	3.525 (4)	H2···H9^viii	3.4147
C6···C7^xi	3.484 (4)	H2···H11^viii	3.5835
C6···C8^xi	3.533 (4)	H2···H19	3.4677
C7···C6^xi	3.484 (4)	H3···C5^iv	3.5488
C7···C7^xi	3.525 (4)	H3···C6^iv	3.4069
C8···C6^xi	3.533 (4)	H3···C23^x	3.3217
C9···O2^xii	3.271 (4)	H3···H5^iv	3.5554
C9···C4^xi	3.493 (5)	H3···H6^xi	3.5399
C9···C5^xi	3.423 (4)	H3···H17^x	2.9846
C10···O3^xii	3.459 (4)	H3···H18^x	2.9324
C10···O5^xii	3.441 (4)	H4···Cl3d^iv	2.9236
C10···C5^xi	3.458 (4)	H4···O1c^iv	2.8763
C11···O5^xii	3.491 (4)	H4···O5^x	2.4901
C13···O3^xii	3.473 (3)	H4···N1^iv	3.4254
C13···O5^xii	3.162 (5)	H4···C1c^iv	3.1097
C14···N4^xii	3.564 (4)	H4···C4^iv	3.5245
C15···Br2aⁱⁱ	3.452 (4)	H4···C10^xi	3.3326
C15···Cl2bⁱⁱ	3.535 (6)	H4···C11^xi	3.5345
C16···Br2aⁱⁱ	3.464 (3)	H4···C23^x	2.9310
C16···Cl2bⁱⁱ	3.493 (6)	H4···H7^xi	3.4793
C16···O4ⁱⁱ	3.120 (4)	H4···H17^x	3.1945
C17···O1c^xiii	3.223 (5)	H4···H18^x	2.6041
C17···N4^viii	3.370 (4)	H4···H19^x	2.9179
C18···O1c^xiii	3.537 (5)	H5···Br1b^xi	2.9032
C18···O4^viii	3.374 (4)	H5···Cl1e^xi	2.9010
C18···O5	3.583 (4)	H5···Cl3d^iv	3.1256
C18···N4^viii	3.541 (4)	H5···O1c^iv	2.8998
C18···C22^viii	3.276 (4)	H5···O30d^xi	2.8691
C18···C23	3.520 (5)	H5···C1c^iv	3.2305
C19···O5	3.360 (4)	H5···C8^xi	3.4524
C19···C20^viii	3.305 (4)	H5···C12^xi	3.5607
C19···C22^viii	3.433 (4)	H5···C30d^xi	3.1093
C20···C19^viii	3.305 (4)	H5···H3^iv	3.5554
C20···C20^viii	3.441 (4)	H6···Br1b^xi	2.9532
C21···O4ⁱⁱ	3.075 (4)	H6···Cl1e^xi	2.9268
C22···C18^viii	3.276 (4)	H6···O2^xii	2.9319
C22···C19^viii	3.433 (4)	H6···O30d^xi	2.8960
C23···O2^xiii	3.353 (5)	H6···N1^xi	3.5858
C23···C18	3.520 (5)	H6···C2^xii	3.3623
Br1b···H12	3.0025	H6···C4^xi	3.3882
Mn1···H3	3.1408	H6···C30d^xi	3.0245
Mn1···H10	3.1062	H6···H3^xi	3.5399
Cl1e···H12	3.0389	H7···Br1b^xii	2.9393
Cl3d···H10	3.1769	H7···Cl1e^xii	3.0081
O1c···H10	3.5624	H7···O3^xii	3.0598
O2···H3	2.8354	H7···O5^xii	3.0641
O3···H10	2.8542	H7···O30d^xii	2.8209
O3···H15	3.1437	H7···C2^xii	3.5759
O4···H1	2.4684	H7···C3^xii	3.2235
O4···H2	3.0347	H7···C30d^xii	3.0143
O4···H15	2.3527	H7···H4^xi	3.4793
O30d···H12	3.0829	H7···H17^xii	3.2739
O30d···H13	3.5235	H8···O3^xii	3.0929
N1···H4	3.2469	H8···O5^xii	2.7287
N2···H9	3.2548	H8···N4^xii	3.3172
N2···H10	2.5845	H8···C19^xii	3.0075
N2···H11	3.2203	H8···C20^xii	3.0797
N2···H12	2.8282	H8···C22^xii	3.3205
N3···H9	3.3914	H8···H2^xii	3.0982
N3···H13	3.2172	H8···H14^xii	2.9863
N4···H14	2.6912	H8···H19^xii	2.8784
C1c···H10	3.0870	H9···Br2a^xii	3.2000
C2···H3	2.5668	H9···Cl2b^xii	3.1874
C3···H10	2.4909	H9···N4^xii	2.7806
C4···H5	3.2584	H9···C22^xii	3.3249
C6···H3	3.2427	H9···H1^xii	2.7846
C6···H6	2.6997	H9···H1^viii	3.3154
C7···H4	3.2643	H9···H2^xii	2.8713
C7···H7	3.2789	H9···H2^viii	3.4147
C8···H3	3.1640	H10···Br2aⁱⁱ	3.2602
C8···H5	3.2753	H10···Cl2bⁱⁱ	3.2155
C8···H6	3.3067	H10···O4ⁱⁱ	2.3939
C9···H5	2.7033	H10···C22ⁱⁱ	3.3594
C10···H8	2.6885	H10···H1ⁱⁱ	3.2747
C11···H6	3.2820	H11···Br2a^xii	2.7844
C11···H9	3.2502	H11···Br2aⁱⁱ	3.1272
C12···H7	3.3110	H11···Cl2b^xii	2.9562
C12···H8	3.2745	H11···Cl2bⁱⁱ	3.1918
C13···H7	2.6820	H11···O4ⁱⁱ	3.1595
C14···H10	3.2221	H11···H2^viii	3.5835
C14···H11	2.5282	H11···H11^xiv	3.5606
C14···H12	2.9878	H12···Cl3d^xiii	3.0874
C15···H8	3.2700	H12···O1c^xiii	2.4627
C15···H12	2.4487	H12···N4^viii	3.5726
C16···H9	2.6158	H12···C1c^xiii	3.3991
C16···H12	2.6637	H12···H1^viii	3.3723
C16···H15	2.5356	H13···Cl3d^xiii	3.3265
C17···H10	3.1293	H13···O1c^xiii	3.1062
C17···H11	3.1153	H13···O3^xiii	3.2199
C17···H14	3.2541	H13···O4^viii	3.1904
C17···H15	3.1945	H13···O5	3.3285
C19···H2	2.6032	H13···C1c^xiii	3.3559
C19···H12	3.2517	H13···C3^xiii	3.4225
C19···H15	3.2470	H13···C22^viii	3.4392
C20···H1	3.2488	H13···C23	2.9204
C20···H2	2.5439	H13···H16	2.4806
C20···H13	3.2541	H13···H17	2.6833
C21···H10	2.6383	H13···H19	3.5907
C21···H11	2.6614	H14···Br2aⁱ	2.7246
C21···H12	3.1977	H14···Cl2bⁱ	2.7695
C21···H14	3.2504	H14···O5	2.8980
C22···H14	2.7865	H14···C20^viii	3.4206
C22···H15	2.5574	H14···C21^viii	3.3546
C30d···H12	3.1595	H14···C23	3.3662
H1···H14	3.5302	H14···H8^vii	2.9863
H2···H14	2.0979	H14···H15^viii	3.4238
H3···H4	2.3341	H14···H16	2.9568
H4···H5	2.3311	H14···H19	2.6711
H5···H6	2.5565	H15···O4ⁱⁱ	2.3286
H6···H7	2.2889	H15···C21ⁱⁱ	3.5967
H7···H8	2.5350	H15···C22ⁱⁱ	3.3182
H8···H9	2.3269	H15···H14^viii	3.4238
H9···H10	3.4588	H15···H15ⁱⁱ	2.8357
H9···H11	2.3297	H16···Br2aⁱ	3.5121
H9···H12	3.2974	H16···O2^xiii	3.4596
H10···H12	3.3559	H16···O3^xiii	2.7709
H10···H15	2.5364	H16···C3^xiii	3.3464
H11···H12	3.3215	H16···C11^ix	3.4264
H11···H15	2.5539	H16···C18	3.1787
H12···H13	2.3344	H16···C19	3.4117
H13···H14	2.3391	H16···H13	2.4806
H16···H19	2.0894	H16···H14	2.9568
H17···H19	2.6208	H17···Br1b	3.5386
H18···H19	2.2963	H17···O2^xiii	2.8145
Br1b···H5^xi	2.9032	H17···O30d	3.1266
Br1b···H6^xi	2.9532	H17···C2^xiii	3.3903
Br1b···H7^vii	2.9393	H17···C18	3.3003
Br1b···H17	3.5386	H17···H3^x	2.9846
Br2a···H1	2.6768	H17···H4^x	3.1945
Br2a···H2ⁱ	2.4764	H17···H7^vii	3.2739
Br2a···H9^vii	3.2000	H17···H13	2.6833
Br2a···H10ⁱⁱ	3.2602	H18···O2^xiii	3.2633
Br2a···H11^vii	2.7844	H18···N1^ix	3.5819
Br2a···H11ⁱⁱ	3.1272	H18···C4^x	3.4677
Br2a···H14ⁱ	2.7246	H18···C5^x	3.2944
Br2a···H16ⁱ	3.5121	H18···C7^ix	2.9645
Br2a···H19ⁱ	2.4721	H18···C8^ix	2.8771
Cl1e···H5^xi	2.9010	H18···C9^ix	3.1731
Cl1e···H6^xi	2.9268	H18···C10^ix	3.2910
Cl1e···H7^vii	3.0081	H18···C11^ix	3.2024
Cl2b···H1	2.4605	H18···C12^ix	2.9951
Cl2b···H1ⁱ	3.5747	H18···H3^x	2.9324
Cl2b···H2ⁱ	2.3966	H18···H4^x	2.6041
Cl2b···H9^vii	3.1874	H19···Br2aⁱ	2.4721
Cl2b···H10ⁱⁱ	3.2155	H19···Cl2bⁱ	2.4058
Cl2b···H11^vii	2.9562	H19···Cl3d^ix	3.0845
Cl2b···H11ⁱⁱ	3.1918	H19···O1c^ix	3.0213
Cl2b···H14ⁱ	2.7695	H19···C1c^ix	3.4121
Cl2b···H19ⁱ	2.4058	H19···C13^vii	3.2971
Cl3d···H4^iv	2.9236	H19···C19	3.3354
Cl3d···H5^iv	3.1256	H19···H2	3.4677
Cl3d···H12^v	3.0874	H19···H4^x	2.9179
Cl3d···H13^v	3.3265	H19···H8^vii	2.8784
Cl3d···H19ⁱⁱⁱ	3.0845	H19···H13	3.5907
O1c···H1ⁱⁱ	3.5958	H19···H14	2.6711

Br1b—Mn1—Cl1e	1.9 (3)	C10—C11—C12	119.6 (3)
Br1b—Mn1—Cl3d	176.22 (13)	C10—C11—C13	122.8 (3)
Br1b—Mn1—N1	88.09 (9)	C12—C11—C13	117.6 (3)
Br1b—Mn1—N2	88.39 (9)	N2—C12—C8	117.2 (3)
Br1b—Mn1—C1c	176.27 (15)	N2—C12—C11	123.7 (3)
Br1b—Mn1—C2	90.72 (11)	C8—C12—C11	119.1 (3)
Br1b—Mn1—C3	86.27 (12)	C11—C13—C14	118.9 (3)
Br1b—Mn1—C30d	4.2 (6)	C13—C14—C15	120.1 (3)
Cl1e—Mn1—Cl3d	177.5 (3)	N2—C15—C14	122.9 (3)
Cl1e—Mn1—N1	86.2 (3)	N2—C15—C16	120.0 (3)
Cl1e—Mn1—N2	88.3 (4)	C14—C15—C16	117.0 (2)
Cl1e—Mn1—C1c	178.0 (4)	N3—C16—C15	113.0 (3)
Cl1e—Mn1—C2	90.5 (3)	N3—C17—C18	120.0 (3)
Cl1e—Mn1—C3	88.1 (3)	C17—C18—C19	119.9 (3)
Cl1e—Mn1—C30d	3.3 (7)	C18—C19—C20	119.2 (3)
Cl3d—Mn1—N1	94.57 (14)	C19—C20—C21	118.8 (3)
Cl3d—Mn1—N2	89.46 (15)	C19—C20—C22	125.8 (3)
Cl3d—Mn1—C1c	3.5 (2)	C21—C20—C22	115.4 (3)
Cl3d—Mn1—C2	91.83 (16)	N3—C21—C20	120.8 (3)
Cl3d—Mn1—C3	91.20 (16)	O4—C22—N4	123.6 (3)
Cl3d—Mn1—C30d	179.1 (6)	O4—C22—C20	118.7 (3)
N1—Mn1—N2	79.58 (9)	N4—C22—C20	117.7 (3)
N1—Mn1—C1c	95.58 (15)	Mn1—C30d—O30d	165 (2)
N1—Mn1—C2	92.57 (11)	C23—O5—H19	109.468
N1—Mn1—C3	173.59 (11)	C22—N4—H1	120.002
N1—Mn1—C30d	85.7 (6)	C22—N4—H2	119.996
N2—Mn1—C1c	92.89 (16)	H1—N4—H2	120.002
N2—Mn1—C2	172.13 (11)	N1—C4—H3	118.518
N2—Mn1—C3	103.30 (10)	C5—C4—H3	118.509
N2—Mn1—C30d	91.4 (6)	C4—C5—H4	120.287
C1c—Mn1—C2	88.49 (18)	C6—C5—H4	120.290
C1c—Mn1—C3	90.03 (17)	C5—C6—H5	120.347
C1c—Mn1—C30d	175.7 (6)	C7—C6—H5	120.350
C2—Mn1—C3	84.44 (12)	C7—C9—H6	119.614
C2—Mn1—C30d	87.4 (6)	C10—C9—H6	119.610
C3—Mn1—C30d	88.4 (6)	C9—C10—H7	119.472
Mn1—Cl3d—O1c	162.1 (6)	C11—C10—H7	119.465
Cl3d—O1c—C1c	12.5 (5)	C11—C13—H8	120.538
Mn1—N1—C4	127.60 (19)	C14—C13—H8	120.552
Mn1—N1—C8	114.51 (16)	C13—C14—H9	119.946
C4—N1—C8	117.8 (3)	C15—C14—H9	119.946
Mn1—N2—C12	111.76 (15)	N3—C16—H10	108.976
Mn1—N2—C15	131.55 (18)	N3—C16—H11	108.972
C12—N2—C15	116.7 (2)	C15—C16—H10	108.971
C16—N3—C17	122.5 (3)	C15—C16—H11	108.966
C16—N3—C21	116.3 (3)	H10—C16—H11	107.774
C17—N3—C21	121.2 (2)	N3—C17—H12	119.984
Mn1—C1c—O1c	177.6 (4)	C18—C17—H12	119.985
Mn1—C2—O2	177.9 (3)	C17—C18—H13	120.074
Mn1—C3—O3	172.5 (3)	C19—C18—H13	120.073
N1—C4—C5	123.0 (3)	C18—C19—H14	120.380
C4—C5—C6	119.4 (3)	C20—C19—H14	120.381
C5—C6—C7	119.3 (3)	N3—C21—H15	119.573
C6—C7—C8	117.4 (3)	C20—C21—H15	119.578
C6—C7—C9	123.3 (3)	O5—C23—H16	109.472
C8—C7—C9	119.3 (3)	O5—C23—H17	109.465
N1—C8—C7	123.0 (3)	O5—C23—H18	109.465
N1—C8—C12	116.8 (3)	H16—C23—H17	109.478
C7—C8—C12	120.2 (3)	H16—C23—H18	109.473
C7—C9—C10	120.8 (3)	H17—C23—H18	109.474
C9—C10—C11	121.1 (3)

Br1b—Mn1—N1—C4	91.10 (18)	C17—N3—C16—C15	1.4 (3)
Br1b—Mn1—N1—C8	−86.13 (15)	C16—N3—C21—C20	177.54 (18)
Br1b—Mn1—N2—C12	84.85 (13)	C21—N3—C16—C15	−178.19 (18)
Br1b—Mn1—N2—C15	−93.67 (18)	C17—N3—C21—C20	−2.0 (4)
Cl1e—Mn1—N1—C4	90.8 (4)	C21—N3—C17—C18	1.2 (4)
Cl1e—Mn1—N1—C8	−86.4 (4)	N1—C4—C5—C6	−0.2 (4)
Cl1e—Mn1—N2—C12	83.0 (3)	C4—C5—C6—C7	1.1 (4)
Cl1e—Mn1—N2—C15	−95.5 (3)	C5—C6—C7—C8	−0.7 (4)
Cl3d—Mn1—N1—C4	−91.6 (2)	C5—C6—C7—C9	177.9 (3)
Cl3d—Mn1—N1—C8	91.19 (19)	C6—C7—C8—N1	−0.5 (4)
Cl3d—Mn1—N2—C12	−98.25 (17)	C6—C7—C8—C12	179.6 (2)
Cl3d—Mn1—N2—C15	83.2 (2)	C6—C7—C9—C10	−178.2 (3)
N1—Mn1—N2—C12	−3.51 (13)	C8—C7—C9—C10	0.3 (4)
N1—Mn1—N2—C15	177.97 (19)	C9—C7—C8—N1	−179.2 (3)
N2—Mn1—N1—C4	179.82 (19)	C9—C7—C8—C12	1.0 (4)
N2—Mn1—N1—C8	2.59 (14)	N1—C8—C12—N2	−1.9 (4)
C1c—Mn1—N1—C4	−88.3 (3)	N1—C8—C12—C11	178.8 (2)
C1c—Mn1—N1—C8	94.5 (2)	C7—C8—C12—N2	177.9 (2)
C2—Mn1—N1—C4	0.5 (2)	C7—C8—C12—C11	−1.3 (4)
C2—Mn1—N1—C8	−176.77 (16)	C7—C9—C10—C11	−1.3 (5)
C30d—Mn1—N1—C4	87.6 (6)	C9—C10—C11—C12	0.9 (4)
C30d—Mn1—N1—C8	−89.6 (6)	C9—C10—C11—C13	−178.4 (3)
C1c—Mn1—N2—C12	−98.65 (18)	C10—C11—C12—N2	−178.8 (3)
C1c—Mn1—N2—C15	82.8 (3)	C10—C11—C12—C8	0.4 (4)
C3—Mn1—N2—C12	170.64 (15)	C10—C11—C13—C14	177.2 (3)
C3—Mn1—N2—C15	−7.9 (2)	C12—C11—C13—C14	−2.1 (4)
C30d—Mn1—N2—C12	81.9 (6)	C13—C11—C12—N2	0.5 (4)
C30d—Mn1—N2—C15	−96.6 (6)	C13—C11—C12—C8	179.7 (3)
Mn1—N1—C4—C5	−178.11 (15)	C11—C13—C14—C15	1.2 (4)
Mn1—N1—C8—C7	178.88 (15)	C13—C14—C15—N2	1.4 (4)
Mn1—N1—C8—C12	−1.3 (3)	C13—C14—C15—C16	−177.3 (3)
C4—N1—C8—C7	1.4 (4)	N2—C15—C16—N3	85.2 (3)
C4—N1—C8—C12	−178.8 (2)	C14—C15—C16—N3	−96.0 (3)
C8—N1—C4—C5	−1.0 (4)	N3—C17—C18—C19	0.4 (4)
Mn1—N2—C12—C8	4.0 (3)	C17—C18—C19—C20	−1.2 (4)
Mn1—N2—C12—C11	−176.83 (16)	C18—C19—C20—C21	0.4 (4)
Mn1—N2—C15—C14	175.56 (14)	C18—C19—C20—C22	−179.5 (2)
Mn1—N2—C15—C16	−5.7 (4)	C19—C20—C21—N3	1.2 (4)
C12—N2—C15—C14	−2.9 (4)	C19—C20—C22—O4	175.4 (3)
C12—N2—C15—C16	175.8 (2)	C19—C20—C22—N4	−4.1 (4)
C15—N2—C12—C8	−177.3 (2)	C21—C20—C22—O4	−4.5 (4)
C15—N2—C12—C11	1.9 (4)	C21—C20—C22—N4	176.0 (2)
C16—N3—C17—C18	−178.30 (19)	C22—C20—C21—N3	−178.89 (19)

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x+2, −y+1, −z+2; (iii) x+1, y−1, z; (iv) −x+3, −y, −z+1; (v) x+1, y, z; (vi) −x+3, −y+1, −z+1; (vii) x, y+1, z; (viii) −x+1, −y+1, −z+2; (ix) x−1, y+1, z; (x) −x+2, −y+1, −z+1; (xi) −x+2, −y, −z+1; (xii) x, y−1, z; (xiii) x−1, y, z; (xiv) −x+2, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1···Br2a	0.88	2.68	3.478 (3)	152
N4—H1···Cl2b	0.88	2.46	3.279 (6)	155
N4—H2···Br2aⁱ	0.88	2.48	3.326 (3)	162
N4—H2···Cl2bⁱ	0.88	2.40	3.239 (6)	160
O5—H19···Br2aⁱ	0.84	2.47	3.276 (3)	161
O5—H19···Cl2bⁱ	0.84	2.41	3.218 (5)	163
C5—H4···O5^x	0.95	2.49	3.370 (4)	154
C6—H5···Br1b^xi	0.95	2.90	3.735 (4)	147
C16—H10···O4ⁱⁱ	0.99	2.39	3.120 (4)	130
C16—H11···Br2a^xii	0.99	2.78	3.678 (3)	150
C17—H12···O1c^xiii	0.95	2.46	3.224 (5)	137
C19—H14···Br2aⁱ	0.95	2.72	3.667 (3)	172
C19—H14···Cl2bⁱ	0.95	2.77	3.702 (6)	167
C21—H15···O4	0.95	2.35	2.702 (4)	101
C21—H15···O4ⁱⁱ	0.95	2.33	3.074 (4)	135

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x+2, −y+1, −z+2; (x) −x+2, −y+1, −z+1; (xi) −x+2, −y, −z+1; (xii) x, y−1, z; (xiii) x−1, y, z.

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fac-Bromido/chlorido­(0.50/0.50)[3-carbamoyl-1-(1,10-phenanthrolin-2-ylmeth­yl)pyridinium-κ2N,N′]tri­carbonyl­manganese(I) 0.49-bromide 0.51-chloride methanol monosolvate

Supporting information

Key indicators

checkCIF/PLATON results

fac-Bromido/chlorido(0.50/0.50)[3-carbamoyl-1-(1,10-phenanthrolin-2-ylmethyl)pyridinium-κ²N,N′]tricarbonylmanganese(I) 0.49-bromide 0.51-chloride methanol monosolvate