A new MnII coordination polymer with a double-chain structure

Che, G.-B.; Liu, C.-B.

doi:10.1107/S1600536806019647

A new Mn^II coordination polymer with a double-chain structure

In the title compound, poly[[(2-phenyl-1H-1,3,7,8,-tetraazacyclopenta[l]phenanthrene)manganese(II)]-μ-benzene-1,3-dicarboxylato], [Mn(C₈H₄O₄)(C₁₉H₁₂N₄)]_n, the Mn^II atom is hexacoordinated by two N atoms from the phenanthrene ligand, and four O atoms from three different benzene-1,3-dicarboxylate (m-BDC) ligands. The Mn^II atoms are bridged by the m-BDC ligands, forming a double-chain structure. Moreover, neighbouring double chains are in contact through π–π interactions, generating a two-dimensional supramolecular structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019647/ez2004sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019647/ez2004Isup2.hkl Contains datablock I

CCDC reference: 610761

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.004 Å
R factor = 0.044
wR factor = 0.118
Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.62
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.50 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H4     ...          ?

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

Computing details top

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: SHELXTL-Plus.

poly[[(2-phenyl-1H-1,3,7,8,- tetraazacyclopenta[l]phenanthrene)manganese(II)]- µ-benzene-1,3-dicarboxylato] top

Crystal data top

[Mn(C₈H₄O₄)(C₁₉H₁₂N₄)]	F(000) = 2104
M_r = 515.38	D_x = 1.570 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 18605 reflections
a = 15.390 (5) Å	θ = 3.4–27.4°
b = 15.935 (5) Å	µ = 0.65 mm⁻¹
c = 18.839 (5) Å	T = 292 K
β = 109.328 (5)°	Block, light yellow
V = 4360 (2) Å³	0.33 × 0.28 × 0.21 mm
Z = 8

Data collection top

Rigaku R-AXIS RAPID diffractometer	4944 independent reflections
Radiation source: rotor target	3595 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.3°
ω scans	h = −19→19
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −20→20
T_min = 0.804, T_max = 0.877	l = −22→23
18605 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0634P)² + 2.055P] where P = (F_o² + 2F_c²)/3
4944 reflections	(Δ/σ)_max = 0.001
325 parameters	Δρ_max = 1.02 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.7972 (2)	0.25337 (18)	0.17220 (15)	0.0444 (7)
H1	0.7753	0.3051	0.1507	0.053*
C2	0.7636 (2)	0.18117 (18)	0.13070 (16)	0.0541 (8)
H2	0.7216	0.1851	0.0822	0.065*
C3	0.7927 (2)	0.10466 (18)	0.16160 (15)	0.0458 (7)
H3	0.7703	0.0559	0.1346	0.055*
C4	0.85687 (17)	0.10006 (15)	0.23441 (13)	0.0294 (5)
C5	0.88930 (16)	0.17646 (15)	0.27188 (12)	0.0272 (5)
C6	0.95885 (16)	0.17628 (15)	0.34628 (12)	0.0273 (5)
C7	0.99598 (17)	0.10059 (16)	0.38220 (13)	0.0311 (5)
C8	1.0624 (2)	0.10503 (18)	0.45380 (15)	0.0435 (7)
H8	1.0881	0.0564	0.4795	0.052*
C9	1.0888 (2)	0.18174 (19)	0.48530 (16)	0.0541 (8)
H9	1.1335	0.1859	0.5326	0.065*
C10	1.0487 (2)	0.25419 (19)	0.44656 (15)	0.0483 (7)
H10	1.0674	0.3060	0.4691	0.058*
C11	0.96138 (16)	0.02410 (15)	0.34317 (13)	0.0291 (5)
C12	0.89421 (17)	0.02476 (15)	0.27339 (12)	0.0283 (5)
C13	0.93155 (17)	−0.10420 (16)	0.31284 (14)	0.0321 (5)
C14	0.93247 (18)	−0.19625 (16)	0.31426 (14)	0.0357 (6)
C15	0.9880 (2)	−0.23718 (19)	0.37842 (16)	0.0488 (7)
H15	1.0248	−0.2057	0.4188	0.059*
C16	0.9895 (3)	−0.3234 (2)	0.38328 (19)	0.0636 (10)
H16	1.0258	−0.3499	0.4271	0.076*
C17	0.9372 (3)	−0.3702 (2)	0.3230 (2)	0.0636 (10)
H17	0.9383	−0.4285	0.3259	0.076*
C18	0.8833 (3)	−0.3312 (2)	0.25854 (19)	0.0598 (9)
H18	0.8485	−0.3631	0.2177	0.072*
C19	0.8806 (2)	−0.24444 (19)	0.25420 (16)	0.0483 (7)
H19	0.8435	−0.2184	0.2105	0.058*
C20	0.84171 (17)	0.41410 (15)	0.41599 (12)	0.0277 (5)
C21	0.80534 (16)	0.43324 (15)	0.47878 (12)	0.0272 (5)
C22	0.85562 (16)	0.48345 (14)	0.53882 (11)	0.0255 (5)
H22	0.9107	0.5075	0.5389	0.031*
C23	0.82331 (16)	0.49782 (14)	0.59892 (12)	0.0255 (5)
C24	0.87878 (16)	0.54917 (15)	0.66563 (12)	0.0281 (5)
C25	0.74077 (18)	0.46191 (18)	0.59772 (13)	0.0369 (6)
H25	0.7193	0.4707	0.6378	0.044*
C26	0.69035 (19)	0.4133 (2)	0.53787 (15)	0.0456 (7)
H26	0.6348	0.3901	0.5375	0.055*
C27	0.72237 (18)	0.39898 (19)	0.47794 (14)	0.0390 (6)
H27	0.6881	0.3664	0.4374	0.047*
N1	0.85880 (14)	0.25225 (13)	0.24090 (11)	0.0316 (5)
N2	0.98490 (15)	0.25216 (13)	0.37894 (11)	0.0344 (5)
N3	0.87488 (14)	−0.05861 (13)	0.25358 (11)	0.0322 (5)
N4	0.98414 (14)	−0.05725 (14)	0.36733 (11)	0.0362 (5)
H4	1.0240	−0.0735	0.4089	0.043*
O1	0.78898 (13)	0.38171 (12)	0.35566 (9)	0.0388 (4)
O2	0.92413 (13)	0.42863 (13)	0.42417 (10)	0.0429 (5)
O3	0.85046 (12)	0.55292 (11)	0.72126 (9)	0.0345 (4)
O4	0.94784 (13)	0.58707 (12)	0.66173 (10)	0.0414 (5)
Mn1	0.91663 (2)	0.36874 (2)	0.314549 (17)	0.02609 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0551 (18)	0.0304 (14)	0.0341 (14)	−0.0013 (13)	−0.0036 (12)	0.0056 (11)
C2	0.071 (2)	0.0388 (17)	0.0313 (14)	−0.0081 (14)	−0.0121 (13)	0.0024 (12)
C3	0.0593 (19)	0.0327 (14)	0.0312 (14)	−0.0069 (13)	−0.0042 (12)	−0.0041 (11)
C4	0.0340 (13)	0.0271 (12)	0.0253 (12)	−0.0029 (10)	0.0075 (9)	0.0001 (9)
C5	0.0310 (12)	0.0274 (13)	0.0233 (11)	−0.0025 (10)	0.0091 (9)	0.0008 (9)
C6	0.0316 (12)	0.0278 (12)	0.0240 (11)	−0.0034 (9)	0.0112 (9)	0.0001 (9)
C7	0.0318 (13)	0.0319 (13)	0.0291 (12)	−0.0020 (10)	0.0094 (10)	0.0012 (10)
C8	0.0472 (17)	0.0338 (14)	0.0365 (14)	0.0017 (12)	−0.0035 (12)	0.0027 (11)
C9	0.060 (2)	0.0447 (18)	0.0356 (15)	−0.0034 (14)	−0.0132 (13)	−0.0025 (13)
C10	0.0586 (19)	0.0344 (15)	0.0373 (15)	−0.0074 (13)	−0.0035 (13)	−0.0064 (12)
C11	0.0308 (13)	0.0260 (12)	0.0299 (12)	−0.0012 (10)	0.0093 (10)	0.0007 (10)
C12	0.0342 (13)	0.0253 (12)	0.0261 (12)	−0.0011 (10)	0.0111 (9)	−0.0004 (9)
C13	0.0320 (13)	0.0279 (12)	0.0351 (13)	0.0001 (10)	0.0092 (10)	0.0013 (10)
C14	0.0394 (15)	0.0281 (13)	0.0385 (14)	0.0032 (10)	0.0114 (11)	0.0001 (11)
C15	0.0540 (18)	0.0369 (16)	0.0430 (16)	0.0075 (13)	−0.0010 (13)	−0.0007 (12)
C16	0.078 (2)	0.0389 (19)	0.059 (2)	0.0206 (17)	0.0018 (17)	0.0090 (15)
C17	0.084 (3)	0.0251 (15)	0.076 (2)	0.0076 (16)	0.0193 (19)	−0.0016 (15)
C18	0.076 (2)	0.0340 (17)	0.0579 (19)	−0.0021 (16)	0.0062 (16)	−0.0120 (15)
C19	0.0590 (19)	0.0361 (16)	0.0397 (15)	0.0036 (13)	0.0028 (13)	−0.0031 (12)
C20	0.0346 (13)	0.0266 (12)	0.0212 (11)	0.0010 (10)	0.0083 (9)	0.0037 (9)
C21	0.0287 (12)	0.0309 (13)	0.0202 (10)	0.0025 (9)	0.0058 (9)	0.0015 (9)
C22	0.0280 (12)	0.0263 (12)	0.0216 (11)	0.0010 (9)	0.0075 (9)	0.0008 (9)
C23	0.0276 (12)	0.0270 (12)	0.0210 (10)	0.0027 (9)	0.0070 (9)	0.0007 (9)
C24	0.0344 (13)	0.0248 (12)	0.0243 (11)	0.0026 (10)	0.0087 (9)	−0.0003 (9)
C25	0.0346 (14)	0.0524 (17)	0.0270 (12)	−0.0042 (12)	0.0147 (10)	−0.0051 (11)
C26	0.0313 (14)	0.069 (2)	0.0387 (15)	−0.0194 (14)	0.0151 (11)	−0.0142 (14)
C27	0.0336 (14)	0.0540 (17)	0.0277 (12)	−0.0105 (12)	0.0079 (10)	−0.0104 (12)
N1	0.0392 (12)	0.0257 (10)	0.0263 (10)	−0.0025 (9)	0.0059 (8)	0.0012 (8)
N2	0.0428 (12)	0.0287 (11)	0.0276 (10)	−0.0057 (9)	0.0063 (9)	−0.0017 (9)
N3	0.0390 (12)	0.0243 (11)	0.0322 (11)	0.0015 (9)	0.0102 (9)	0.0024 (8)
N4	0.0352 (12)	0.0369 (12)	0.0297 (11)	0.0010 (9)	0.0016 (9)	0.0021 (9)
O1	0.0424 (11)	0.0488 (12)	0.0224 (8)	−0.0017 (8)	0.0070 (7)	−0.0079 (8)
O2	0.0389 (11)	0.0609 (13)	0.0350 (10)	−0.0098 (9)	0.0203 (8)	−0.0152 (9)
O3	0.0456 (11)	0.0379 (10)	0.0236 (8)	−0.0053 (8)	0.0162 (7)	−0.0080 (7)
O4	0.0423 (11)	0.0491 (12)	0.0342 (10)	−0.0163 (9)	0.0144 (8)	−0.0084 (8)
Mn1	0.0351 (2)	0.02436 (19)	0.01921 (18)	−0.00246 (15)	0.00950 (13)	−0.00069 (14)

Geometric parameters (Å, º) top

C1—N1	1.328 (3)	C16—H16	0.9300
C1—C2	1.391 (4)	C17—C18	1.371 (5)
C1—H1	0.9300	C17—H17	0.9300
C2—C3	1.362 (4)	C18—C19	1.385 (4)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.402 (3)	C19—H19	0.9300
C3—H3	0.9300	C20—O2	1.248 (3)
C4—C5	1.413 (3)	C20—O1	1.267 (3)
C4—C12	1.425 (3)	C20—C21	1.498 (3)
C5—N1	1.356 (3)	C20—Mn1	2.639 (2)
C5—C6	1.455 (3)	C21—C27	1.384 (3)
C6—N2	1.356 (3)	C21—C22	1.392 (3)
C6—C7	1.408 (3)	C22—C23	1.398 (3)
C7—C8	1.399 (3)	C22—H22	0.9300
C7—C11	1.432 (3)	C23—C25	1.387 (3)
C8—C9	1.361 (4)	C23—C24	1.506 (3)
C8—H8	0.9300	C24—O4	1.245 (3)
C9—C10	1.396 (4)	C24—O3	1.263 (3)
C9—H9	0.9300	C25—C26	1.376 (4)
C10—N2	1.326 (3)	C25—H25	0.9300
C10—H10	0.9300	C26—C27	1.392 (4)
C11—C12	1.378 (3)	C26—H26	0.9300
C11—N4	1.380 (3)	C27—H27	0.9300
C12—N3	1.385 (3)	N1—Mn1	2.312 (2)
C13—N4	1.311 (3)	N2—Mn1	2.277 (2)
C13—N3	1.375 (3)	N4—H4	0.8600
C13—C14	1.467 (4)	O1—Mn1	2.347 (2)
C14—C19	1.382 (4)	O2—Mn1	2.2430 (18)
C14—C15	1.391 (4)	O3—Mn1ⁱ	2.1211 (17)
C15—C16	1.377 (4)	O4—Mn1ⁱⁱ	2.1046 (19)
C15—H15	0.9300	Mn1—O4ⁱⁱ	2.1047 (19)
C16—C17	1.375 (5)	Mn1—O3ⁱⁱⁱ	2.1211 (17)

N1—C1—C2	123.3 (3)	O2—C20—Mn1	58.01 (12)
N1—C1—H1	118.3	O1—C20—Mn1	62.77 (12)
C2—C1—H1	118.3	C21—C20—Mn1	174.13 (17)
C3—C2—C1	119.5 (2)	C27—C21—C22	119.9 (2)
C3—C2—H2	120.3	C27—C21—C20	119.7 (2)
C1—C2—H2	120.3	C22—C21—C20	120.4 (2)
C2—C3—C4	119.4 (2)	C21—C22—C23	120.1 (2)
C2—C3—H3	120.3	C21—C22—H22	120.0
C4—C3—H3	120.3	C23—C22—H22	120.0
C3—C4—C5	117.5 (2)	C25—C23—C22	119.3 (2)
C3—C4—C12	125.6 (2)	C25—C23—C24	120.1 (2)
C5—C4—C12	116.9 (2)	C22—C23—C24	120.6 (2)
N1—C5—C4	122.5 (2)	O4—C24—O3	124.2 (2)
N1—C5—C6	117.1 (2)	O4—C24—C23	118.3 (2)
C4—C5—C6	120.3 (2)	O3—C24—C23	117.5 (2)
N2—C6—C7	122.3 (2)	C26—C25—C23	120.7 (2)
N2—C6—C5	116.6 (2)	C26—C25—H25	119.6
C7—C6—C5	121.1 (2)	C23—C25—H25	119.6
C8—C7—C6	118.1 (2)	C25—C26—C27	120.1 (2)
C8—C7—C11	124.5 (2)	C25—C26—H26	119.9
C6—C7—C11	117.4 (2)	C27—C26—H26	119.9
C9—C8—C7	118.9 (3)	C21—C27—C26	119.9 (2)
C9—C8—H8	120.5	C21—C27—H27	120.0
C7—C8—H8	120.5	C26—C27—H27	120.0
C8—C9—C10	119.9 (2)	C1—N1—C5	117.7 (2)
C8—C9—H9	120.1	C1—N1—Mn1	125.67 (18)
C10—C9—H9	120.1	C5—N1—Mn1	116.56 (14)
N2—C10—C9	122.7 (3)	C10—N2—C6	118.1 (2)
N2—C10—H10	118.6	C10—N2—Mn1	123.80 (18)
C9—C10—H10	118.6	C6—N2—Mn1	118.09 (15)
C12—C11—N4	110.5 (2)	C13—N3—C12	105.4 (2)
C12—C11—C7	121.2 (2)	C13—N4—C11	104.7 (2)
N4—C11—C7	128.3 (2)	C13—N4—H4	127.6
C11—C12—N3	106.0 (2)	C11—N4—H4	127.6
C11—C12—C4	123.1 (2)	C20—O1—Mn1	88.53 (14)
N3—C12—C4	130.9 (2)	C20—O2—Mn1	93.83 (14)
N4—C13—N3	113.3 (2)	C24—O3—Mn1ⁱ	120.84 (16)
N4—C13—C14	123.8 (2)	C24—O4—Mn1ⁱⁱ	162.70 (18)
N3—C13—C14	122.9 (2)	O4ⁱⁱ—Mn1—O3ⁱⁱⁱ	98.59 (7)
C19—C14—C15	118.3 (3)	O4ⁱⁱ—Mn1—O2	85.22 (7)
C19—C14—C13	122.8 (2)	O3ⁱⁱⁱ—Mn1—O2	112.13 (8)
C15—C14—C13	119.0 (2)	O4ⁱⁱ—Mn1—N2	84.82 (8)
C16—C15—C14	121.2 (3)	O3ⁱⁱⁱ—Mn1—N2	158.76 (7)
C16—C15—H15	119.4	O2—Mn1—N2	89.00 (8)
C14—C15—H15	119.4	O4ⁱⁱ—Mn1—N1	123.62 (8)
C17—C16—C15	119.6 (3)	O3ⁱⁱⁱ—Mn1—N1	89.51 (7)
C17—C16—H16	120.2	O2—Mn1—N1	141.86 (7)
C15—C16—H16	120.2	N2—Mn1—N1	71.50 (7)
C18—C17—C16	120.2 (3)	O4ⁱⁱ—Mn1—O1	141.21 (7)
C18—C17—H17	119.9	O3ⁱⁱⁱ—Mn1—O1	89.82 (7)
C16—C17—H17	119.9	O2—Mn1—O1	56.80 (6)
C17—C18—C19	120.1 (3)	N2—Mn1—O1	100.67 (7)
C17—C18—H18	119.9	N1—Mn1—O1	94.06 (7)
C19—C18—H18	119.9	O4ⁱⁱ—Mn1—C20	113.23 (7)
C14—C19—C18	120.6 (3)	O3ⁱⁱⁱ—Mn1—C20	103.52 (7)
C14—C19—H19	119.7	O2—Mn1—C20	28.16 (7)
C18—C19—H19	119.7	N2—Mn1—C20	94.18 (7)
O2—C20—O1	120.6 (2)	N1—Mn1—C20	118.75 (8)
O2—C20—C21	119.7 (2)	O1—Mn1—C20	28.70 (7)
O1—C20—C21	119.7 (2)

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

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