Download citation
Download citation
link to html
The reaction of terephthalo­nitrile and sodium azide catalyzed by manganese chloride tetrahydrate converts one nitrile group to tetrazole and leaves the other nitrile group unchanged. The MnII atom in the title compound, [Mn(H2O)6](C8H4N5)2, is coordinated by six water mol­ecules and lies on a position of 2/m crystallographic symmetry. The plane of the tetrazolate anion is perpendicular to a crystallographic mirror plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680403106X/br6174sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680403106X/br6174Isup2.hkl
Contains datablock I

CCDC reference: 262220

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.110
  • Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for Mn1
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C6 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.03 PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc. PLAT354_ALERT_3_C Short O-H Bond (0.82A) O1 - H1W2 ... 0.70 Ang. PLAT354_ALERT_3_C Short O-H Bond (0.82A) O2 - H2W1 ... 0.70 Ang. PLAT354_ALERT_3_C Short O-H Bond (0.82A) O2 - H2W2 ... 0.66 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 32.00 Deg. N1 -C6 -N1 6.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 17.00 Deg. N1 -C6 -N1' 6.555 1.555 6.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 34.00 Deg. N1 -C6 -N1' 1.555 1.555 6.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 34.00 Deg. N1 -C6 -N1' 6.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 17.00 Deg. N1 -C6 -N1' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 26.00 Deg. N1' -C6 -N1' 6.555 1.555 1.555
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C16 H20 Mn1 N10 O6 Atom count from _chemical_formula_moiety:C16 H28 Mn1 N10 O6
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker 2001); 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.

Hexaaquamanganese(II) bis[5-(4-cyanophenyl)-2H-tetrazolate] top
Crystal data top
[Mn(H2O)6](C8H4N5)2F(000) = 518
Mr = 503.36Dx = 1.489 Mg m3
Monoclinic, C2/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yCell parameters from 3037 reflections
a = 13.5565 (9) Åθ = 2.5–28.1°
b = 10.2568 (7) ŵ = 0.64 mm1
c = 8.1885 (5) ÅT = 296 K
β = 99.524 (1)°Prism, colorless
V = 1122.89 (13) Å30.40 × 0.36 × 0.20 mm
Z = 2
Data collection top
Bruker SMART APEX 2000
diffractometer
1284 independent reflections
Radiation source: fine-focus sealed tube1262 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scansθmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1716
Tmin = 0.783, Tmax = 0.882k = 1313
4708 measured reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.15 w = 1/[σ2(Fo2) + (0.0577P)2 + 0.8233P]
where P = (Fo2 + 2Fc2)/3
1284 reflections(Δ/σ)max < 0.001
112 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
xyzUiso*/UeqOcc. (<1)
Mn10.00000.00000.00000.0360 (2)
O10.11681 (14)0.14023 (18)0.0510 (3)0.0693 (6)
O20.0215 (3)0.00000.2585 (4)0.0978 (14)
C10.3190 (2)0.00000.3754 (4)0.0647 (11)
C20.3619 (2)0.1158 (3)0.3430 (4)0.0725 (8)
H2A0.33140.19410.36260.087*
C30.45063 (18)0.1158 (3)0.2811 (3)0.0593 (6)
H3A0.48000.19460.25950.071*
C40.4960 (2)0.00000.2511 (3)0.0408 (6)
C50.59140 (19)0.00000.1892 (3)0.0374 (6)
C60.2286 (3)0.00000.4451 (5)0.0854 (16)
N10.153 (3)0.031 (13)0.483 (3)0.071 (15)0.25
N1'0.165 (3)0.026 (9)0.522 (3)0.063 (13)0.25
N20.64006 (13)0.10642 (17)0.1578 (2)0.0482 (4)
N30.72188 (13)0.06365 (18)0.1035 (2)0.0497 (5)
H1W10.119 (2)0.204 (3)0.090 (3)0.054 (8)*
H1W20.158 (2)0.135 (3)0.011 (4)0.072 (10)*
H2W10.066 (5)0.00000.292 (7)0.099 (19)*
H2W20.021 (5)0.00000.311 (9)0.12 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0272 (3)0.0328 (3)0.0515 (4)0.0000.0165 (2)0.000
O10.0451 (10)0.0445 (9)0.1301 (18)0.0135 (7)0.0488 (11)0.0299 (10)
O20.0417 (16)0.199 (5)0.0578 (17)0.0000.0243 (14)0.000
C10.0304 (15)0.122 (3)0.0442 (16)0.0000.0148 (12)0.000
C20.0482 (13)0.098 (2)0.0783 (17)0.0219 (14)0.0306 (12)0.0001 (15)
C30.0470 (12)0.0621 (15)0.0756 (16)0.0086 (11)0.0298 (11)0.0020 (12)
C40.0309 (13)0.0550 (16)0.0389 (13)0.0000.0127 (10)0.000
C50.0322 (12)0.0418 (14)0.0409 (13)0.0000.0142 (10)0.000
C60.0370 (18)0.172 (5)0.0503 (19)0.0000.0167 (15)0.000
N10.035 (8)0.14 (4)0.038 (11)0.002 (13)0.012 (8)0.006 (19)
N1'0.042 (9)0.11 (4)0.038 (11)0.005 (12)0.010 (8)0.003 (19)
N20.0415 (9)0.0402 (9)0.0696 (11)0.0040 (7)0.0288 (8)0.0073 (8)
N30.0413 (9)0.0460 (9)0.0685 (11)0.0013 (8)0.0285 (8)0.0050 (8)
Geometric parameters (Å, º) top
Mn1—O1i2.1288 (17)C3—C41.379 (3)
Mn1—O12.1288 (17)C3—H3A0.9300
Mn1—O1ii2.1288 (17)C4—C3ii1.379 (3)
Mn1—O1iii2.1288 (17)C4—C51.464 (3)
Mn1—O22.184 (3)C5—N2ii1.322 (2)
Mn1—O2i2.184 (3)C5—N21.322 (2)
O1—H1W10.72 (3)C6—N1ii1.17 (5)
O1—H1W20.70 (3)C6—N11.17 (5)
O2—H2W10.71 (6)C6—N1'ii1.18 (5)
O2—H2W20.66 (7)C6—N1'1.18 (5)
C1—C21.367 (4)N1—N1ii0.6 (3)
C1—C2ii1.367 (4)N1'—N1'ii0.54 (18)
C1—C61.435 (4)N2—N31.336 (2)
C2—C31.381 (3)N3—N3ii1.306 (4)
C2—H2A0.9300
O1i—Mn1—O1180.00 (9)C1—C2—H2A120.1
O1i—Mn1—O1ii94.99 (11)C3—C2—H2A120.1
O1—Mn1—O1ii85.01 (11)C4—C3—C2120.5 (3)
O1i—Mn1—O1iii85.01 (11)C4—C3—H3A119.8
O1—Mn1—O1iii94.99 (11)C2—C3—H3A119.8
O1ii—Mn1—O1iii180.00 (9)C3ii—C4—C3119.0 (3)
O1i—Mn1—O291.38 (10)C3ii—C4—C5120.49 (14)
O1—Mn1—O288.62 (10)C3—C4—C5120.49 (14)
O1ii—Mn1—O288.62 (10)N2ii—C5—N2111.3 (2)
O1iii—Mn1—O291.38 (10)N2ii—C5—C4124.37 (11)
O1i—Mn1—O2i88.62 (10)N2—C5—C4124.37 (11)
O1—Mn1—O2i91.38 (10)N1ii—C6—N132 (10)
O1ii—Mn1—O2i91.38 (10)N1ii—C6—N1'ii17 (3)
O1iii—Mn1—O2i88.62 (10)N1—C6—N1'ii34 (2)
O2—Mn1—O2i180.00 (18)N1ii—C6—N1'34 (2)
Mn1—O1—H1W1132 (2)N1—C6—N1'17 (3)
Mn1—O1—H1W2119 (3)N1'ii—C6—N1'26 (9)
H1W1—O1—H1W2107 (3)N1ii—C6—C1163 (6)
Mn1—O2—H2W1130 (5)N1—C6—C1163 (6)
Mn1—O2—H2W2114 (6)N1'ii—C6—C1164 (4)
H2W1—O2—H2W2117 (7)N1'—C6—C1164 (4)
C2—C1—C2ii120.6 (3)N1ii—N1—C674 (6)
C2—C1—C6119.69 (15)N1'ii—N1'—C677 (4)
C2ii—C1—C6119.69 (15)C5—N2—N3105.20 (17)
C1—C2—C3119.7 (3)N3ii—N3—N2109.18 (11)
Symmetry codes: (i) x, y, z; (ii) x, y, z; (iii) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2W2···N10.66 (7)2.11 (8)2.76 (4)171 (4)
O1—H1W1···N2iv0.72 (3)2.03 (3)2.743 (3)168 (3)
O1—H1W2···N3v0.70 (3)2.14 (3)2.813 (2)164 (4)
Symmetry codes: (iv) x+1/2, y1/2, z; (v) x1, y, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds