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Exploring the role of azido anions led to the structure of this heteroleptic Fe complex with two azide ions and two quinolin-8-amine ligands.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016014808/pj2035sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989016014808/pj2035Isup2.hkl
Contains datablock I

CCDC reference: 1505176

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.053
  • wR factor = 0.121
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Non-Solvent Resd 1 N Ueq(max)/Ueq(min) Range 3.8 Ratio PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of N8 Check PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of N6 Check PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of N9 Check PLAT420_ALERT_2_C D-H Without Acceptor N3 -- H3B ... Please Check PLAT480_ALERT_4_C Long H...A H-Bond Reported H3B .. N5 .. 2.72 Ang. PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 3.758 Check PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 11 Report PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density 0 Note
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 4 Report PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min) 3 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 22 Note PLAT933_ALERT_2_G Number of OMIT records in Embedded RES ......... 4 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 9 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 0 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 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
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Bis(azido-κN)bis(quinolin-8-amine-κ2N,N')iron(II) top
Crystal data top
[Fe(N3)(C9H8N2)2]Dx = 1.578 Mg m3
Mr = 428.26Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 1795 reflections
a = 8.1798 (8) Åθ = 2.4–26.9°
b = 15.8675 (13) ŵ = 0.87 mm1
c = 27.775 (4) ÅT = 296 K
V = 3605.0 (6) Å3Prism, red
Z = 80.35 × 0.21 × 0.11 mm
F(000) = 1760
Data collection top
Bruker–Nonius Kappa CCD with an APEXII detector
diffractometer
4100 independent reflections
Radiation source: fine focus sealed tube2081 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.092
φ and ω scansθmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 109
Tmin = 0.606, Tmax = 0.746k = 2020
16951 measured reflectionsl = 3435
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0475P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
4100 reflectionsΔρmax = 0.32 e Å3
262 parametersΔρmin = 0.36 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.50883 (5)0.47368 (3)0.61957 (2)0.03352 (17)
N10.3287 (3)0.49268 (15)0.68146 (12)0.0413 (8)
H1A0.23160.47180.67330.050*
H1B0.36370.46490.70730.050*
N20.4757 (3)0.60857 (16)0.62329 (10)0.0327 (7)
N30.3216 (3)0.44621 (15)0.56279 (11)0.0341 (7)
H3A0.22370.46340.57280.041*
H3B0.34610.47450.53610.041*
N40.4890 (3)0.33703 (15)0.62114 (10)0.0309 (6)
N50.6707 (3)0.47625 (17)0.55749 (12)0.0482 (9)
N60.8137 (3)0.47003 (15)0.56124 (12)0.0387 (8)
N70.9542 (3)0.4642 (2)0.56381 (16)0.0735 (13)
N80.7006 (4)0.4793 (2)0.66995 (14)0.0680 (11)
N90.8201 (4)0.46219 (18)0.68843 (14)0.0522 (9)
N100.9391 (5)0.4460 (3)0.70919 (18)0.1184 (19)
C10.3122 (4)0.58115 (19)0.69286 (14)0.0337 (8)
C20.2228 (4)0.6099 (2)0.73119 (14)0.0439 (10)
H20.16800.57190.75090.053*
C30.2137 (4)0.6972 (3)0.74073 (15)0.0512 (11)
H30.15400.71620.76710.061*
C40.2909 (4)0.7538 (2)0.71204 (15)0.0458 (10)
H40.28480.81100.71910.055*
C50.3793 (4)0.7268 (2)0.67206 (14)0.0359 (9)
C60.4590 (4)0.7814 (2)0.64010 (15)0.0408 (10)
H60.45560.83920.64550.049*
C70.5399 (4)0.7512 (2)0.60195 (15)0.0444 (10)
H70.59180.78780.58070.053*
C80.5459 (4)0.6630 (2)0.59412 (14)0.0417 (9)
H80.60160.64290.56730.050*
C90.3901 (3)0.63909 (18)0.66224 (12)0.0277 (7)
C100.3161 (3)0.35638 (18)0.55234 (12)0.0276 (8)
C110.2290 (4)0.3235 (2)0.51487 (13)0.0378 (9)
H110.17050.35910.49460.045*
C120.2274 (4)0.2361 (2)0.50673 (15)0.0460 (10)
H120.16780.21450.48100.055*
C130.3114 (4)0.1829 (2)0.53578 (15)0.0437 (10)
H130.31080.12530.52940.052*
C140.3997 (4)0.21408 (19)0.57561 (14)0.0330 (8)
C150.4861 (4)0.1629 (2)0.60823 (14)0.0427 (10)
H150.48630.10470.60430.051*
C160.5685 (4)0.1980 (2)0.64518 (16)0.0493 (11)
H160.62580.16430.66680.059*
C170.5670 (4)0.2858 (2)0.65075 (15)0.0437 (10)
H170.62370.30910.67650.052*
C180.4037 (3)0.30219 (19)0.58328 (12)0.0280 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0268 (2)0.0307 (3)0.0430 (3)0.0016 (2)0.0010 (3)0.0070 (2)
N10.0433 (17)0.0335 (16)0.047 (2)0.0018 (13)0.0047 (16)0.0042 (14)
N20.0287 (14)0.0356 (15)0.0339 (18)0.0009 (11)0.0033 (15)0.0009 (14)
N30.0251 (13)0.0356 (15)0.042 (2)0.0024 (11)0.0027 (14)0.0039 (14)
N40.0314 (13)0.0311 (14)0.0302 (17)0.0058 (12)0.0011 (15)0.0012 (13)
N50.0304 (15)0.061 (2)0.054 (2)0.0014 (14)0.0045 (15)0.0090 (17)
N60.0358 (16)0.0280 (15)0.052 (2)0.0033 (13)0.0083 (15)0.0075 (14)
N70.0288 (16)0.073 (2)0.119 (4)0.0023 (15)0.007 (2)0.026 (2)
N80.0478 (19)0.094 (3)0.062 (3)0.0134 (19)0.025 (2)0.020 (2)
N90.0447 (19)0.051 (2)0.061 (3)0.0080 (16)0.0083 (19)0.0333 (18)
N100.084 (3)0.155 (4)0.116 (4)0.068 (3)0.053 (3)0.080 (3)
C10.0308 (17)0.0343 (19)0.036 (2)0.0068 (14)0.0010 (17)0.0049 (17)
C20.0412 (19)0.058 (2)0.033 (2)0.0112 (18)0.0085 (19)0.010 (2)
C30.054 (2)0.065 (3)0.034 (3)0.025 (2)0.006 (2)0.004 (2)
C40.051 (2)0.041 (2)0.045 (3)0.0187 (18)0.006 (2)0.008 (2)
C50.0359 (18)0.040 (2)0.032 (2)0.0067 (15)0.0071 (18)0.0013 (18)
C60.044 (2)0.0315 (18)0.047 (3)0.0025 (15)0.012 (2)0.0004 (19)
C70.043 (2)0.038 (2)0.052 (3)0.0060 (16)0.001 (2)0.013 (2)
C80.044 (2)0.047 (2)0.034 (2)0.0027 (16)0.0071 (18)0.0066 (19)
C90.0254 (15)0.0319 (18)0.026 (2)0.0081 (13)0.0032 (15)0.0002 (16)
C100.0241 (15)0.0314 (17)0.027 (2)0.0040 (13)0.0042 (15)0.0001 (16)
C110.0338 (18)0.051 (2)0.029 (2)0.0030 (16)0.0022 (17)0.0013 (19)
C120.043 (2)0.058 (3)0.037 (3)0.0142 (19)0.001 (2)0.014 (2)
C130.041 (2)0.038 (2)0.052 (3)0.0121 (17)0.013 (2)0.012 (2)
C140.0307 (17)0.0318 (19)0.036 (2)0.0013 (14)0.0095 (17)0.0008 (17)
C150.0441 (19)0.0313 (18)0.053 (3)0.0008 (17)0.012 (2)0.0004 (17)
C160.050 (2)0.040 (2)0.057 (3)0.0112 (17)0.000 (2)0.014 (2)
C170.0431 (19)0.046 (2)0.042 (3)0.0032 (17)0.0066 (19)0.001 (2)
C180.0236 (15)0.0353 (18)0.025 (2)0.0013 (14)0.0085 (15)0.0023 (16)
Geometric parameters (Å, º) top
Fe1—N82.104 (3)C3—H30.9300
Fe1—N22.160 (3)C4—C51.392 (5)
Fe1—N52.174 (3)C4—H40.9300
Fe1—N42.175 (2)C5—C61.401 (5)
Fe1—N32.241 (3)C5—C91.421 (4)
Fe1—N12.284 (3)C6—C71.338 (5)
N1—C11.445 (4)C6—H60.9300
N1—H1A0.8900C7—C81.416 (5)
N1—H1B0.8900C7—H70.9300
N2—C81.316 (4)C8—H80.9300
N2—C91.377 (4)C10—C111.365 (4)
N3—C101.455 (4)C10—C181.411 (4)
N3—H3A0.8900C11—C121.405 (4)
N3—H3B0.8900C11—H110.9300
N4—C171.321 (4)C12—C131.355 (5)
N4—C181.378 (4)C12—H120.9300
N5—N61.179 (3)C13—C141.411 (5)
N6—N71.155 (3)C13—H130.9300
N8—N91.136 (4)C14—C151.407 (5)
N9—N101.160 (4)C14—C181.415 (4)
C1—C21.370 (4)C15—C161.349 (5)
C1—C91.405 (4)C15—H150.9300
C2—C31.412 (5)C16—C171.401 (4)
C2—H20.9300C16—H160.9300
C3—C41.357 (5)C17—H170.9300
N8—Fe1—N291.14 (12)C3—C4—C5120.4 (3)
N8—Fe1—N594.16 (13)C3—C4—H4119.8
N2—Fe1—N595.49 (10)C5—C4—H4119.8
N8—Fe1—N494.82 (12)C4—C5—C6123.8 (3)
N2—Fe1—N4167.88 (9)C4—C5—C9119.1 (3)
N5—Fe1—N494.59 (10)C6—C5—C9117.0 (3)
N8—Fe1—N3170.31 (11)C7—C6—C5120.7 (3)
N2—Fe1—N398.09 (9)C7—C6—H6119.6
N5—Fe1—N382.06 (11)C5—C6—H6119.6
N4—Fe1—N376.67 (9)C6—C7—C8119.5 (3)
N8—Fe1—N188.56 (13)C6—C7—H7120.3
N2—Fe1—N175.65 (10)C8—C7—H7120.3
N5—Fe1—N1170.81 (10)N2—C8—C7122.6 (3)
N4—Fe1—N193.92 (9)N2—C8—H8118.7
N3—Fe1—N196.56 (10)C7—C8—H8118.7
C1—N1—Fe1110.7 (2)N2—C9—C1118.4 (3)
C1—N1—H1A109.5N2—C9—C5121.8 (3)
Fe1—N1—H1A109.5C1—C9—C5119.8 (3)
C1—N1—H1B109.5C11—C10—C18119.8 (3)
Fe1—N1—H1B109.5C11—C10—N3122.8 (3)
H1A—N1—H1B108.1C18—C10—N3117.4 (3)
C8—N2—C9118.3 (3)C10—C11—C12120.3 (3)
C8—N2—Fe1124.5 (2)C10—C11—H11119.8
C9—N2—Fe1116.8 (2)C12—C11—H11119.8
C10—N3—Fe1110.59 (18)C13—C12—C11121.0 (3)
C10—N3—H3A109.5C13—C12—H12119.5
Fe1—N3—H3A109.5C11—C12—H12119.5
C10—N3—H3B109.5C12—C13—C14120.5 (3)
Fe1—N3—H3B109.5C12—C13—H13119.7
H3A—N3—H3B108.1C14—C13—H13119.7
C17—N4—C18118.2 (3)C15—C14—C13124.0 (3)
C17—N4—Fe1126.2 (2)C15—C14—C18117.5 (3)
C18—N4—Fe1115.0 (2)C13—C14—C18118.5 (3)
N6—N5—Fe1122.2 (3)C16—C15—C14120.2 (3)
N7—N6—N5178.5 (5)C16—C15—H15119.9
N9—N8—Fe1158.7 (3)C14—C15—H15119.9
N8—N9—N10177.0 (5)C15—C16—C17119.3 (3)
C2—C1—C9119.7 (3)C15—C16—H16120.3
C2—C1—N1122.9 (3)C17—C16—H16120.3
C9—C1—N1117.4 (3)N4—C17—C16123.2 (4)
C1—C2—C3120.0 (3)N4—C17—H17118.4
C1—C2—H2120.0C16—C17—H17118.4
C3—C2—H2120.0N4—C18—C10118.5 (3)
C4—C3—C2121.0 (4)N4—C18—C14121.5 (3)
C4—C3—H3119.5C10—C18—C14119.9 (3)
C2—C3—H3119.5
Fe1—N1—C1—C2174.2 (3)Fe1—N3—C10—C11171.0 (2)
Fe1—N1—C1—C96.9 (3)Fe1—N3—C10—C189.9 (3)
C9—C1—C2—C32.1 (5)C18—C10—C11—C120.5 (5)
N1—C1—C2—C3179.0 (3)N3—C10—C11—C12179.6 (3)
C1—C2—C3—C40.9 (5)C10—C11—C12—C130.1 (5)
C2—C3—C4—C50.8 (6)C11—C12—C13—C141.4 (5)
C3—C4—C5—C6178.4 (3)C12—C13—C14—C15178.1 (3)
C3—C4—C5—C91.2 (5)C12—C13—C14—C182.5 (5)
C4—C5—C6—C7179.0 (3)C13—C14—C15—C16179.5 (3)
C9—C5—C6—C70.6 (5)C18—C14—C15—C160.1 (5)
C5—C6—C7—C80.5 (5)C14—C15—C16—C170.1 (5)
C9—N2—C8—C71.6 (5)C18—N4—C17—C160.7 (5)
Fe1—N2—C8—C7170.7 (2)Fe1—N4—C17—C16169.8 (3)
C6—C7—C8—N20.6 (5)C15—C16—C17—N40.5 (6)
C8—N2—C9—C1178.7 (3)C17—N4—C18—C10178.1 (3)
Fe1—N2—C9—C18.4 (3)Fe1—N4—C18—C1010.3 (3)
C8—N2—C9—C51.5 (4)C17—N4—C18—C140.5 (4)
Fe1—N2—C9—C5171.4 (2)Fe1—N4—C18—C14171.1 (2)
C2—C1—C9—N2178.4 (3)C11—C10—C18—N4179.3 (3)
N1—C1—C9—N20.5 (4)N3—C10—C18—N40.2 (4)
C2—C1—C9—C51.8 (5)C11—C10—C18—C140.6 (4)
N1—C1—C9—C5179.3 (3)N3—C10—C18—C14178.5 (3)
C4—C5—C9—N2180.0 (3)C15—C14—C18—N40.1 (4)
C6—C5—C9—N20.4 (4)C13—C14—C18—N4179.3 (3)
C4—C5—C9—C10.1 (5)C15—C14—C18—C10178.5 (3)
C6—C5—C9—C1179.7 (3)C13—C14—C18—C102.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N10i0.892.623.361 (6)141
N1—H1B···N10ii0.892.423.254 (6)157
N3—H3A···N7i0.892.223.019 (4)149
N3—H3B···N5iii0.892.723.561 (4)159
Symmetry codes: (i) x1, y, z; (ii) x1/2, y, z+3/2; (iii) x+1, y+1, z+1.
 

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