Crystal structure of bis­(azido-κN)bis­(quinolin-8-amine-κ²N,N′)iron(II)

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.

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

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Computing details

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)

Crystal data

[Fe(N3)(C9H8N2)2]	Dx = 1.578 Mg m^−3
Mr = 428.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1795 reflections
a = 8.1798 (8) Å	θ = 2.4–26.9°
b = 15.8675 (13) Å	µ = 0.87 mm^−1
c = 27.775 (4) Å	T = 296 K
V = 3605.0 (6) Å^3	Prism, red
Z = 8	0.35 × 0.21 × 0.11 mm
F(000) = 1760

Data collection

Bruker–Nonius Kappa CCD with an APEXII detector diffractometer	4100 independent reflections
Radiation source: fine focus sealed tube	2081 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.092
φ and ω scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→9
Tmin = 0.606, Tmax = 0.746	k = −20→20
16951 measured reflections	l = −34→35

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0475P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
4100 reflections	Δρmax = 0.32 e Å^−3
262 parameters	Δρmin = −0.36 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.50883 (5)	0.47368 (3)	0.61957 (2)	0.03352 (17)
N1	0.3287 (3)	0.49268 (15)	0.68146 (12)	0.0413 (8)
H1A	0.2316	0.4718	0.6733	0.050*
H1B	0.3637	0.4649	0.7073	0.050*
N2	0.4757 (3)	0.60857 (16)	0.62329 (10)	0.0327 (7)
N3	0.3216 (3)	0.44621 (15)	0.56279 (11)	0.0341 (7)
H3A	0.2237	0.4634	0.5728	0.041*
H3B	0.3461	0.4745	0.5361	0.041*
N4	0.4890 (3)	0.33703 (15)	0.62114 (10)	0.0309 (6)
N5	0.6707 (3)	0.47625 (17)	0.55749 (12)	0.0482 (9)
N6	0.8137 (3)	0.47003 (15)	0.56124 (12)	0.0387 (8)
N7	0.9542 (3)	0.4642 (2)	0.56381 (16)	0.0735 (13)
N8	0.7006 (4)	0.4793 (2)	0.66995 (14)	0.0680 (11)
N9	0.8201 (4)	0.46219 (18)	0.68843 (14)	0.0522 (9)
N10	0.9391 (5)	0.4460 (3)	0.70919 (18)	0.1184 (19)
C1	0.3122 (4)	0.58115 (19)	0.69286 (14)	0.0337 (8)
C2	0.2228 (4)	0.6099 (2)	0.73119 (14)	0.0439 (10)
H2	0.1680	0.5719	0.7509	0.053*
C3	0.2137 (4)	0.6972 (3)	0.74073 (15)	0.0512 (11)
H3	0.1540	0.7162	0.7671	0.061*
C4	0.2909 (4)	0.7538 (2)	0.71204 (15)	0.0458 (10)
H4	0.2848	0.8110	0.7191	0.055*
C5	0.3793 (4)	0.7268 (2)	0.67206 (14)	0.0359 (9)
C6	0.4590 (4)	0.7814 (2)	0.64010 (15)	0.0408 (10)
H6	0.4556	0.8392	0.6455	0.049*
C7	0.5399 (4)	0.7512 (2)	0.60195 (15)	0.0444 (10)
H7	0.5918	0.7878	0.5807	0.053*
C8	0.5459 (4)	0.6630 (2)	0.59412 (14)	0.0417 (9)
H8	0.6016	0.6429	0.5673	0.050*
C9	0.3901 (3)	0.63909 (18)	0.66224 (12)	0.0277 (7)
C10	0.3161 (3)	0.35638 (18)	0.55234 (12)	0.0276 (8)
C11	0.2290 (4)	0.3235 (2)	0.51487 (13)	0.0378 (9)
H11	0.1705	0.3591	0.4946	0.045*
C12	0.2274 (4)	0.2361 (2)	0.50673 (15)	0.0460 (10)
H12	0.1678	0.2145	0.4810	0.055*
C13	0.3114 (4)	0.1829 (2)	0.53578 (15)	0.0437 (10)
H13	0.3108	0.1253	0.5294	0.052*
C14	0.3997 (4)	0.21408 (19)	0.57561 (14)	0.0330 (8)
C15	0.4861 (4)	0.1629 (2)	0.60823 (14)	0.0427 (10)
H15	0.4863	0.1047	0.6043	0.051*
C16	0.5685 (4)	0.1980 (2)	0.64518 (16)	0.0493 (11)
H16	0.6258	0.1643	0.6668	0.059*
C17	0.5670 (4)	0.2858 (2)	0.65075 (15)	0.0437 (10)
H17	0.6237	0.3091	0.6765	0.052*
C18	0.4037 (3)	0.30219 (19)	0.58328 (12)	0.0280 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0268 (2)	0.0307 (3)	0.0430 (3)	0.0016 (2)	−0.0010 (3)	−0.0070 (2)
N1	0.0433 (17)	0.0335 (16)	0.047 (2)	0.0018 (13)	0.0047 (16)	0.0042 (14)
N2	0.0287 (14)	0.0356 (15)	0.0339 (18)	−0.0009 (11)	0.0033 (15)	−0.0009 (14)
N3	0.0251 (13)	0.0356 (15)	0.042 (2)	0.0024 (11)	0.0027 (14)	0.0039 (14)
N4	0.0314 (13)	0.0311 (14)	0.0302 (17)	0.0058 (12)	−0.0011 (15)	−0.0012 (13)
N5	0.0304 (15)	0.061 (2)	0.054 (2)	−0.0014 (14)	0.0045 (15)	−0.0090 (17)
N6	0.0358 (16)	0.0280 (15)	0.052 (2)	−0.0033 (13)	0.0083 (15)	−0.0075 (14)
N7	0.0288 (16)	0.073 (2)	0.119 (4)	0.0023 (15)	0.007 (2)	−0.026 (2)
N8	0.0478 (19)	0.094 (3)	0.062 (3)	0.0134 (19)	−0.025 (2)	−0.020 (2)
N9	0.0447 (19)	0.051 (2)	0.061 (3)	0.0080 (16)	−0.0083 (19)	−0.0333 (18)
N10	0.084 (3)	0.155 (4)	0.116 (4)	0.068 (3)	−0.053 (3)	−0.080 (3)
C1	0.0308 (17)	0.0343 (19)	0.036 (2)	0.0068 (14)	0.0010 (17)	0.0049 (17)
C2	0.0412 (19)	0.058 (2)	0.033 (2)	0.0112 (18)	0.0085 (19)	0.010 (2)
C3	0.054 (2)	0.065 (3)	0.034 (3)	0.025 (2)	0.006 (2)	−0.004 (2)
C4	0.051 (2)	0.041 (2)	0.045 (3)	0.0187 (18)	−0.006 (2)	−0.008 (2)
C5	0.0359 (18)	0.040 (2)	0.032 (2)	0.0067 (15)	−0.0071 (18)	−0.0013 (18)
C6	0.044 (2)	0.0315 (18)	0.047 (3)	−0.0025 (15)	−0.012 (2)	0.0004 (19)
C7	0.043 (2)	0.038 (2)	0.052 (3)	−0.0060 (16)	−0.001 (2)	0.013 (2)
C8	0.044 (2)	0.047 (2)	0.034 (2)	−0.0027 (16)	0.0071 (18)	0.0066 (19)
C9	0.0254 (15)	0.0319 (18)	0.026 (2)	0.0081 (13)	−0.0032 (15)	−0.0002 (16)
C10	0.0241 (15)	0.0314 (17)	0.027 (2)	−0.0040 (13)	0.0042 (15)	−0.0001 (16)
C11	0.0338 (18)	0.051 (2)	0.029 (2)	−0.0030 (16)	−0.0022 (17)	−0.0013 (19)
C12	0.043 (2)	0.058 (3)	0.037 (3)	−0.0142 (19)	−0.001 (2)	−0.014 (2)
C13	0.041 (2)	0.038 (2)	0.052 (3)	−0.0121 (17)	0.013 (2)	−0.012 (2)
C14	0.0307 (17)	0.0318 (19)	0.036 (2)	−0.0013 (14)	0.0095 (17)	−0.0008 (17)
C15	0.0441 (19)	0.0313 (18)	0.053 (3)	−0.0008 (17)	0.012 (2)	0.0004 (17)
C16	0.050 (2)	0.040 (2)	0.057 (3)	0.0112 (17)	0.000 (2)	0.014 (2)
C17	0.0431 (19)	0.046 (2)	0.042 (3)	0.0032 (17)	−0.0066 (19)	0.001 (2)
C18	0.0236 (15)	0.0353 (18)	0.025 (2)	−0.0013 (14)	0.0085 (15)	−0.0023 (16)

Geometric parameters (Å, º)

Fe1—N8	2.104 (3)	C3—H3	0.9300
Fe1—N2	2.160 (3)	C4—C5	1.392 (5)
Fe1—N5	2.174 (3)	C4—H4	0.9300
Fe1—N4	2.175 (2)	C5—C6	1.401 (5)
Fe1—N3	2.241 (3)	C5—C9	1.421 (4)
Fe1—N1	2.284 (3)	C6—C7	1.338 (5)
N1—C1	1.445 (4)	C6—H6	0.9300
N1—H1A	0.8900	C7—C8	1.416 (5)
N1—H1B	0.8900	C7—H7	0.9300
N2—C8	1.316 (4)	C8—H8	0.9300
N2—C9	1.377 (4)	C10—C11	1.365 (4)
N3—C10	1.455 (4)	C10—C18	1.411 (4)
N3—H3A	0.8900	C11—C12	1.405 (4)
N3—H3B	0.8900	C11—H11	0.9300
N4—C17	1.321 (4)	C12—C13	1.355 (5)
N4—C18	1.378 (4)	C12—H12	0.9300
N5—N6	1.179 (3)	C13—C14	1.411 (5)
N6—N7	1.155 (3)	C13—H13	0.9300
N8—N9	1.136 (4)	C14—C15	1.407 (5)
N9—N10	1.160 (4)	C14—C18	1.415 (4)
C1—C2	1.370 (4)	C15—C16	1.349 (5)
C1—C9	1.405 (4)	C15—H15	0.9300
C2—C3	1.412 (5)	C16—C17	1.401 (4)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.357 (5)	C17—H17	0.9300
N8—Fe1—N2	91.14 (12)	C3—C4—C5	120.4 (3)
N8—Fe1—N5	94.16 (13)	C3—C4—H4	119.8
N2—Fe1—N5	95.49 (10)	C5—C4—H4	119.8
N8—Fe1—N4	94.82 (12)	C4—C5—C6	123.8 (3)
N2—Fe1—N4	167.88 (9)	C4—C5—C9	119.1 (3)
N5—Fe1—N4	94.59 (10)	C6—C5—C9	117.0 (3)
N8—Fe1—N3	170.31 (11)	C7—C6—C5	120.7 (3)
N2—Fe1—N3	98.09 (9)	C7—C6—H6	119.6
N5—Fe1—N3	82.06 (11)	C5—C6—H6	119.6
N4—Fe1—N3	76.67 (9)	C6—C7—C8	119.5 (3)
N8—Fe1—N1	88.56 (13)	C6—C7—H7	120.3
N2—Fe1—N1	75.65 (10)	C8—C7—H7	120.3
N5—Fe1—N1	170.81 (10)	N2—C8—C7	122.6 (3)
N4—Fe1—N1	93.92 (9)	N2—C8—H8	118.7
N3—Fe1—N1	96.56 (10)	C7—C8—H8	118.7
C1—N1—Fe1	110.7 (2)	N2—C9—C1	118.4 (3)
C1—N1—H1A	109.5	N2—C9—C5	121.8 (3)
Fe1—N1—H1A	109.5	C1—C9—C5	119.8 (3)
C1—N1—H1B	109.5	C11—C10—C18	119.8 (3)
Fe1—N1—H1B	109.5	C11—C10—N3	122.8 (3)
H1A—N1—H1B	108.1	C18—C10—N3	117.4 (3)
C8—N2—C9	118.3 (3)	C10—C11—C12	120.3 (3)
C8—N2—Fe1	124.5 (2)	C10—C11—H11	119.8
C9—N2—Fe1	116.8 (2)	C12—C11—H11	119.8
C10—N3—Fe1	110.59 (18)	C13—C12—C11	121.0 (3)
C10—N3—H3A	109.5	C13—C12—H12	119.5
Fe1—N3—H3A	109.5	C11—C12—H12	119.5
C10—N3—H3B	109.5	C12—C13—C14	120.5 (3)
Fe1—N3—H3B	109.5	C12—C13—H13	119.7
H3A—N3—H3B	108.1	C14—C13—H13	119.7
C17—N4—C18	118.2 (3)	C15—C14—C13	124.0 (3)
C17—N4—Fe1	126.2 (2)	C15—C14—C18	117.5 (3)
C18—N4—Fe1	115.0 (2)	C13—C14—C18	118.5 (3)
N6—N5—Fe1	122.2 (3)	C16—C15—C14	120.2 (3)
N7—N6—N5	178.5 (5)	C16—C15—H15	119.9
N9—N8—Fe1	158.7 (3)	C14—C15—H15	119.9
N8—N9—N10	177.0 (5)	C15—C16—C17	119.3 (3)
C2—C1—C9	119.7 (3)	C15—C16—H16	120.3
C2—C1—N1	122.9 (3)	C17—C16—H16	120.3
C9—C1—N1	117.4 (3)	N4—C17—C16	123.2 (4)
C1—C2—C3	120.0 (3)	N4—C17—H17	118.4
C1—C2—H2	120.0	C16—C17—H17	118.4
C3—C2—H2	120.0	N4—C18—C10	118.5 (3)
C4—C3—C2	121.0 (4)	N4—C18—C14	121.5 (3)
C4—C3—H3	119.5	C10—C18—C14	119.9 (3)
C2—C3—H3	119.5
Fe1—N1—C1—C2	−174.2 (3)	Fe1—N3—C10—C11	−171.0 (2)
Fe1—N1—C1—C9	6.9 (3)	Fe1—N3—C10—C18	9.9 (3)
C9—C1—C2—C3	−2.1 (5)	C18—C10—C11—C12	−0.5 (5)
N1—C1—C2—C3	179.0 (3)	N3—C10—C11—C12	−179.6 (3)
C1—C2—C3—C4	0.9 (5)	C10—C11—C12—C13	0.1 (5)
C2—C3—C4—C5	0.8 (6)	C11—C12—C13—C14	1.4 (5)
C3—C4—C5—C6	178.4 (3)	C12—C13—C14—C15	178.1 (3)
C3—C4—C5—C9	−1.2 (5)	C12—C13—C14—C18	−2.5 (5)
C4—C5—C6—C7	−179.0 (3)	C13—C14—C15—C16	179.5 (3)
C9—C5—C6—C7	0.6 (5)	C18—C14—C15—C16	0.1 (5)
C5—C6—C7—C8	−0.5 (5)	C14—C15—C16—C17	0.1 (5)
C9—N2—C8—C7	1.6 (5)	C18—N4—C17—C16	0.7 (5)
Fe1—N2—C8—C7	−170.7 (2)	Fe1—N4—C17—C16	−169.8 (3)
C6—C7—C8—N2	−0.6 (5)	C15—C16—C17—N4	−0.5 (6)
C8—N2—C9—C1	178.7 (3)	C17—N4—C18—C10	178.1 (3)
Fe1—N2—C9—C1	−8.4 (3)	Fe1—N4—C18—C10	−10.3 (3)
C8—N2—C9—C5	−1.5 (4)	C17—N4—C18—C14	−0.5 (4)
Fe1—N2—C9—C5	171.4 (2)	Fe1—N4—C18—C14	171.1 (2)
C2—C1—C9—N2	−178.4 (3)	C11—C10—C18—N4	−179.3 (3)
N1—C1—C9—N2	0.5 (4)	N3—C10—C18—N4	−0.2 (4)
C2—C1—C9—C5	1.8 (5)	C11—C10—C18—C14	−0.6 (4)
N1—C1—C9—C5	−179.3 (3)	N3—C10—C18—C14	178.5 (3)
C4—C5—C9—N2	−180.0 (3)	C15—C14—C18—N4	0.1 (4)
C6—C5—C9—N2	0.4 (4)	C13—C14—C18—N4	−179.3 (3)
C4—C5—C9—C1	−0.1 (5)	C15—C14—C18—C10	−178.5 (3)
C6—C5—C9—C1	−179.7 (3)	C13—C14—C18—C10	2.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N10^i	0.89	2.62	3.361 (6)	141
N1—H1B···N10^ii	0.89	2.42	3.254 (6)	157
N3—H3A···N7^i	0.89	2.22	3.019 (4)	149
N3—H3B···N5^iii	0.89	2.72	3.561 (4)	159

Symmetry codes: (i) x−1, y, z; (ii) x−1/2, y, −z+3/2; (iii) −x+1, −y+1, −z+1.