catena-Poly[[bis­(tetra­hydro­furan)lithium(I)]-μ-N-(2-isopropyl­phen­yl)benzamidinato]

The title compound, [Li(C₁₆H₁₇N₂)(C₄H₈O)₂]_n, is an unsymmetrical benzamidinate exhibiting a one-dimensional chain made up of lithium-linked N—C—N units. Two tetra­hydro­furan mol­ecules complete the distorted LiO₂N₂ tetra­hedral coordination.

Key indicators

• Single-crystal X-ray study
• T = 203 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.060
• wR factor = 0.148
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.818     0.986
            Tmin(prime) and Tmax expected:      0.978     0.986
            RR(prime) =      0.836
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.84
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.06 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2     ...          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

catena-Poly[[bis(tetrahydrofuran)lithium(I)]-µ-N-(2- isopropylphenyl)benzamidinato]

Crystal data

[Li(C16H17N2)(C4H8O)2]	F(000) = 840
Mr = 388.46	Dx = 1.150 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2066 reflections
a = 8.964 (2) Å	θ = 2.3–21.6°
b = 11.174 (3) Å	µ = 0.07 mm^−1
c = 22.689 (6) Å	T = 203 K
β = 99.142 (4)°	Prism, colourless
V = 2243.7 (10) Å^3	0.30 × 0.30 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3948 independent reflections
Radiation source: fine-focus sealed tube	3074 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.818, Tmax = 0.986	k = −13→12
9335 measured reflections	l = −26→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0504P)^2 + 1.379P] where P = (Fo^2 + 2Fc^2)/3
3948 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.77516 (19)	0.72844 (15)	0.20469 (7)	0.0264 (4)
N2	0.7387 (2)	0.53061 (16)	0.24047 (8)	0.0355 (5)
H2	0.7274	0.5047	0.2043	0.043*
C1	0.6718 (2)	0.70315 (18)	0.15187 (9)	0.0259 (5)
C2	0.7142 (2)	0.64135 (19)	0.10306 (9)	0.0279 (5)
C3	0.6069 (3)	0.6257 (2)	0.05238 (10)	0.0354 (5)
H3A	0.6340	0.5848	0.0200	0.042*
C4	0.4611 (3)	0.6688 (2)	0.04844 (11)	0.0401 (6)
H4A	0.3918	0.6575	0.0138	0.048*
C5	0.4196 (3)	0.7287 (2)	0.09625 (11)	0.0381 (6)
H5A	0.3217	0.7578	0.0942	0.046*
C6	0.5237 (2)	0.74530 (19)	0.14733 (10)	0.0318 (5)
H6A	0.4946	0.7856	0.1795	0.038*
C7	0.8752 (2)	0.5982 (2)	0.10468 (10)	0.0343 (5)
H7A	0.9237	0.5988	0.1466	0.041*
C8	0.9632 (3)	0.6834 (3)	0.07128 (15)	0.0629 (8)
H8A	0.9554	0.7632	0.0863	0.094*
H8B	0.9225	0.6815	0.0295	0.094*
H8C	1.0674	0.6597	0.0769	0.094*
C9	0.8855 (3)	0.4712 (2)	0.08182 (14)	0.0558 (8)
H9A	0.9898	0.4491	0.0840	0.084*
H9B	0.8360	0.4667	0.0411	0.084*
H9C	0.8373	0.4174	0.1059	0.084*
C10	0.7968 (2)	0.63868 (18)	0.24404 (9)	0.0258 (5)
C11	0.9030 (2)	0.66546 (19)	0.30034 (9)	0.0268 (5)
C12	0.8953 (3)	0.7724 (2)	0.33091 (9)	0.0340 (5)
H12A	0.8226	0.8289	0.3163	0.041*
C13	0.9944 (3)	0.7957 (2)	0.38273 (10)	0.0432 (6)
H13A	0.9873	0.8673	0.4030	0.052*
C14	1.1037 (3)	0.7134 (3)	0.40455 (11)	0.0468 (7)
H14A	1.1708	0.7294	0.4393	0.056*
C15	1.1127 (3)	0.6072 (2)	0.37443 (10)	0.0439 (6)
H15A	1.1866	0.5514	0.3888	0.053*
C16	1.0128 (3)	0.5832 (2)	0.32324 (10)	0.0353 (5)
H16A	1.0190	0.5106	0.3037	0.042*
O1	0.82023 (19)	0.97230 (15)	0.12019 (7)	0.0423 (4)
C17	0.7099 (3)	0.9617 (2)	0.06768 (11)	0.0468 (6)
H17A	0.6123	0.9899	0.0752	0.056*
H17B	0.7000	0.8790	0.0546	0.056*
C18	0.7656 (4)	1.0369 (3)	0.02202 (13)	0.0787 (11)
H18A	0.8276	0.9902	−0.0008	0.094*
H18B	0.6818	1.0708	−0.0052	0.094*
C19	0.8545 (4)	1.1309 (3)	0.05549 (13)	0.0722 (10)
H19A	0.7920	1.1998	0.0607	0.087*
H19B	0.9367	1.1561	0.0353	0.087*
C20	0.9134 (3)	1.0744 (3)	0.11416 (13)	0.0583 (8)
H20A	1.0177	1.0501	0.1154	0.070*
H20B	0.9086	1.1306	0.1464	0.070*
O2	1.05983 (17)	0.92400 (14)	0.22785 (7)	0.0410 (4)
C21	1.1375 (3)	1.0270 (2)	0.25374 (14)	0.0536 (7)
H21A	1.0687	1.0799	0.2702	0.064*
H21B	1.1828	1.0707	0.2242	0.064*
C22	1.2562 (3)	0.9807 (3)	0.30188 (13)	0.0604 (8)
H22A	1.2199	0.9798	0.3400	0.072*
H22B	1.3465	1.0297	0.3055	0.072*
C23	1.2880 (3)	0.8548 (3)	0.28236 (12)	0.0537 (7)
H23A	1.3900	0.8484	0.2734	0.064*
H23B	1.2752	0.7971	0.3131	0.064*
C24	1.1725 (3)	0.8350 (2)	0.22683 (13)	0.0484 (7)
H24A	1.2191	0.8431	0.1913	0.058*
H24B	1.1287	0.7557	0.2272	0.058*
Li1	0.8324 (4)	0.9069 (3)	0.20475 (16)	0.0318 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0337 (10)	0.0220 (9)	0.0226 (9)	−0.0014 (7)	0.0017 (7)	0.0000 (7)
N2	0.0503 (12)	0.0271 (11)	0.0270 (10)	−0.0071 (9)	0.0003 (9)	0.0000 (8)
C1	0.0315 (11)	0.0201 (11)	0.0256 (11)	−0.0048 (8)	0.0032 (9)	0.0043 (8)
C2	0.0326 (11)	0.0240 (11)	0.0263 (11)	−0.0037 (9)	0.0024 (9)	0.0003 (9)
C3	0.0450 (14)	0.0339 (13)	0.0259 (11)	−0.0031 (11)	0.0017 (10)	−0.0015 (10)
C4	0.0389 (13)	0.0428 (15)	0.0336 (13)	−0.0054 (11)	−0.0093 (10)	0.0024 (11)
C5	0.0276 (12)	0.0389 (14)	0.0459 (14)	0.0019 (10)	−0.0001 (11)	0.0075 (11)
C6	0.0348 (12)	0.0287 (12)	0.0328 (12)	0.0000 (9)	0.0085 (10)	0.0037 (9)
C7	0.0346 (12)	0.0381 (14)	0.0285 (12)	0.0019 (10)	−0.0005 (10)	−0.0062 (10)
C8	0.0416 (15)	0.0586 (19)	0.092 (2)	−0.0031 (13)	0.0209 (15)	0.0061 (17)
C9	0.0477 (16)	0.0440 (17)	0.076 (2)	0.0047 (12)	0.0121 (14)	−0.0142 (15)
C10	0.0299 (11)	0.0214 (11)	0.0268 (11)	0.0011 (9)	0.0064 (9)	−0.0011 (9)
C11	0.0325 (11)	0.0270 (11)	0.0221 (10)	−0.0028 (9)	0.0077 (9)	0.0039 (9)
C12	0.0439 (13)	0.0307 (13)	0.0268 (12)	0.0006 (10)	0.0038 (10)	0.0013 (10)
C13	0.0592 (16)	0.0409 (15)	0.0288 (13)	−0.0076 (12)	0.0047 (12)	−0.0076 (11)
C14	0.0464 (15)	0.0642 (19)	0.0264 (13)	−0.0109 (13)	−0.0045 (11)	0.0019 (12)
C15	0.0385 (13)	0.0557 (17)	0.0356 (13)	0.0061 (12)	−0.0004 (11)	0.0103 (12)
C16	0.0410 (13)	0.0334 (13)	0.0313 (12)	0.0041 (10)	0.0055 (10)	0.0007 (10)
O1	0.0513 (10)	0.0399 (10)	0.0341 (9)	−0.0082 (8)	0.0021 (8)	0.0080 (7)
C17	0.0528 (16)	0.0504 (16)	0.0353 (14)	0.0010 (12)	0.0008 (12)	0.0040 (12)
C18	0.122 (3)	0.067 (2)	0.0427 (17)	−0.020 (2)	−0.0027 (18)	0.0141 (16)
C19	0.102 (3)	0.055 (2)	0.0587 (19)	−0.0173 (18)	0.0107 (18)	0.0198 (16)
C20	0.0610 (18)	0.0545 (18)	0.0586 (18)	−0.0171 (14)	0.0075 (14)	0.0131 (14)
O2	0.0341 (9)	0.0326 (9)	0.0543 (10)	−0.0038 (7)	0.0013 (8)	−0.0070 (8)
C21	0.0435 (15)	0.0383 (16)	0.077 (2)	−0.0079 (12)	0.0025 (14)	−0.0143 (14)
C22	0.0594 (18)	0.065 (2)	0.0521 (17)	−0.0164 (15)	−0.0043 (14)	−0.0059 (15)
C23	0.0451 (15)	0.0635 (19)	0.0538 (17)	0.0090 (13)	0.0118 (13)	0.0156 (15)
C24	0.0408 (14)	0.0408 (15)	0.0657 (18)	0.0005 (12)	0.0153 (13)	−0.0104 (13)
Li1	0.036 (2)	0.0263 (19)	0.0323 (19)	−0.0019 (15)	0.0032 (16)	−0.0009 (15)

Geometric parameters (Å, º)

Li1—O1	2.040 (4)	C13—C14	1.377 (4)
Li1—O2	2.032 (4)	C13—H13A	0.9300
Li1—N1	2.059 (4)	C14—C15	1.379 (4)
Li1—N2^i	2.028 (4)	C14—H14A	0.9300
N1—C10	1.336 (3)	C15—C16	1.375 (3)
N1—C1	1.422 (3)	C15—H15A	0.9300
N2—Li1^ii	2.028 (4)	C16—H16A	0.9300
N2—C10	1.313 (3)	O1—C17	1.427 (3)
N2—H2	0.8600	O1—C20	1.433 (3)
C1—C6	1.397 (3)	C17—C18	1.481 (4)
C1—C2	1.408 (3)	C17—H17A	0.9700
C2—C3	1.388 (3)	C17—H17B	0.9700
C2—C7	1.517 (3)	C18—C19	1.457 (4)
C3—C4	1.382 (3)	C18—H18A	0.9700
C3—H3A	0.9300	C18—H18B	0.9700
C4—C5	1.375 (3)	C19—C20	1.492 (4)
C4—H4A	0.9300	C19—H19A	0.9700
C5—C6	1.381 (3)	C19—H19B	0.9700
C5—H5A	0.9300	C20—H20A	0.9700
C6—H6A	0.9300	C20—H20B	0.9700
C7—C8	1.514 (4)	O2—C24	1.420 (3)
C7—C9	1.519 (3)	O2—C21	1.423 (3)
C7—H7A	0.9800	C21—C22	1.491 (4)
C8—H8A	0.9600	C21—H21A	0.9700
C8—H8B	0.9600	C21—H21B	0.9700
C8—H8C	0.9600	C22—C23	1.516 (4)
C9—H9A	0.9600	C22—H22A	0.9700
C9—H9B	0.9600	C22—H22B	0.9700
C9—H9C	0.9600	C23—C24	1.515 (4)
C10—C11	1.497 (3)	C23—H23A	0.9700
C11—C16	1.386 (3)	C23—H23B	0.9700
C11—C12	1.388 (3)	C24—H24A	0.9700
C12—C13	1.381 (3)	C24—H24B	0.9700
C12—H12A	0.9300
C10—N1—C1	114.84 (17)	C11—C16—H16A	119.5
C10—N1—Li1	135.78 (17)	C17—O1—C20	108.86 (19)
C1—N1—Li1	108.78 (16)	C17—O1—Li1	133.00 (18)
C10—N2—Li1^ii	138.55 (18)	C20—O1—Li1	115.47 (18)
C10—N2—H2	110.7	O1—C17—C18	105.7 (2)
Li1^ii—N2—H2	110.7	O1—C17—H17A	110.6
C6—C1—C2	118.65 (19)	C18—C17—H17A	110.6
C6—C1—N1	118.65 (19)	O1—C17—H17B	110.6
C2—C1—N1	122.65 (18)	C18—C17—H17B	110.6
C3—C2—C1	118.4 (2)	H17A—C17—H17B	108.7
C3—C2—C7	120.76 (19)	C19—C18—C17	105.2 (2)
C1—C2—C7	120.76 (18)	C19—C18—H18A	110.7
C4—C3—C2	122.2 (2)	C17—C18—H18A	110.7
C4—C3—H3A	118.9	C19—C18—H18B	110.7
C2—C3—H3A	118.9	C17—C18—H18B	110.7
C5—C4—C3	119.4 (2)	H18A—C18—H18B	108.8
C5—C4—H4A	120.3	C18—C19—C20	104.3 (2)
C3—C4—H4A	120.3	C18—C19—H19A	110.9
C4—C5—C6	119.7 (2)	C20—C19—H19A	110.9
C4—C5—H5A	120.1	C18—C19—H19B	110.9
C6—C5—H5A	120.1	C20—C19—H19B	110.9
C5—C6—C1	121.6 (2)	H19A—C19—H19B	108.9
C5—C6—H6A	119.2	O1—C20—C19	107.0 (2)
C1—C6—H6A	119.2	O1—C20—H20A	110.3
C8—C7—C2	111.0 (2)	C19—C20—H20A	110.3
C8—C7—C9	110.6 (2)	O1—C20—H20B	110.3
C2—C7—C9	113.43 (19)	C19—C20—H20B	110.3
C8—C7—H7A	107.2	H20A—C20—H20B	108.6
C2—C7—H7A	107.2	C24—O2—C21	105.70 (18)
C9—C7—H7A	107.2	C24—O2—Li1	128.10 (17)
C7—C8—H8A	109.5	C21—O2—Li1	125.99 (18)
C7—C8—H8B	109.5	O2—C21—C22	105.5 (2)
H8A—C8—H8B	109.5	O2—C21—H21A	110.6
C7—C8—H8C	109.5	C22—C21—H21A	110.6
H8A—C8—H8C	109.5	O2—C21—H21B	110.6
H8B—C8—H8C	109.5	C22—C21—H21B	110.6
C7—C9—H9A	109.5	H21A—C21—H21B	108.8
C7—C9—H9B	109.5	C21—C22—C23	104.7 (2)
H9A—C9—H9B	109.5	C21—C22—H22A	110.8
C7—C9—H9C	109.5	C23—C22—H22A	110.8
H9A—C9—H9C	109.5	C21—C22—H22B	110.8
H9B—C9—H9C	109.5	C23—C22—H22B	110.8
N2—C10—N1	129.43 (19)	H22A—C22—H22B	108.9
N2—C10—C11	115.41 (18)	C24—C23—C22	104.0 (2)
N1—C10—C11	115.16 (18)	C24—C23—H23A	110.9
C16—C11—C12	118.2 (2)	C22—C23—H23A	110.9
C16—C11—C10	120.31 (19)	C24—C23—H23B	110.9
C12—C11—C10	121.52 (19)	C22—C23—H23B	110.9
C13—C12—C11	120.7 (2)	H23A—C23—H23B	109.0
C13—C12—H12A	119.6	O2—C24—C23	106.2 (2)
C11—C12—H12A	119.6	O2—C24—H24A	110.5
C14—C13—C12	120.3 (2)	C23—C24—H24A	110.5
C14—C13—H13A	119.8	O2—C24—H24B	110.5
C12—C13—H13A	119.8	C23—C24—H24B	110.5
C13—C14—C15	119.4 (2)	H24A—C24—H24B	108.7
C13—C14—H14A	120.3	N2^i—Li1—O2	100.25 (17)
C15—C14—H14A	120.3	N2^i—Li1—O1	110.93 (18)
C16—C15—C14	120.3 (2)	O2—Li1—O1	96.36 (17)
C16—C15—H15A	119.8	N2^i—Li1—N1	123.90 (19)
C14—C15—H15A	119.8	O2—Li1—N1	109.33 (18)
C15—C16—C11	121.0 (2)	O1—Li1—N1	111.73 (18)
C15—C16—H16A	119.5

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