1-Chloro­mercurio-2-{(2-chloro­phen­yl)[(3-chloro­phen­yl)imino]meth­yl}ferrocene

The title compound, [FeHg(C₅H₅)(C₁₈H₁₁Cl₂N)Cl], was prepared by the reaction of [(2-chloro­phen­yl)(3-chloro­phenyl­imino)meth­yl]ferrocene, mercury acetate and lithium chloride. The N...Hg separation of 2.884 (5) Å suggests a weak coordination inter­action.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.011 Å
• Disorder in main residue
• R factor = 0.035
• wR factor = 0.094
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Cl3    ..  Cl2'    ..       3.03 Ang.

Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C17
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C20
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C21
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C6'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C7'
PLAT301_ALERT_3_C Main Residue  Disorder .........................      19.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         11
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      25.60 Deg.
              C2'  -C1   -C2      1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  11 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
   9 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

1-Chloromercurio-2-{(2-chlorophenyl)[(3-chlorophenyl)imino]methyl}ferrocene

Crystal data

[FeHg(C5H5)(C18H11Cl2N)Cl]	Z = 2
Mr = 669.16	F(000) = 636
Triclinic, P1	Dx = 2.016 Mg m^−3
Hall symbol: -P 1	Melting point: 502 K
a = 8.5489 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1426 (18) Å	Cell parameters from 3094 reflections
c = 15.213 (3) Å	θ = 2.6–26.3°
α = 90.700 (3)°	µ = 7.99 mm^−1
β = 102.656 (3)°	T = 294 K
γ = 107.516 (3)°	Prism, purple
V = 1102.5 (4) Å^3	0.24 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3842 independent reflections
Radiation source: fine-focus sealed tube	3057 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.175, Tmax = 0.238	k = −10→10
5596 measured reflections	l = −17→18

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.049P)^2 + 0.0748P] where P = (Fo^2 + 2Fc^2)/3
3842 reflections	(Δ/σ)max = 0.001
296 parameters	Δρmax = 1.16 e Å^−3
48 restraints	Δρmin = −1.62 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	Occ. (<1)
Hg1	0.23996 (3)	0.52897 (3)	0.454982 (16)	0.05932 (13)
Fe1	0.18853 (11)	0.16683 (10)	0.34247 (6)	0.0485 (2)
Cl1	0.1268 (3)	0.7202 (3)	0.47773 (15)	0.0852 (6)
Cl3	0.0749 (4)	0.8072 (4)	0.02571 (17)	0.1172 (10)
N1	0.3678 (7)	0.5798 (6)	0.2938 (3)	0.0484 (13)
C1	0.4146 (7)	0.4636 (7)	0.2838 (4)	0.0415 (14)
Cl2	0.7932 (3)	0.5377 (3)	0.3022 (2)	0.0839 (10)	0.886 (6)
C2	0.4716 (6)	0.4258 (6)	0.2012 (3)	0.0465 (18)	0.886 (6)
C3	0.6420 (5)	0.4544 (3)	0.2046 (3)	0.057 (2)	0.886 (6)
C4	0.6927 (6)	0.4159 (7)	0.1291 (4)	0.076 (3)	0.886 (6)
H4A	0.8068	0.4351	0.1313	0.091*	0.886 (6)
C5	0.5729 (9)	0.3489 (7)	0.0501 (4)	0.084 (3)	0.886 (6)
H5A	0.6068	0.3232	−0.0004	0.101*	0.886 (6)
C6	0.4025 (8)	0.3203 (6)	0.0467 (3)	0.075 (3)	0.886 (6)
H6A	0.3223	0.2755	−0.0061	0.090*	0.886 (6)
C7	0.3518 (5)	0.3587 (6)	0.1223 (3)	0.055 (2)	0.886 (6)
H7A	0.2377	0.3396	0.1200	0.066*	0.886 (6)
C8	0.3801 (8)	0.6937 (7)	0.2314 (4)	0.0442 (14)
C9	0.5306 (9)	0.8093 (8)	0.2352 (5)	0.0620 (19)
H9	0.6275	0.8098	0.2776	0.074*
C10	0.5372 (11)	0.9220 (9)	0.1773 (6)	0.081 (3)
H10	0.6385	1.0002	0.1821	0.098*
C11	0.3999 (12)	0.9240 (9)	0.1126 (6)	0.075 (2)
H11	0.4069	1.0002	0.0724	0.091*
C12	0.2516 (10)	0.8100 (9)	0.1087 (5)	0.063 (2)
C13	0.2376 (9)	0.6949 (8)	0.1670 (5)	0.0556 (17)
H13	0.1347	0.6194	0.1633	0.067*
C14	0.3992 (7)	0.3502 (7)	0.3518 (4)	0.0482 (16)
C15	0.3312 (8)	0.3574 (8)	0.4311 (4)	0.0558 (19)
C16	0.3300 (9)	0.2185 (10)	0.4719 (5)	0.070 (2)
H16	0.2923	0.1911	0.5240	0.084*
C17	0.3932 (10)	0.1287 (10)	0.4230 (7)	0.082 (3)
H17	0.4035	0.0328	0.4370	0.099*
C18	0.4393 (8)	0.2088 (8)	0.3477 (6)	0.0620 (19)
H18	0.4862	0.1757	0.3045	0.074*
C19	−0.0583 (9)	0.1627 (9)	0.3149 (5)	0.064 (2)
H19	−0.1009	0.2304	0.3410	0.077*
C20	−0.0414 (10)	0.0219 (10)	0.3476 (6)	0.082 (3)
H20	−0.0705	−0.0199	0.3995	0.099*
C21	0.0269 (12)	−0.0416 (9)	0.2875 (7)	0.085 (3)
H21	0.0511	−0.1342	0.2922	0.102*
C22	0.0526 (10)	0.0559 (9)	0.2197 (6)	0.074 (2)
H22	0.0972	0.0402	0.1712	0.088*
C23	0.0013 (8)	0.1797 (8)	0.2362 (5)	0.0555 (17)
H23	0.0056	0.2620	0.2005	0.067*
Cl2'	0.276 (2)	0.340 (3)	0.0924 (12)	0.066 (7)	0.114 (6)
C2'	0.5439 (17)	0.456 (5)	0.2322 (13)	0.0465 (18)	0.114 (6)
C3'	0.492 (2)	0.396 (5)	0.1423 (14)	0.067 (18)	0.114 (6)
C4'	0.610 (3)	0.392 (6)	0.0938 (17)	0.06 (2)	0.114 (6)
H4'A	0.5755	0.3520	0.0336	0.068*	0.114 (6)
C5'	0.781 (3)	0.447 (6)	0.135 (2)	0.07 (2)	0.114 (6)
H5'A	0.8609	0.4435	0.1026	0.089*	0.114 (6)
C6'	0.8337 (17)	0.506 (5)	0.225 (2)	0.08 (2)	0.114 (6)
H6'A	0.9481	0.5427	0.2526	0.092*	0.114 (6)
C7'	0.7149 (18)	0.511 (5)	0.2735 (16)	0.042 (15)	0.114 (6)
H7'A	0.7498	0.5504	0.3336	0.050*	0.114 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Hg1	0.05557 (19)	0.0682 (2)	0.03406 (16)	−0.00550 (13)	0.00393 (12)	0.00479 (12)
Fe1	0.0403 (5)	0.0450 (5)	0.0475 (5)	0.0033 (4)	−0.0022 (4)	0.0160 (4)
Cl1	0.0920 (16)	0.0927 (15)	0.0673 (13)	0.0203 (13)	0.0228 (12)	0.0106 (12)
Cl3	0.115 (2)	0.162 (3)	0.0745 (16)	0.079 (2)	−0.0276 (14)	0.0088 (16)
N1	0.052 (3)	0.047 (3)	0.043 (3)	0.011 (3)	0.011 (2)	0.011 (2)
C1	0.030 (3)	0.043 (3)	0.041 (3)	0.003 (3)	−0.002 (2)	0.008 (3)
Cl2	0.0407 (14)	0.0865 (17)	0.111 (2)	0.0121 (12)	0.0002 (13)	0.0263 (15)
C2	0.046 (4)	0.041 (4)	0.053 (4)	0.014 (3)	0.013 (3)	0.021 (3)
C3	0.055 (5)	0.046 (4)	0.076 (6)	0.021 (4)	0.021 (4)	0.026 (4)
C4	0.081 (9)	0.074 (6)	0.099 (8)	0.044 (6)	0.047 (7)	0.032 (6)
C5	0.128 (10)	0.067 (6)	0.087 (9)	0.044 (6)	0.066 (8)	0.023 (6)
C6	0.113 (8)	0.062 (5)	0.055 (5)	0.032 (5)	0.025 (5)	0.017 (4)
C7	0.064 (7)	0.058 (6)	0.045 (6)	0.020 (6)	0.013 (5)	0.007 (5)
C8	0.054 (4)	0.039 (3)	0.041 (3)	0.018 (3)	0.009 (3)	0.005 (3)
C9	0.045 (4)	0.052 (4)	0.073 (5)	0.004 (3)	−0.004 (3)	0.014 (4)
C10	0.077 (6)	0.056 (5)	0.091 (6)	0.001 (4)	0.006 (5)	0.022 (4)
C11	0.101 (7)	0.054 (4)	0.069 (5)	0.025 (5)	0.013 (5)	0.026 (4)
C12	0.073 (5)	0.077 (5)	0.043 (4)	0.044 (4)	−0.006 (4)	0.001 (4)
C13	0.046 (4)	0.061 (4)	0.052 (4)	0.012 (3)	0.000 (3)	0.000 (3)
C14	0.035 (3)	0.055 (4)	0.042 (4)	0.002 (3)	−0.002 (3)	0.017 (3)
C15	0.038 (3)	0.060 (4)	0.038 (4)	−0.017 (3)	−0.015 (3)	0.016 (3)
C16	0.054 (5)	0.083 (5)	0.046 (4)	−0.006 (4)	−0.007 (3)	0.031 (4)
C17	0.062 (5)	0.076 (5)	0.094 (7)	0.016 (4)	−0.009 (5)	0.055 (5)
C18	0.040 (4)	0.064 (4)	0.076 (5)	0.014 (3)	0.005 (3)	0.030 (4)
C19	0.038 (4)	0.078 (5)	0.058 (5)	0.000 (3)	−0.004 (3)	−0.007 (4)
C20	0.053 (5)	0.086 (6)	0.069 (5)	−0.026 (4)	0.000 (4)	0.025 (5)
C21	0.082 (6)	0.046 (4)	0.102 (7)	0.002 (4)	−0.004 (5)	0.000 (5)
C22	0.071 (5)	0.074 (5)	0.058 (5)	0.010 (4)	−0.004 (4)	−0.008 (4)
C23	0.044 (4)	0.057 (4)	0.053 (4)	0.011 (3)	−0.007 (3)	0.003 (3)
Cl2'	0.041 (11)	0.085 (12)	0.042 (11)	−0.011 (9)	−0.009 (8)	−0.006 (9)
C2'	0.046 (4)	0.041 (4)	0.053 (4)	0.014 (3)	0.013 (3)	0.021 (3)
C3'	0.07 (2)	0.07 (2)	0.07 (2)	0.021 (11)	0.020 (11)	0.009 (10)
C4'	0.06 (2)	0.06 (2)	0.06 (2)	0.018 (11)	0.015 (11)	0.004 (10)
C5'	0.07 (3)	0.07 (3)	0.07 (3)	0.022 (12)	0.018 (11)	0.006 (10)
C6'	0.08 (2)	0.08 (2)	0.07 (2)	0.022 (11)	0.018 (11)	0.010 (10)
C7'	0.040 (17)	0.043 (17)	0.042 (17)	0.013 (10)	0.009 (10)	0.001 (10)

Geometric parameters (Å, º)

Hg1—C15	2.012 (8)	C10—H10	0.9300
Hg1—Cl1	2.294 (3)	C11—C12	1.367 (11)
Fe1—C21	2.027 (8)	C11—H11	0.9300
Fe1—C17	2.030 (8)	C12—C13	1.379 (10)
Fe1—C20	2.032 (7)	C13—H13	0.9300
Fe1—C14	2.035 (6)	C14—C18	1.438 (10)
Fe1—C16	2.038 (7)	C14—C15	1.459 (10)
Fe1—C22	2.039 (8)	C15—C16	1.418 (10)
Fe1—C23	2.043 (7)	C16—C17	1.395 (13)
Fe1—C18	2.045 (7)	C16—H16	0.9300
Fe1—C19	2.048 (7)	C17—C18	1.432 (11)
Fe1—C15	2.070 (6)	C17—H17	0.9300
Cl3—C12	1.737 (7)	C18—H18	0.9300
N1—C1	1.262 (8)	C19—C23	1.394 (10)
N1—C8	1.413 (8)	C19—C20	1.422 (11)
C1—C14	1.471 (8)	C19—H19	0.9300
C1—C2'	1.507 (16)	C20—C21	1.392 (13)
C1—C2	1.515 (7)	C20—H20	0.9300
Cl2—C3	1.731 (5)	C21—C22	1.382 (12)
C2—C3	1.3900	C21—H21	0.9300
C2—C7	1.3900	C22—C23	1.369 (10)
C3—C4	1.3900	C22—H22	0.9300
C4—C5	1.3900	C23—H23	0.9300
C4—H4A	0.9300	Cl2'—C3'	1.745 (10)
C5—C6	1.3900	C2'—C3'	1.3900
C5—H5A	0.9300	C2'—C7'	1.3900
C6—C7	1.3900	C3'—C4'	1.3900
C6—H6A	0.9300	C4'—C5'	1.3900
C7—H7A	0.9300	C4'—H4'A	0.9300
C8—C9	1.386 (9)	C5'—C6'	1.3900
C8—C13	1.389 (9)	C5'—H5'A	0.9300
C9—C10	1.360 (10)	C6'—C7'	1.3900
C9—H9	0.9300	C6'—H6'A	0.9300
C10—C11	1.361 (11)	C7'—H7'A	0.9300
C15—Hg1—Cl1	177.75 (17)	C11—C12—Cl3	118.9 (6)
C21—Fe1—C17	107.0 (4)	C13—C12—Cl3	118.6 (6)
C21—Fe1—C20	40.1 (4)	C12—C13—C8	118.7 (6)
C17—Fe1—C20	117.0 (3)	C12—C13—H13	120.6
C21—Fe1—C14	153.1 (4)	C8—C13—H13	120.6
C17—Fe1—C14	68.9 (3)	C18—C14—C15	108.7 (6)
C20—Fe1—C14	165.9 (4)	C18—C14—C1	125.3 (6)
C21—Fe1—C16	126.5 (4)	C15—C14—C1	125.9 (6)
C17—Fe1—C16	40.1 (4)	C18—C14—Fe1	69.7 (4)
C20—Fe1—C16	107.3 (3)	C15—C14—Fe1	70.5 (3)
C14—Fe1—C16	68.4 (3)	C1—C14—Fe1	122.9 (4)
C21—Fe1—C22	39.7 (3)	C16—C15—C14	105.4 (7)
C17—Fe1—C22	127.5 (4)	C16—C15—Hg1	133.1 (6)
C20—Fe1—C22	67.2 (4)	C14—C15—Hg1	121.1 (5)
C14—Fe1—C22	120.5 (3)	C16—C15—Fe1	68.6 (4)
C16—Fe1—C22	164.1 (4)	C14—C15—Fe1	67.9 (4)
C21—Fe1—C23	66.5 (3)	Hg1—C15—Fe1	122.0 (3)
C17—Fe1—C23	165.3 (4)	C17—C16—C15	110.7 (7)
C20—Fe1—C23	67.4 (3)	C17—C16—Fe1	69.6 (5)
C14—Fe1—C23	110.4 (3)	C15—C16—Fe1	71.0 (4)
C16—Fe1—C23	154.4 (4)	C17—C16—H16	124.7
C22—Fe1—C23	39.2 (3)	C15—C16—H16	124.7
C21—Fe1—C18	118.0 (4)	Fe1—C16—H16	126.3
C17—Fe1—C18	41.1 (3)	C16—C17—C18	108.6 (7)
C20—Fe1—C18	151.1 (4)	C16—C17—Fe1	70.2 (5)
C14—Fe1—C18	41.3 (3)	C18—C17—Fe1	70.0 (4)
C16—Fe1—C18	68.5 (3)	C16—C17—H17	125.7
C22—Fe1—C18	108.6 (4)	C18—C17—H17	125.7
C23—Fe1—C18	128.7 (3)	Fe1—C17—H17	125.7
C21—Fe1—C19	67.5 (4)	C17—C18—C14	106.6 (7)
C17—Fe1—C19	151.9 (4)	C17—C18—Fe1	68.9 (4)
C20—Fe1—C19	40.8 (3)	C14—C18—Fe1	69.0 (4)
C14—Fe1—C19	128.6 (3)	C17—C18—H18	126.7
C16—Fe1—C19	119.5 (3)	C14—C18—H18	126.7
C22—Fe1—C19	66.9 (3)	Fe1—C18—H18	127.0
C23—Fe1—C19	39.8 (3)	C23—C19—C20	106.7 (8)
C18—Fe1—C19	166.3 (3)	C23—C19—Fe1	69.9 (4)
C21—Fe1—C15	163.7 (4)	C20—C19—Fe1	69.0 (4)
C17—Fe1—C15	68.7 (4)	C23—C19—H19	126.6
C20—Fe1—C15	126.5 (4)	C20—C19—H19	126.6
C14—Fe1—C15	41.6 (3)	Fe1—C19—H19	126.0
C16—Fe1—C15	40.4 (3)	C21—C20—C19	107.1 (7)
C22—Fe1—C15	154.9 (3)	C21—C20—Fe1	69.8 (5)
C23—Fe1—C15	121.2 (3)	C19—C20—Fe1	70.2 (4)
C18—Fe1—C15	69.8 (3)	C21—C20—H20	126.5
C19—Fe1—C15	108.4 (3)	C19—C20—H20	126.5
C1—N1—C8	121.7 (5)	Fe1—C20—H20	125.2
N1—C1—C14	118.7 (6)	C22—C21—C20	108.6 (8)
N1—C1—C2'	125.1 (18)	C22—C21—Fe1	70.6 (4)
C14—C1—C2'	111.8 (17)	C20—C21—Fe1	70.1 (4)
N1—C1—C2	123.7 (5)	C22—C21—H21	125.7
C14—C1—C2	117.4 (5)	C20—C21—H21	125.7
C2'—C1—C2	25.6 (6)	Fe1—C21—H21	125.2
C3—C2—C7	120.0	C23—C22—C21	108.4 (8)
C3—C2—C1	120.5 (3)	C23—C22—Fe1	70.6 (4)
C7—C2—C1	119.5 (3)	C21—C22—Fe1	69.7 (5)
C2—C3—C4	120.0	C23—C22—H22	125.8
C2—C3—Cl2	120.7 (3)	C21—C22—H22	125.8
C4—C3—Cl2	119.3 (3)	Fe1—C22—H22	125.6
C5—C4—C3	120.0	C22—C23—C19	109.2 (7)
C5—C4—H4A	120.0	C22—C23—Fe1	70.2 (4)
C3—C4—H4A	120.0	C19—C23—Fe1	70.3 (4)
C6—C5—C4	120.0	C22—C23—H23	125.4
C6—C5—H5A	120.0	C19—C23—H23	125.4
C4—C5—H5A	120.0	Fe1—C23—H23	125.7
C5—C6—C7	120.0	C3'—C2'—C7'	120.0
C5—C6—H6A	120.0	C3'—C2'—C1	119.7 (8)
C7—C6—H6A	120.0	C7'—C2'—C1	120.3 (8)
C6—C7—C2	120.0	C2'—C3'—C4'	120.0
C6—C7—H7A	120.0	C2'—C3'—Cl2'	117.7 (11)
C2—C7—H7A	120.0	C4'—C3'—Cl2'	122.2 (11)
C9—C8—C13	118.7 (6)	C5'—C4'—C3'	120.0
C9—C8—N1	121.4 (6)	C5'—C4'—H4'A	120.0
C13—C8—N1	119.8 (6)	C3'—C4'—H4'A	120.0
C10—C9—C8	120.3 (7)	C4'—C5'—C6'	120.0
C10—C9—H9	119.9	C4'—C5'—H5'A	120.0
C8—C9—H9	119.9	C6'—C5'—H5'A	120.0
C9—C10—C11	122.0 (7)	C7'—C6'—C5'	120.0
C9—C10—H10	119.0	C7'—C6'—H6'A	120.0
C11—C10—H10	119.0	C5'—C6'—H6'A	120.0
C10—C11—C12	117.7 (7)	C6'—C7'—C2'	120.0
C10—C11—H11	121.1	C6'—C7'—H7'A	120.0
C12—C11—H11	121.1	C2'—C7'—H7'A	120.0
C11—C12—C13	122.5 (7)