3,3′-Bis(2,4-dichloro­phenoxy­acet­yl)-1,1′-(2,2′-dimethyl­biphenyl-4,4′-di­yl)dithio­urea N,N-dimethyl­formamide disolvate

In the title compound, C₃₂H₂₆Cl₄N₄O₄S₂·2C₃H₇NO, the mol­ecule of 3,3′-bis­(2,4-dichloro­phenoxy­acet­yl)-1,1′-(2,2′-di­meth­yl­biphenyl-4,4′-di­yl)dithio­urea (BT) possesses a crystallographically imposed centre of symmetry at the mid-point of the central C—C bond. Intra­molecular N—H...O and C—H...S hydrogen bonds contribute to the essential planarity of the BT skeleton, with a maximum deviation from the mean plane of 0.196 (2) Å for the S atoms.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in solvent or counterion
• R factor = 0.076
• wR factor = 0.161
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         44 Perc.
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N3
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        N3'
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.42
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C32 H26 Cl4 N4 O4 S2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C3 H7 N O

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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.

3,3'-Bis(2,4-dichlorophenoxyacetyl)-1,1'-(2,2'-dimethylbiphenyl-4,4'- diyl)dithiourea N,N-dimethylformamide disolvate

Crystal data

C32H26Cl4N4O4S2·2C3H7NO	Z = 1
Mr = 882.70	F(000) = 458
Triclinic, P1	Dx = 1.400 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.012 (2) Å	Cell parameters from 25 reflections
b = 10.488 (2) Å	θ = 9–12°
c = 11.124 (2) Å	µ = 0.44 mm^−1
α = 67.78 (3)°	T = 293 K
β = 77.92 (3)°	Prism, yellow
γ = 78.07 (3)°	0.30 × 0.20 × 0.10 mm
V = 1046.8 (4) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	1798 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 26.0°, θmin = 2.1°
ω/2θ scans	h = −11→12
Absorption correction: ψ scan (North et al., 1968)	k = −11→12
Tmin = 0.881, Tmax = 0.958	l = 0→13
4104 measured reflections	3 standard reflections every 200 reflections
4104 independent reflections	intensity decay: none

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.161	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.047P)^2] where P = (Fo^2 + 2Fc^2)/3
4104 reflections	(Δ/σ)max = 0.001
300 parameters	Δρmax = 0.22 e Å^−3
81 restraints	Δρmin = −0.24 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)
Cl1	1.10379 (13)	0.23531 (17)	0.14612 (17)	0.0898 (6)
Cl2	0.60665 (14)	0.54598 (16)	0.09552 (17)	0.0982 (6)
S1	0.09276 (13)	0.60688 (15)	0.20113 (14)	0.0694 (5)
O1	0.5026 (3)	0.3079 (3)	0.2934 (3)	0.0660 (11)
O2	0.2072 (3)	0.1778 (3)	0.4998 (4)	0.0759 (12)
N1	0.2419 (3)	0.3818 (4)	0.3313 (4)	0.0521 (11)
H1A	0.3071	0.4244	0.2776	0.062*
N2	0.0101 (3)	0.3886 (4)	0.4105 (4)	0.0531 (11)
H2A	0.0417	0.3096	0.4641	0.064*
C1	0.9251 (5)	0.2539 (6)	0.1917 (6)	0.0584 (15)
C2	0.8666 (5)	0.1457 (6)	0.2840 (5)	0.0632 (16)
H2B	0.9209	0.0617	0.3216	0.076*
C3	0.7241 (4)	0.1609 (5)	0.3224 (5)	0.0631 (16)
H3A	0.6833	0.0874	0.3870	0.076*
C4	0.6443 (4)	0.2836 (5)	0.2650 (5)	0.0500 (13)
C5	0.7063 (5)	0.3909 (5)	0.1695 (5)	0.0560 (14)
C6	0.8481 (5)	0.3778 (6)	0.1340 (5)	0.0636 (15)
H6A	0.8900	0.4519	0.0719	0.076*
C7	0.4364 (4)	0.2019 (5)	0.3981 (5)	0.0621 (16)
H7A	0.4727	0.1820	0.4786	0.075*
H7B	0.4527	0.1172	0.3780	0.075*
C8	0.2826 (4)	0.2543 (5)	0.4144 (5)	0.0565 (15)
C9	0.1066 (4)	0.4568 (5)	0.3191 (5)	0.0465 (12)
C10	−0.1358 (4)	0.4248 (5)	0.4338 (4)	0.0430 (12)
C11	−0.2087 (4)	0.3241 (5)	0.5275 (4)	0.0454 (12)
C12	−0.3521 (4)	0.3575 (5)	0.5509 (5)	0.0522 (14)
H12A	−0.4023	0.2899	0.6132	0.063*
C13	−0.4236 (4)	0.4857 (5)	0.4864 (5)	0.0443 (12)
C14	−0.3464 (4)	0.5823 (5)	0.3936 (5)	0.0663 (17)
H14A	−0.3906	0.6689	0.3467	0.080*
C15	−0.2028 (4)	0.5528 (5)	0.3682 (5)	0.0649 (16)
H15A	−0.1524	0.6205	0.3064	0.078*
C16	−0.1394 (4)	0.1817 (5)	0.6013 (5)	0.0664 (16)
H16A	−0.0880	0.1387	0.5401	0.100*
H16B	−0.2080	0.1256	0.6581	0.100*
H16C	−0.0779	0.1900	0.6528	0.100*
O3	0.4798 (19)	1.059 (3)	−0.2532 (19)	0.112 (8)	0.552 (10)
N3	0.3106 (13)	0.9633 (15)	−0.0826 (15)	0.074 (4)	0.552 (10)
C17	0.1681 (13)	0.9759 (15)	−0.0276 (13)	0.128 (6)	0.552 (10)
H17A	0.1201	1.0612	−0.0807	0.191*	0.552 (10)
H17B	0.1599	0.9761	0.0599	0.191*	0.552 (10)
H17C	0.1286	0.8988	−0.0252	0.191*	0.552 (10)
C18	0.4072 (17)	0.8476 (16)	−0.0168 (17)	0.135 (6)	0.552 (10)
H18A	0.4992	0.8613	−0.0608	0.203*	0.552 (10)
H18B	0.3860	0.7630	−0.0183	0.203*	0.552 (10)
H18C	0.4005	0.8415	0.0725	0.203*	0.552 (10)
C19	0.3579 (15)	1.0543 (12)	−0.2002 (13)	0.091 (4)	0.552 (10)
H19A	0.2918	1.1202	−0.2465	0.109*	0.552 (10)
O3'	0.501 (2)	1.042 (5)	−0.276 (2)	0.117 (9)	0.448 (10)
C17'	0.2511 (19)	1.0859 (19)	−0.1396 (19)	0.133 (7)	0.448 (10)
H17D	0.2877	1.1509	−0.2215	0.199*	0.448 (10)
H17E	0.2104	1.1338	−0.0795	0.199*	0.448 (10)
H17F	0.1822	1.0439	−0.1541	0.199*	0.448 (10)
N3'	0.3622 (17)	0.978 (2)	−0.085 (2)	0.078 (6)	0.448 (10)
C19'	0.4837 (18)	0.9633 (19)	−0.1593 (17)	0.099 (6)	0.448 (10)
H19B	0.5547	0.8950	−0.1243	0.119*	0.448 (10)
C18'	0.324 (2)	0.873 (2)	0.0403 (19)	0.142 (8)	0.448 (10)
H18D	0.4037	0.8069	0.0671	0.213*	0.448 (10)
H18E	0.2555	0.8256	0.0318	0.213*	0.448 (10)
H18F	0.2865	0.9157	0.1049	0.213*	0.448 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0357 (7)	0.1138 (14)	0.1264 (15)	−0.0080 (8)	0.0093 (8)	−0.0618 (12)
Cl2	0.0600 (9)	0.0809 (12)	0.1116 (14)	−0.0031 (8)	−0.0174 (9)	0.0122 (10)
S1	0.0463 (7)	0.0692 (10)	0.0670 (10)	−0.0047 (7)	−0.0022 (7)	−0.0003 (8)
O1	0.0294 (16)	0.067 (2)	0.079 (3)	−0.0030 (16)	0.0064 (17)	−0.011 (2)
O2	0.0409 (19)	0.057 (2)	0.093 (3)	0.0008 (17)	0.0061 (19)	0.001 (2)
N1	0.032 (2)	0.055 (3)	0.057 (3)	−0.0072 (18)	0.0042 (18)	−0.011 (2)
N2	0.036 (2)	0.045 (2)	0.063 (3)	−0.0046 (18)	0.0026 (19)	−0.007 (2)
C1	0.036 (3)	0.071 (4)	0.076 (4)	−0.008 (3)	0.006 (3)	−0.042 (3)
C2	0.039 (3)	0.064 (4)	0.085 (4)	0.010 (3)	−0.008 (3)	−0.033 (3)
C3	0.039 (3)	0.052 (3)	0.080 (4)	0.005 (2)	0.000 (3)	−0.012 (3)
C4	0.034 (2)	0.053 (3)	0.059 (3)	−0.001 (2)	−0.001 (2)	−0.020 (3)
C5	0.046 (3)	0.060 (3)	0.055 (3)	−0.005 (3)	−0.006 (3)	−0.014 (3)
C6	0.044 (3)	0.071 (4)	0.072 (4)	−0.022 (3)	0.006 (3)	−0.020 (3)
C7	0.036 (3)	0.055 (3)	0.076 (4)	−0.003 (2)	0.003 (3)	−0.009 (3)
C8	0.034 (3)	0.057 (4)	0.065 (4)	−0.004 (2)	0.003 (3)	−0.013 (3)
C9	0.039 (2)	0.045 (3)	0.053 (3)	−0.007 (2)	0.001 (2)	−0.018 (3)
C10	0.029 (2)	0.041 (3)	0.055 (3)	0.003 (2)	−0.001 (2)	−0.020 (3)
C11	0.036 (2)	0.040 (3)	0.048 (3)	0.001 (2)	−0.005 (2)	−0.008 (2)
C12	0.032 (2)	0.058 (3)	0.059 (3)	−0.008 (2)	−0.001 (2)	−0.016 (3)
C13	0.035 (2)	0.043 (3)	0.053 (3)	0.001 (2)	−0.006 (2)	−0.018 (2)
C14	0.038 (3)	0.043 (3)	0.088 (4)	0.003 (2)	−0.002 (3)	0.002 (3)
C15	0.038 (3)	0.042 (3)	0.085 (4)	0.000 (2)	0.009 (3)	−0.002 (3)
C16	0.042 (3)	0.056 (3)	0.077 (4)	0.000 (2)	−0.008 (3)	−0.001 (3)
O3	0.118 (9)	0.084 (9)	0.111 (12)	−0.015 (8)	0.010 (8)	−0.022 (11)
N3	0.106 (8)	0.046 (6)	0.072 (7)	−0.031 (7)	−0.021 (7)	−0.007 (5)
C17	0.134 (9)	0.119 (11)	0.117 (11)	−0.019 (8)	0.024 (8)	−0.050 (9)
C18	0.170 (12)	0.086 (10)	0.121 (12)	−0.001 (9)	−0.051 (10)	0.001 (8)
C19	0.106 (8)	0.057 (7)	0.088 (9)	0.002 (7)	−0.012 (7)	−0.010 (6)
O3'	0.140 (14)	0.119 (16)	0.092 (9)	−0.033 (11)	0.027 (9)	−0.050 (9)
C17'	0.116 (11)	0.114 (13)	0.130 (13)	−0.005 (9)	0.008 (10)	−0.019 (10)
N3'	0.078 (8)	0.085 (11)	0.077 (9)	−0.042 (7)	0.000 (7)	−0.025 (7)
C19'	0.100 (9)	0.099 (12)	0.094 (10)	−0.019 (8)	0.008 (8)	−0.039 (9)
C18'	0.147 (15)	0.117 (13)	0.112 (12)	−0.031 (11)	0.017 (10)	0.003 (9)

Geometric parameters (Å, º)

Cl1—C1	1.745 (5)	C13—C14	1.374 (6)
Cl2—C5	1.726 (5)	C13—C13^i	1.486 (8)
S1—C9	1.626 (5)	C14—C15	1.399 (6)
O1—C4	1.380 (5)	C14—H14A	0.9300
O1—C7	1.426 (5)	C15—H15A	0.9300
O2—C8	1.220 (5)	C16—H16A	0.9600
N1—C8	1.344 (6)	C16—H16B	0.9600
N1—C9	1.424 (5)	C16—H16C	0.9600
N1—H1A	0.8600	O3—C19	1.242 (10)
N2—C9	1.342 (5)	N3—C19	1.352 (15)
N2—C10	1.425 (5)	N3—C17	1.430 (13)
N2—H2A	0.8600	N3—C18	1.443 (15)
C1—C2	1.352 (7)	C17—H17A	0.9600
C1—C6	1.363 (6)	C17—H17B	0.9600
C2—C3	1.395 (6)	C17—H17C	0.9600
C2—H2B	0.9300	C18—H18A	0.9600
C3—C4	1.367 (6)	C18—H18B	0.9600
C3—H3A	0.9300	C18—H18C	0.9600
C4—C5	1.374 (6)	C19—H19A	0.9300
C5—C6	1.385 (6)	O3'—C19'	1.247 (10)
C6—H6A	0.9300	C17'—N3'	1.46 (2)
C7—C8	1.521 (6)	C17'—H17D	0.9600
C7—H7A	0.9700	C17'—H17E	0.9600
C7—H7B	0.9700	C17'—H17F	0.9600
C10—C15	1.369 (6)	N3'—C19'	1.34 (2)
C10—C11	1.380 (5)	N3'—C18'	1.45 (3)
C11—C12	1.399 (5)	C19'—H19B	0.9300
C11—C16	1.506 (6)	C18'—H18D	0.9600
C12—C13	1.387 (6)	C18'—H18E	0.9600
C12—H12A	0.9300	C18'—H18F	0.9600
C4—O1—C7	117.4 (4)	C13—C14—C15	121.3 (4)
C8—N1—C9	129.6 (4)	C13—C14—H14A	119.4
C8—N1—H1A	115.2	C15—C14—H14A	119.4
C9—N1—H1A	115.2	C10—C15—C14	120.4 (4)
C9—N2—C10	131.0 (4)	C10—C15—H15A	119.8
C9—N2—H2A	114.5	C14—C15—H15A	119.8
C10—N2—H2A	114.5	C11—C16—H16A	109.5
C2—C1—C6	121.6 (4)	C11—C16—H16B	109.5
C2—C1—Cl1	119.4 (4)	H16A—C16—H16B	109.5
C6—C1—Cl1	119.1 (4)	C11—C16—H16C	109.5
C1—C2—C3	119.5 (5)	H16A—C16—H16C	109.5
C1—C2—H2B	120.2	H16B—C16—H16C	109.5
C3—C2—H2B	120.2	C19—N3—C17	121.5 (13)
C4—C3—C2	120.0 (5)	C19—N3—C18	117.9 (14)
C4—C3—H3A	120.0	C17—N3—C18	120.5 (13)
C2—C3—H3A	120.0	N3—C17—H17A	109.5
C3—C4—C5	119.2 (4)	N3—C17—H17B	109.5
C3—C4—O1	124.5 (4)	H17A—C17—H17B	109.5
C5—C4—O1	116.2 (4)	N3—C17—H17C	109.5
C4—C5—C6	120.9 (5)	H17A—C17—H17C	109.5
C4—C5—Cl2	119.7 (4)	H17B—C17—H17C	109.5
C6—C5—Cl2	119.3 (4)	N3—C18—H18A	109.5
C1—C6—C5	118.6 (5)	N3—C18—H18B	109.5
C1—C6—H6A	120.7	H18A—C18—H18B	109.5
C5—C6—H6A	120.7	N3—C18—H18C	109.5
O1—C7—C8	107.8 (4)	H18A—C18—H18C	109.5
O1—C7—H7A	110.1	H18B—C18—H18C	109.5
C8—C7—H7A	110.1	O3—C19—N3	127.1 (14)
O1—C7—H7B	110.1	O3—C19—H19A	116.4
C8—C7—H7B	110.1	N3—C19—H19A	116.4
H7A—C7—H7B	108.5	N3'—C17'—H17D	109.5
O2—C8—N1	125.8 (4)	N3'—C17'—H17E	109.5
O2—C8—C7	118.0 (4)	H17D—C17'—H17E	109.5
N1—C8—C7	116.3 (4)	N3'—C17'—H17F	109.5
N2—C9—N1	112.4 (4)	H17D—C17'—H17F	109.5
N2—C9—S1	130.7 (4)	H17E—C17'—H17F	109.5
N1—C9—S1	116.8 (3)	C19'—N3'—C18'	122 (2)
C15—C10—C11	120.5 (4)	C19'—N3'—C17'	120.2 (18)
C15—C10—N2	122.8 (4)	C18'—N3'—C17'	116.2 (18)
C11—C10—N2	116.7 (4)	O3'—C19'—N3'	119 (2)
C10—C11—C12	117.5 (4)	O3'—C19'—H19B	120.3
C10—C11—C16	122.3 (4)	N3'—C19'—H19B	120.3
C12—C11—C16	120.2 (4)	N3'—C18'—H18D	109.5
C13—C12—C11	123.7 (4)	N3'—C18'—H18E	109.5
C13—C12—H12A	118.2	H18D—C18'—H18E	109.5
C11—C12—H12A	118.2	N3'—C18'—H18F	109.5
C14—C13—C12	116.6 (4)	H18D—C18'—H18F	109.5
C14—C13—C13^i	122.1 (5)	H18E—C18'—H18F	109.5
C12—C13—C13^i	121.2 (5)
C6—C1—C2—C3	−0.6 (9)	C8—N1—C9—N2	3.7 (7)
Cl1—C1—C2—C3	178.9 (4)	C8—N1—C9—S1	−176.4 (4)
C1—C2—C3—C4	1.2 (8)	C9—N2—C10—C15	−7.5 (8)
C2—C3—C4—C5	0.1 (8)	C9—N2—C10—C11	172.8 (5)
C2—C3—C4—O1	178.2 (5)	C15—C10—C11—C12	0.8 (7)
C7—O1—C4—C3	6.0 (7)	N2—C10—C11—C12	−179.5 (4)
C7—O1—C4—C5	−175.9 (5)	C15—C10—C11—C16	179.6 (5)
C3—C4—C5—C6	−2.1 (8)	N2—C10—C11—C16	−0.7 (7)
O1—C4—C5—C6	179.7 (5)	C10—C11—C12—C13	−0.7 (7)
C3—C4—C5—Cl2	179.5 (4)	C16—C11—C12—C13	−179.5 (5)
O1—C4—C5—Cl2	1.3 (7)	C11—C12—C13—C14	1.0 (8)
C2—C1—C6—C5	−1.3 (8)	C11—C12—C13—C13^i	178.8 (6)
Cl1—C1—C6—C5	179.2 (4)	C12—C13—C14—C15	−1.4 (8)
C4—C5—C6—C1	2.7 (8)	C13^i—C13—C14—C15	−179.2 (6)
Cl2—C5—C6—C1	−178.9 (4)	C11—C10—C15—C14	−1.2 (8)
C4—O1—C7—C8	177.7 (4)	N2—C10—C15—C14	179.1 (5)
C9—N1—C8—O2	−1.5 (9)	C13—C14—C15—C10	1.6 (9)
C9—N1—C8—C7	177.8 (5)	C17—N3—C19—O3	175 (3)
O1—C7—C8—O2	179.8 (5)	C18—N3—C19—O3	−9 (3)
O1—C7—C8—N1	0.5 (7)	C18'—N3'—C19'—O3'	165 (3)
C10—N2—C9—N1	−179.8 (4)	C17'—N3'—C19'—O3'	0 (4)
C10—N2—C9—S1	0.3 (8)

Symmetry code: (i) −x−1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	2.09	2.558 (5)	114
N2—H2A···O2	0.86	1.93	2.669 (5)	143
C15—H15A···S1	0.93	2.49	3.182 (5)	131
C18—H18A···O3	0.96	2.36	2.80 (3)	107