(R)-2,2′-Bis[N′-(3,5-dichloro­phen­yl)ureido]-1,1′-binaphthalene chloro­form disolvate

Holakovský, R.; Pojarová, M.; Dušek, M.; Čejka, J.; Císařová, I.

doi:10.1107/S1600536810052657

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages o384-o385

doi:10.1107/S1600536810052657

Open

access

(R)-2,2′-Bis[N′-(3,5-dichlorophenyl)ureido]-1,1′-binaphthalene chloroform disolvate

Roman Holakovský,^a ^* Michaela Pojarová,^b Michal Dušek,^b Jan Čejka ^c and Ivana Císařová ^d

^aDepartment of Organic Chemistry, Institute of Chemical Technology Prague, Technická 5, 166 28 Prague 6, Czech Republic, ^bInstitute of Physics, AS CR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic, ^cDepartment of Solid State Chemistry, Institute of Chemical Technology Prague, Technická 5, 166 28 Prague 6, Czech Republic, and ^dCharles University in Prague, Faculty of Science - Department of Inorganic Chemistry, Hlavova 2030/8, 128 43 Prague 2, Czech Republic
^*Correspondence e-mail: roman.holakovsky@vscht.cz

(Received 20 November 2010; accepted 15 December 2010; online 15 January 2011)

The title compound, C₃₄H₂₂Cl₄N₄O₂·2CHCl₃, is a new urea based on the 1,1′-binaphthalene skeleton, which crystallizes with two molecules of binaphthalene and four molecules of chloroform in the unit cell. The chloroform solvent molecules do not participate in non-covalent interactions and therefore, can be found in several positions. The binaphthalene molecules are connected via a system of N—H⋯O hydrogen bonds between the ureido units. C—H⋯O interactions also occur. In contrast to unsubstituted urea, where molecules form squares in crystals, the bulky substituents disturb this arrangement and three ureido groups form infinite chains, while the fourth interacts with a neighbouring binaphthalene ring via an N—H⋯π interaction. The solvent molecules are disordered with occupancy ratios of 0.60:0.40, 0.58:0.42, 0.50:0.50 and 0.77:0.23.

Related literature

For background to 1,1′-binaphthalene derivatives and their use in molecular recognition and catalysis, see: Pu (1998 ); Telfer & Kuroda (2003 ). For applications of urea derivatives based on the binaphthalene skeleton in chiral recognition, see: Stibor et al. (2004 ) and for their applications in the field of organocatalysis, see: Takemoto (2005 ); Fleming et al. (2006 ); Liu et al. (2007 ); Shi & Liu (2008 ); Harada et al. (2009 ). For the structure of urea, see: Sklar et al. (1961 ).

Experimental

Crystal data

C₃₄H₂₂Cl₄N₄O₂·2CHCl₃
M_r = 899.09
Triclinic, P 1
a = 11.879 (2) Å
b = 12.445 (3) Å
c = 15.039 (3) Å
α = 96.71 (3)°
β = 110.90 (3)°
γ = 103.98 (3)°
V = 1964.4 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.75 mm⁻¹
T = 150 K
0.4 × 0.12 × 0.10 mm

Data collection

Bruker SMART 1000 diffractometer
20566 measured reflections
16629 independent reflections
13656 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.125
S = 1.03
16629 reflections
993 parameters
51 restraints
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.58 e Å⁻³
Absolute structure: Flack (1983 ), 7535 Friedel pairs
Flack parameter: −0.01 (4)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C56–C61 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O4ⁱ	0.86	2.16	2.897 (3)	144
N4—H4A⋯O4ⁱ	0.86	2.05	2.821 (3)	149
N5—H5A⋯O2	0.86	2.11	2.821 (3)	139
N6—H6A⋯O2	0.86	2.17	2.947 (3)	150
N7—H7A⋯O3	0.86	2.36	2.955 (3)	126
N8—H8A⋯O3	0.86	2.26	3.030 (3)	149
C38—H38⋯O1ⁱⁱ	0.93	2.41	3.304 (4)	162
C54—H54⋯O4	0.93	2.32	2.893 (3)	120
C200—H200⋯O1ⁱⁱ	0.98	2.15	3.035 (7)	149
C300—H300⋯O3	0.98	2.52	3.315 (9)	138
N2—H2A⋯Cg1	0.86	2.59	3.300 (3)	141
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052657/om2383sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810052657/om2383Isup2.hkl

checkCIF report

Comment top

The title compound (Figs. 1 and 2) is a new urea based on 1,1'-binaphthalene skeleton. Because of their highly stable chiral configuration, the 2,2'-substituted 1,1'-binaphthyls have demonstrated outstanding chiral discrimination properties (Pu, 1998). Urea was prepared from (R)-1,1'-binaphthyl-2,2'-diamine by reaction with 3,5-dichlorophenyl isocyanate. Such molecule could be used as a ligand for chiral recognition of anions (Stibor et al., 2004). The unit cell contains two molecules of substituted urea which are connected via system of intra- (N7—H7A···O3; N8—H8A···O3) and intermolecular hydrogen bonds (N3—H3A···O4; N4—H4A···O4; N5—H5A···O2; N6—H6A···O2) among three of four ureido moieties. Hydrogen bonds are listed in Table 1. The fourth ureido group interacts with the neighbouring binaphthalene ring in a N—H···π interaction (distance between N2—H2A and the center of aromatic ring C56-C61 is 2.587 (3) Å). In contrast to unsubstituted urea molecules, which form infinite straight chains perpendicular to each other in direction of c axis (Sklar et al., 1961), the substitution with bulk substituents disturbs this arrangement and the hydrogen bonds form infinite wavy chains along the b axis (Fig. 3).

Related literature top

For background to 1,1'-binaphthalene derivatives and their use in molecular recognition and catalysis, see: Pu (1998); Telfer et al. (2003). For applications of urea derivatives based on the binaphthalene skeleton in chiral recognition, see: Stibor et al. (2004) and for their applications in the field of organocatalysis, see: Takemoto (2005); Fleming et al. (2006); Liu et al. (2007); Shi et al. (2008); Harada et al. (2009). For the structure of urea, see: Sklar et al. (1961).

Experimental top

(R)-1,1'-Binaphthyl-2,2'-diamine (150 mg, 0.53 mmol) in dry dichloromethane (45 ml) was treated with 3,5-dichlorophenyl isocyanate (800 mg, 4,26 mmol, 4 eq per amino group) at ambient temperature for 12 h. The reaction was quenched with methanol (10 ml) and stirred for another 12 h. The reaction mixture was evaporated in vacuo and purified by column chromatography (silica gel, dichloromethane) to give the title compound as a white solid (97% yield). Single crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of CDCl₃ solution over a period of several days.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. View of the one molecule of (R)-2,2'-bis[N-(3,5- dichlorophenyl)ureido]-1,1'-binaphthalene together with atom-labeling scheme. The hydrogen atoms which do not participate in hydrogen bonds and the solvents molecules were omitted for better clarity. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. View of the other molecule of (R)-2,2'-bis[N-(3,5- dichlorophenyl)ureido]-1,1'-binaphthalene together with atom-labeling scheme. The hydrogen atoms which do not participate in hydrogen bonds and the solvents molecules were omitted for better clarity. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 3. Projection in direction of the c axis with hydrogen bonds indicated.

(R)-2,2'-Bis[N'-(3,5-dichlorophenyl)ureido]-1,1'-binaphthalene chloroform disolvate top

Crystal data top

C₃₄H₂₂Cl₄N₄O₂·2CHCl₃	Z = 2
M_r = 899.09	F(000) = 908
Triclinic, P1	D_x = 1.520 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.879 (2) Å	Cell parameters from 16629 reflections
b = 12.445 (3) Å	θ = 1.7–27.6°
c = 15.039 (3) Å	µ = 0.75 mm⁻¹
α = 96.71 (3)°	T = 150 K
β = 110.90 (3)°	Plates, colourless
γ = 103.98 (3)°	0.4 × 0.12 × 0.10 mm
V = 1964.4 (9) Å³

Data collection top

Bruker SMART 1000 diffractometer	13656 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 27.6°, θ_min = 1.7°
ω scans	h = −15→15
20566 measured reflections	k = −16→16
16629 independent reflections	l = −19→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0525P)² + 1.6951P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.040
16629 reflections	Δρ_max = 0.63 e Å⁻³
993 parameters	Δρ_min = −0.58 e Å⁻³
51 restraints	Absolute structure: Flack (1983), 7535 Friedel pairs
0 constraints	Absolute structure parameter: −0.01 (4)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₃₄H₂₂Cl₄N₄O₂·2CHCl₃	γ = 103.98 (3)°
M_r = 899.09	V = 1964.4 (9) Å³
Triclinic, P1	Z = 2
a = 11.879 (2) Å	Mo Kα radiation
b = 12.445 (3) Å	µ = 0.75 mm⁻¹
c = 15.039 (3) Å	T = 150 K
α = 96.71 (3)°	0.4 × 0.12 × 0.10 mm
β = 110.90 (3)°

Data collection top

Bruker SMART 1000 diffractometer	13656 reflections with I > 2σ(I)
20566 measured reflections	R_int = 0.037
16629 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.125	Δρ_max = 0.63 e Å⁻³
S = 1.03	Δρ_min = −0.58 e Å⁻³
16629 reflections	Absolute structure: Flack (1983), 7535 Friedel pairs
993 parameters	Absolute structure parameter: −0.01 (4)
51 restraints

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.26222 (7)	0.20014 (6)	0.38434 (6)	0.04304 (19)
Cl2	−0.18934 (8)	0.26670 (8)	0.31225 (7)	0.0613 (2)
Cl3	0.19698 (7)	0.50494 (6)	0.49404 (5)	0.04183 (18)
Cl4	0.37139 (10)	0.95394 (8)	0.65451 (6)	0.0624 (3)
O1	0.00094 (17)	0.57167 (15)	0.16079 (14)	0.0331 (4)
O2	0.35517 (17)	0.63877 (15)	0.25092 (13)	0.0295 (4)
N1	0.0937 (2)	0.57038 (19)	0.05171 (17)	0.0331 (5)
H1A	0.1373	0.5364	0.0307	0.040*
N2	0.0982 (2)	0.43829 (19)	0.14486 (17)	0.0319 (5)
H2A	0.1398	0.4156	0.1140	0.038*
N3	0.3489 (2)	0.77884 (18)	0.16653 (15)	0.0269 (5)
H3A	0.3421	0.8460	0.1661	0.032*
N4	0.3253 (2)	0.80211 (18)	0.31075 (16)	0.0291 (5)
H4A	0.3222	0.8683	0.3010	0.035*
C1	0.1508 (2)	0.7245 (2)	−0.02232 (19)	0.0264 (6)
C2	0.0655 (2)	0.6619 (2)	0.00973 (19)	0.0285 (6)
C3	−0.0502 (3)	0.6840 (2)	−0.0042 (2)	0.0347 (7)
H3	−0.1056	0.6425	0.0191	0.042*
C4	−0.0803 (3)	0.7666 (3)	−0.0520 (2)	0.0377 (7)
H4	−0.1563	0.7810	−0.0604	0.045*
C5	0.0009 (3)	0.8303 (2)	−0.0887 (2)	0.0335 (7)
C6	−0.0311 (3)	0.9125 (3)	−0.1431 (2)	0.0417 (8)
H6	−0.1081	0.9260	−0.1542	0.050*
C7	0.0474 (3)	0.9714 (3)	−0.1791 (2)	0.0447 (8)
H7	0.0239	1.0241	−0.2151	0.054*
C8	0.1652 (3)	0.9530 (2)	−0.1621 (2)	0.0407 (8)
H8	0.2194	0.9942	−0.1865	0.049*
C9	0.2002 (3)	0.8757 (2)	−0.1105 (2)	0.0350 (7)
H9	0.2787	0.8655	−0.0990	0.042*
C10	0.1188 (3)	0.8101 (2)	−0.07356 (19)	0.0291 (6)
C11	0.0591 (2)	0.5303 (2)	0.1218 (2)	0.0291 (6)
C12	0.0774 (2)	0.3766 (2)	0.2139 (2)	0.0282 (6)
C13	−0.0334 (3)	0.3594 (2)	0.2302 (2)	0.0335 (6)
H13	−0.0941	0.3932	0.1995	0.040*
C14	−0.0502 (3)	0.2912 (3)	0.2930 (2)	0.0368 (7)
C15	0.0374 (3)	0.2386 (3)	0.3409 (2)	0.0360 (7)
H15	0.0235	0.1919	0.3823	0.043*
C16	0.1472 (3)	0.2598 (2)	0.3232 (2)	0.0310 (6)
C17	0.1677 (2)	0.3270 (2)	0.2606 (2)	0.0281 (6)
H17	0.2417	0.3390	0.2499	0.034*
C18	0.2721 (2)	0.6984 (2)	−0.00653 (18)	0.0245 (6)
C19	0.3648 (2)	0.7205 (2)	0.08680 (19)	0.0277 (6)
C20	0.4754 (2)	0.6888 (2)	0.1046 (2)	0.0299 (6)
H20	0.5366	0.7053	0.1679	0.036*
C21	0.4927 (2)	0.6340 (2)	0.0293 (2)	0.0307 (6)
H21	0.5657	0.6127	0.0419	0.037*
C22	0.4023 (2)	0.6087 (2)	−0.06752 (19)	0.0288 (6)
C23	0.4167 (3)	0.5474 (3)	−0.1467 (2)	0.0374 (7)
H23	0.4886	0.5245	−0.1351	0.045*
C24	0.3276 (3)	0.5223 (3)	−0.2383 (2)	0.0435 (8)
H24	0.3387	0.4825	−0.2893	0.052*
C25	0.2184 (3)	0.5556 (3)	−0.2573 (2)	0.0362 (7)
H25	0.1576	0.5375	−0.3209	0.043*
C26	0.1997 (3)	0.6143 (2)	−0.1841 (2)	0.0322 (6)
H26	0.1267	0.6360	−0.1982	0.039*
C27	0.2910 (2)	0.6425 (2)	−0.08664 (19)	0.0275 (6)
C28	0.3440 (2)	0.7334 (2)	0.24307 (18)	0.0241 (6)
C29	0.3106 (2)	0.7745 (2)	0.39504 (19)	0.0267 (6)
C30	0.2615 (2)	0.6638 (2)	0.40074 (19)	0.0283 (6)
H30	0.2361	0.6035	0.3480	0.034*
C31	0.2512 (2)	0.6454 (2)	0.4867 (2)	0.0305 (6)
C32	0.2831 (3)	0.7321 (3)	0.5661 (2)	0.0346 (7)
H32	0.2730	0.7178	0.6226	0.042*
C33	0.3309 (3)	0.8411 (3)	0.5570 (2)	0.0400 (8)
C34	0.3465 (3)	0.8651 (2)	0.4750 (2)	0.0326 (7)
H34	0.3800	0.9397	0.4720	0.039*
Cl5	0.57394 (13)	0.34425 (10)	0.69746 (8)	0.0873 (3)
Cl6	0.60915 (9)	0.78573 (9)	0.73187 (6)	0.0607 (3)
Cl7	0.73123 (14)	0.08571 (9)	0.71486 (7)	0.0854 (4)
Cl8	0.69612 (8)	−0.20657 (7)	0.40606 (7)	0.0537 (2)
O3	0.58803 (17)	0.40229 (15)	0.37528 (13)	0.0305 (4)
O4	0.38945 (18)	0.01114 (15)	0.25737 (14)	0.0315 (5)
N5	0.47199 (19)	0.46681 (18)	0.24838 (15)	0.0259 (5)
H5A	0.4076	0.4909	0.2261	0.031*
N6	0.4839 (2)	0.52764 (19)	0.40193 (16)	0.0320 (6)
H6A	0.4352	0.5656	0.3741	0.038*
N7	0.4394 (2)	0.18812 (18)	0.22683 (16)	0.0277 (5)
H7A	0.5038	0.2464	0.2402	0.033*
N8	0.5607 (2)	0.15267 (19)	0.36835 (16)	0.0308 (6)
H8A	0.5976	0.2248	0.3857	0.037*
C35	0.4606 (2)	0.3404 (2)	0.10734 (18)	0.0247 (6)
C36	0.5279 (2)	0.4320 (2)	0.18452 (18)	0.0248 (6)
C37	0.6511 (2)	0.4978 (2)	0.2005 (2)	0.0274 (6)
H37	0.6955	0.5590	0.2540	0.033*
C38	0.7056 (2)	0.4725 (2)	0.1385 (2)	0.0313 (6)
H38	0.7868	0.5163	0.1497	0.038*
C39	0.6394 (2)	0.3800 (2)	0.0573 (2)	0.0306 (6)
C40	0.6942 (3)	0.3511 (3)	−0.0096 (2)	0.0384 (7)
H40	0.7750	0.3947	0.0003	0.046*
C41	0.6301 (3)	0.2610 (3)	−0.0869 (2)	0.0467 (8)
H41	0.6669	0.2431	−0.1295	0.056*
C42	0.5080 (3)	0.1948 (3)	−0.1025 (2)	0.0459 (8)
H42	0.4648	0.1332	−0.1558	0.055*
C43	0.4513 (3)	0.2185 (3)	−0.0415 (2)	0.0357 (7)
H43	0.3702	0.1735	−0.0536	0.043*
C44	0.5155 (2)	0.3116 (2)	0.04026 (19)	0.0282 (6)
C45	0.5200 (2)	0.4621 (2)	0.34418 (19)	0.0257 (6)
C46	0.5201 (2)	0.5380 (2)	0.5033 (2)	0.0316 (6)
C47	0.5281 (3)	0.4448 (3)	0.5451 (2)	0.0400 (7)
H47	0.5087	0.3732	0.5068	0.048*
C48	0.5655 (3)	0.4610 (3)	0.6453 (2)	0.0496 (8)
C49	0.5941 (3)	0.5648 (4)	0.7049 (2)	0.0521 (9)
H49	0.6217	0.5743	0.7723	0.062*
C50	0.5800 (3)	0.6546 (3)	0.6602 (2)	0.0431 (8)
C51	0.5458 (2)	0.6426 (3)	0.5610 (2)	0.0328 (7)
H51	0.5401	0.7050	0.5331	0.039*
C52	0.3332 (2)	0.2647 (2)	0.09375 (18)	0.0242 (6)
C53	0.3265 (2)	0.1840 (2)	0.14977 (18)	0.0257 (6)
C54	0.2083 (2)	0.1063 (2)	0.1341 (2)	0.0293 (6)
H54	0.2051	0.0504	0.1699	0.035*
C55	0.1008 (3)	0.1138 (2)	0.0669 (2)	0.0326 (7)
H55	0.0240	0.0622	0.0571	0.039*
C56	0.1008 (3)	0.1980 (2)	0.0108 (2)	0.0301 (6)
C57	−0.0113 (3)	0.2103 (3)	−0.0556 (2)	0.0394 (8)
H57	−0.0890	0.1631	−0.0624	0.047*
C58	−0.0077 (3)	0.2909 (3)	−0.1105 (2)	0.0457 (9)
H58	−0.0825	0.2986	−0.1537	0.055*
C59	0.1091 (3)	0.3610 (3)	−0.1008 (2)	0.0402 (8)
H59	0.1112	0.4134	−0.1400	0.048*
C60	0.2204 (3)	0.3545 (2)	−0.0352 (2)	0.0319 (7)
H60	0.2969	0.4037	−0.0289	0.038*
C61	0.2197 (2)	0.2725 (2)	0.02373 (19)	0.0272 (6)
C62	0.4579 (2)	0.1102 (2)	0.28235 (19)	0.0274 (6)
C63	0.6103 (3)	0.0830 (2)	0.4313 (2)	0.0318 (7)
C64	0.6429 (3)	0.1150 (3)	0.5305 (2)	0.0409 (8)
H64	0.6321	0.1813	0.5567	0.049*
C65	0.6920 (3)	0.0463 (3)	0.5902 (2)	0.0459 (9)
C66	0.7090 (3)	−0.0520 (3)	0.5542 (2)	0.0418 (8)
H66	0.7421	−0.0969	0.5954	0.050*
C67	0.6757 (3)	−0.0823 (2)	0.4553 (2)	0.0370 (7)
C68	0.6273 (3)	−0.0162 (2)	0.3914 (2)	0.0357 (7)
H68	0.6071	−0.0374	0.3249	0.043*
Cl10	0.53490 (16)	0.01074 (15)	0.09971 (13)	0.0546 (4)	0.60
Cl12	0.79357 (19)	0.0613 (2)	0.11063 (18)	0.0980 (7)	0.60
Cl11	0.5872 (2)	−0.0818 (3)	−0.06273 (18)	0.0971 (8)	0.60
C100	0.6370 (5)	0.0287 (5)	0.0408 (4)	0.0498 (12)	0.60
H100	0.6287	0.0959	0.0141	0.060*	0.60
Cl13	0.5597 (3)	−0.0111 (3)	0.1169 (2)	0.0546 (4)	0.40
Cl14	0.7862 (4)	0.0531 (4)	0.0786 (3)	0.0971 (8)	0.40
Cl15	0.5513 (3)	−0.0905 (4)	−0.0699 (3)	0.0980 (7)	0.40
C101	0.6412 (7)	−0.0388 (8)	0.0563 (6)	0.0498 (12)	0.40
H101	0.6623	−0.1056	0.0774	0.060*	0.40
Cl20	0.82035 (18)	0.77629 (17)	0.17030 (17)	0.0558 (4)	0.58
Cl21	0.96509 (17)	0.73874 (16)	0.35521 (16)	0.0570 (3)	0.58
Cl22	1.0749 (2)	0.92854 (18)	0.2861 (2)	0.0697 (3)	0.58
C200	0.9738 (6)	0.7888 (5)	0.2535 (5)	0.0436 (9)	0.58
H200	1.0083	0.7401	0.2214	0.052*	0.58
Cl23	0.8182 (3)	0.7926 (3)	0.1869 (3)	0.0558 (4)	0.42
Cl25	1.0739 (4)	0.9381 (3)	0.2815 (4)	0.0697 (3)	0.42
Cl24	0.9869 (3)	0.7649 (3)	0.3707 (2)	0.0570 (3)	0.42
C201	0.9742 (9)	0.8007 (8)	0.2597 (7)	0.0436 (9)	0.42
H201	1.0011	0.7477	0.2245	0.052*	0.42
Cl30	0.9302 (4)	0.5635 (5)	0.5023 (3)	0.1098 (6)	0.50
Cl31	0.8503 (3)	0.4372 (3)	0.6273 (4)	0.1080 (6)	0.50
Cl32	0.8902 (3)	0.6767 (4)	0.6599 (3)	0.0959 (5)	0.50
C300	0.8422 (8)	0.5524 (7)	0.5724 (6)	0.0608 (11)	0.50
H300	0.7537	0.5393	0.5291	0.073*	0.50
Cl33	0.9259 (4)	0.5540 (6)	0.5012 (4)	0.1098 (6)	0.50
Cl35	0.8991 (4)	0.6884 (4)	0.6568 (3)	0.0959 (5)	0.50
Cl34	0.8638 (4)	0.4516 (4)	0.6438 (4)	0.1080 (6)	0.50
C301	0.8468 (9)	0.5568 (8)	0.5774 (7)	0.0608 (11)	0.50
H301	0.7567	0.5407	0.5370	0.073*	0.50
Cl40	1.01580 (19)	0.25846 (16)	0.58778 (16)	0.0958 (5)	0.77
Cl41	1.0437 (2)	0.03823 (16)	0.54162 (17)	0.1061 (7)	0.77
Cl42	1.22528 (18)	0.20149 (14)	0.71565 (12)	0.0890 (5)	0.77
C400	1.1179 (9)	0.1762 (6)	0.6000 (6)	0.134 (4)	0.77
H400	1.1683	0.2055	0.5638	0.161*	0.77
Cl45	1.2546 (6)	0.2198 (5)	0.6413 (4)	0.0890 (5)	0.23
C401	1.1031 (13)	0.1494 (12)	0.6348 (17)	0.134 (4)	0.23
H401	1.1074	0.1547	0.7015	0.161*	0.23
Cl44	1.0423 (9)	0.0034 (6)	0.5739 (6)	0.1061 (7)	0.23
Cl43	0.9875 (7)	0.2056 (6)	0.5716 (6)	0.0958 (5)	0.23

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0427 (4)	0.0395 (4)	0.0477 (4)	0.0165 (3)	0.0133 (3)	0.0198 (3)
Cl2	0.0496 (4)	0.0799 (5)	0.0815 (5)	0.0243 (4)	0.0457 (3)	0.0451 (4)
Cl3	0.0580 (4)	0.0343 (3)	0.0356 (3)	0.0058 (3)	0.0260 (3)	0.0109 (3)
Cl4	0.0915 (6)	0.0462 (5)	0.0404 (4)	0.0106 (4)	0.0293 (4)	−0.0117 (3)
O1	0.0415 (9)	0.0286 (9)	0.0408 (10)	0.0159 (7)	0.0249 (8)	0.0119 (7)
O2	0.0394 (9)	0.0275 (9)	0.0306 (9)	0.0168 (7)	0.0181 (7)	0.0121 (7)
N1	0.0406 (10)	0.0318 (11)	0.0442 (12)	0.0189 (9)	0.0285 (9)	0.0178 (9)
N2	0.0420 (11)	0.0303 (11)	0.0394 (11)	0.0171 (9)	0.0285 (9)	0.0141 (9)
N3	0.0360 (10)	0.0231 (10)	0.0264 (10)	0.0133 (8)	0.0143 (8)	0.0086 (8)
N4	0.0440 (11)	0.0229 (10)	0.0278 (10)	0.0145 (9)	0.0193 (9)	0.0068 (8)
C1	0.0282 (11)	0.0272 (12)	0.0254 (12)	0.0093 (10)	0.0112 (9)	0.0079 (9)
C2	0.0335 (12)	0.0275 (12)	0.0284 (12)	0.0125 (10)	0.0132 (10)	0.0115 (10)
C3	0.0298 (12)	0.0396 (15)	0.0393 (14)	0.0121 (11)	0.0161 (11)	0.0147 (12)
C4	0.0333 (13)	0.0417 (15)	0.0447 (16)	0.0194 (11)	0.0164 (12)	0.0145 (12)
C5	0.0397 (14)	0.0302 (13)	0.0298 (13)	0.0132 (11)	0.0110 (11)	0.0076 (11)
C6	0.0462 (15)	0.0392 (15)	0.0406 (16)	0.0223 (13)	0.0112 (13)	0.0128 (12)
C7	0.0562 (17)	0.0340 (14)	0.0431 (16)	0.0216 (13)	0.0111 (14)	0.0173 (12)
C8	0.0500 (17)	0.0290 (14)	0.0355 (15)	0.0063 (13)	0.0101 (13)	0.0139 (11)
C9	0.0381 (14)	0.0295 (13)	0.0334 (14)	0.0066 (11)	0.0114 (12)	0.0099 (11)
C10	0.0380 (13)	0.0235 (12)	0.0265 (12)	0.0124 (10)	0.0111 (10)	0.0071 (10)
C11	0.0253 (12)	0.0224 (12)	0.0383 (14)	0.0019 (10)	0.0150 (11)	0.0060 (10)
C12	0.0323 (12)	0.0220 (12)	0.0302 (12)	0.0047 (10)	0.0150 (10)	0.0050 (10)
C13	0.0326 (12)	0.0355 (14)	0.0392 (14)	0.0118 (11)	0.0196 (11)	0.0130 (11)
C14	0.0325 (12)	0.0400 (15)	0.0465 (15)	0.0093 (11)	0.0246 (11)	0.0172 (12)
C15	0.0404 (14)	0.0360 (15)	0.0321 (13)	0.0073 (12)	0.0171 (11)	0.0107 (11)
C16	0.0343 (13)	0.0261 (12)	0.0320 (13)	0.0092 (10)	0.0119 (11)	0.0083 (10)
C17	0.0276 (11)	0.0231 (12)	0.0345 (13)	0.0039 (10)	0.0164 (10)	0.0043 (10)
C18	0.0266 (11)	0.0240 (11)	0.0246 (11)	0.0071 (9)	0.0109 (9)	0.0111 (9)
C19	0.0340 (12)	0.0267 (12)	0.0272 (12)	0.0113 (10)	0.0142 (10)	0.0126 (9)
C20	0.0269 (12)	0.0332 (13)	0.0288 (12)	0.0096 (10)	0.0081 (10)	0.0128 (10)
C21	0.0317 (12)	0.0361 (13)	0.0336 (13)	0.0149 (10)	0.0179 (10)	0.0163 (10)
C22	0.0326 (12)	0.0292 (12)	0.0306 (12)	0.0106 (10)	0.0165 (10)	0.0137 (10)
C23	0.0454 (14)	0.0459 (16)	0.0358 (13)	0.0210 (12)	0.0265 (11)	0.0167 (11)
C24	0.0533 (16)	0.0521 (18)	0.0334 (14)	0.0181 (14)	0.0257 (13)	0.0086 (13)
C25	0.0359 (14)	0.0426 (16)	0.0267 (13)	0.0057 (12)	0.0129 (11)	0.0067 (11)
C26	0.0371 (13)	0.0336 (13)	0.0278 (13)	0.0126 (11)	0.0119 (11)	0.0131 (10)
C27	0.0336 (12)	0.0260 (12)	0.0263 (12)	0.0079 (10)	0.0148 (10)	0.0112 (9)
C28	0.0253 (11)	0.0241 (12)	0.0220 (11)	0.0078 (9)	0.0081 (9)	0.0053 (9)
C29	0.0289 (12)	0.0244 (12)	0.0272 (12)	0.0088 (10)	0.0111 (10)	0.0056 (9)
C30	0.0309 (12)	0.0294 (13)	0.0245 (12)	0.0080 (10)	0.0121 (10)	0.0052 (10)
C31	0.0305 (12)	0.0333 (13)	0.0294 (13)	0.0098 (11)	0.0128 (10)	0.0103 (10)
C32	0.0378 (13)	0.0385 (15)	0.0269 (13)	0.0070 (12)	0.0158 (11)	0.0051 (11)
C33	0.0456 (15)	0.0397 (16)	0.0288 (14)	0.0096 (13)	0.0137 (12)	−0.0030 (12)
C34	0.0341 (13)	0.0267 (13)	0.0332 (14)	0.0038 (11)	0.0138 (11)	0.0027 (11)
Cl5	0.1306 (8)	0.0989 (6)	0.0758 (5)	0.0560 (6)	0.0630 (5)	0.0646 (5)
Cl6	0.0593 (5)	0.0742 (6)	0.0334 (4)	0.0176 (4)	0.0106 (4)	−0.0131 (4)
Cl7	0.1381 (10)	0.0531 (5)	0.0294 (4)	0.0349 (6)	−0.0080 (5)	0.0004 (4)
Cl8	0.0665 (4)	0.0519 (4)	0.0599 (5)	0.0401 (3)	0.0278 (4)	0.0206 (3)
O3	0.0352 (9)	0.0273 (9)	0.0298 (9)	0.0135 (7)	0.0105 (7)	0.0089 (7)
O4	0.0350 (9)	0.0232 (9)	0.0330 (9)	0.0076 (7)	0.0095 (8)	0.0098 (7)
N5	0.0259 (10)	0.0267 (10)	0.0246 (10)	0.0112 (8)	0.0076 (8)	0.0052 (8)
N6	0.0411 (11)	0.0323 (11)	0.0248 (11)	0.0192 (10)	0.0101 (9)	0.0073 (9)
N7	0.0270 (10)	0.0223 (10)	0.0339 (11)	0.0065 (8)	0.0113 (9)	0.0117 (8)
N8	0.0356 (11)	0.0215 (10)	0.0306 (11)	0.0079 (9)	0.0079 (9)	0.0078 (9)
C35	0.0288 (11)	0.0218 (11)	0.0246 (11)	0.0096 (9)	0.0091 (9)	0.0104 (9)
C36	0.0270 (11)	0.0217 (11)	0.0278 (12)	0.0093 (9)	0.0107 (10)	0.0098 (9)
C37	0.0256 (11)	0.0208 (11)	0.0318 (13)	0.0051 (9)	0.0083 (10)	0.0052 (10)
C38	0.0234 (11)	0.0283 (12)	0.0450 (15)	0.0078 (10)	0.0141 (11)	0.0172 (11)
C39	0.0313 (12)	0.0378 (13)	0.0304 (12)	0.0172 (11)	0.0143 (10)	0.0159 (10)
C40	0.0389 (13)	0.0463 (16)	0.0460 (15)	0.0203 (12)	0.0263 (11)	0.0238 (12)
C41	0.0523 (15)	0.068 (2)	0.0382 (15)	0.0316 (15)	0.0278 (12)	0.0201 (14)
C42	0.0539 (17)	0.0534 (19)	0.0320 (15)	0.0177 (15)	0.0203 (13)	0.0025 (13)
C43	0.0403 (14)	0.0375 (15)	0.0324 (13)	0.0112 (12)	0.0188 (11)	0.0069 (11)
C44	0.0318 (12)	0.0304 (12)	0.0281 (12)	0.0149 (10)	0.0129 (10)	0.0127 (10)
C45	0.0283 (12)	0.0196 (11)	0.0273 (12)	0.0056 (10)	0.0100 (10)	0.0049 (9)
C46	0.0297 (12)	0.0375 (14)	0.0287 (13)	0.0087 (11)	0.0136 (10)	0.0086 (11)
C47	0.0442 (14)	0.0454 (16)	0.0392 (15)	0.0183 (13)	0.0212 (12)	0.0169 (12)
C48	0.0580 (17)	0.067 (2)	0.0463 (16)	0.0307 (15)	0.0325 (13)	0.0316 (14)
C49	0.0508 (16)	0.086 (2)	0.0282 (14)	0.0285 (17)	0.0198 (13)	0.0153 (15)
C50	0.0354 (14)	0.0590 (19)	0.0308 (15)	0.0142 (14)	0.0117 (12)	0.0001 (13)
C51	0.0297 (12)	0.0396 (15)	0.0286 (13)	0.0109 (11)	0.0115 (11)	0.0058 (11)
C52	0.0278 (11)	0.0189 (11)	0.0258 (12)	0.0060 (9)	0.0118 (9)	0.0036 (9)
C53	0.0298 (12)	0.0224 (11)	0.0267 (12)	0.0075 (10)	0.0138 (10)	0.0055 (9)
C54	0.0306 (12)	0.0236 (12)	0.0342 (13)	0.0054 (10)	0.0144 (10)	0.0097 (10)
C55	0.0234 (12)	0.0266 (13)	0.0412 (15)	0.0011 (10)	0.0105 (11)	0.0055 (11)
C56	0.0290 (12)	0.0256 (13)	0.0291 (13)	0.0046 (10)	0.0070 (11)	0.0045 (10)
C57	0.0316 (14)	0.0311 (14)	0.0439 (16)	0.0048 (12)	0.0048 (13)	0.0089 (12)
C58	0.0369 (15)	0.0399 (16)	0.0476 (18)	0.0103 (13)	0.0014 (14)	0.0160 (14)
C59	0.0444 (16)	0.0293 (14)	0.0357 (15)	0.0051 (12)	0.0056 (13)	0.0129 (12)
C60	0.0329 (13)	0.0260 (13)	0.0301 (13)	0.0036 (11)	0.0085 (11)	0.0071 (10)
C61	0.0315 (12)	0.0199 (11)	0.0271 (12)	0.0064 (10)	0.0104 (10)	0.0017 (9)
C62	0.0309 (12)	0.0252 (12)	0.0301 (12)	0.0099 (10)	0.0155 (10)	0.0080 (10)
C63	0.0267 (12)	0.0300 (13)	0.0328 (14)	0.0057 (11)	0.0062 (11)	0.0102 (11)
C64	0.0431 (16)	0.0262 (13)	0.0372 (16)	0.0064 (12)	0.0006 (13)	0.0061 (12)
C65	0.0482 (18)	0.0362 (16)	0.0325 (16)	0.0048 (14)	−0.0019 (14)	0.0066 (13)
C66	0.0406 (16)	0.0336 (15)	0.0365 (16)	0.0103 (13)	−0.0018 (13)	0.0118 (12)
C67	0.0299 (13)	0.0339 (14)	0.0480 (16)	0.0131 (11)	0.0130 (12)	0.0131 (12)
C68	0.0341 (13)	0.0370 (14)	0.0414 (15)	0.0152 (11)	0.0162 (11)	0.0156 (12)
Cl10	0.0575 (6)	0.0552 (8)	0.0611 (7)	0.0172 (6)	0.0338 (5)	0.0164 (6)
Cl12	0.0575 (7)	0.1097 (14)	0.1041 (12)	−0.0068 (9)	0.0473 (8)	−0.0403 (11)
Cl11	0.0871 (11)	0.1210 (17)	0.0700 (9)	0.0097 (12)	0.0447 (9)	−0.0237 (10)
C100	0.061 (2)	0.049 (3)	0.052 (3)	0.025 (2)	0.030 (2)	0.015 (2)
Cl13	0.0575 (6)	0.0552 (8)	0.0611 (7)	0.0172 (6)	0.0338 (5)	0.0164 (6)
Cl14	0.0871 (11)	0.1210 (17)	0.0700 (9)	0.0097 (12)	0.0447 (9)	−0.0237 (10)
Cl15	0.0575 (7)	0.1097 (14)	0.1041 (12)	−0.0068 (9)	0.0473 (8)	−0.0403 (11)
C101	0.061 (2)	0.049 (3)	0.052 (3)	0.025 (2)	0.030 (2)	0.015 (2)
Cl20	0.0459 (5)	0.0426 (6)	0.0719 (8)	0.0104 (4)	0.0206 (5)	0.0031 (5)
Cl21	0.0435 (5)	0.0539 (8)	0.0706 (6)	0.0065 (5)	0.0245 (5)	0.0143 (5)
Cl22	0.0542 (5)	0.0328 (5)	0.1189 (9)	0.0025 (4)	0.0384 (5)	0.0159 (5)
C200	0.0372 (14)	0.0277 (16)	0.074 (2)	0.0081 (13)	0.0324 (14)	0.0097 (15)
Cl23	0.0459 (5)	0.0426 (6)	0.0719 (8)	0.0104 (4)	0.0206 (5)	0.0031 (5)
Cl25	0.0542 (5)	0.0328 (5)	0.1189 (9)	0.0025 (4)	0.0384 (5)	0.0159 (5)
Cl24	0.0435 (5)	0.0539 (8)	0.0706 (6)	0.0065 (5)	0.0245 (5)	0.0143 (5)
C201	0.0372 (14)	0.0277 (16)	0.074 (2)	0.0081 (13)	0.0324 (14)	0.0097 (15)
Cl30	0.0853 (7)	0.1689 (16)	0.0845 (8)	0.0361 (9)	0.0492 (6)	0.0189 (9)
Cl31	0.0553 (7)	0.1114 (10)	0.1534 (14)	0.0252 (7)	0.0255 (8)	0.0680 (9)
Cl32	0.0726 (7)	0.1074 (10)	0.0802 (9)	0.0408 (7)	0.0007 (7)	−0.0124 (7)
C300	0.0396 (17)	0.076 (3)	0.062 (2)	0.0186 (17)	0.0159 (17)	0.0119 (19)
Cl33	0.0853 (7)	0.1689 (16)	0.0845 (8)	0.0361 (9)	0.0492 (6)	0.0189 (9)
Cl35	0.0726 (7)	0.1074 (10)	0.0802 (9)	0.0408 (7)	0.0007 (7)	−0.0124 (7)
Cl34	0.0553 (7)	0.1114 (10)	0.1534 (14)	0.0252 (7)	0.0255 (8)	0.0680 (9)
C301	0.0396 (17)	0.076 (3)	0.062 (2)	0.0186 (17)	0.0159 (17)	0.0119 (19)
Cl40	0.1081 (10)	0.0834 (12)	0.0976 (11)	0.0496 (9)	0.0318 (9)	0.0140 (10)
Cl41	0.1144 (12)	0.0655 (11)	0.1072 (16)	0.0192 (10)	0.0182 (12)	0.0061 (9)
Cl42	0.1057 (11)	0.0682 (8)	0.0712 (9)	0.0244 (8)	0.0100 (8)	0.0226 (7)
C400	0.167 (7)	0.098 (5)	0.084 (6)	0.060 (5)	−0.022 (5)	0.013 (4)
Cl45	0.1057 (11)	0.0682 (8)	0.0712 (9)	0.0244 (8)	0.0100 (8)	0.0226 (7)
C401	0.167 (7)	0.098 (5)	0.084 (6)	0.060 (5)	−0.022 (5)	0.013 (4)
Cl44	0.1144 (12)	0.0655 (11)	0.1072 (16)	0.0192 (10)	0.0182 (12)	0.0061 (9)
Cl43	0.1081 (10)	0.0834 (12)	0.0976 (11)	0.0496 (9)	0.0318 (9)	0.0140 (10)

Geometric parameters (Å, º) top

Cl1—C16	1.738 (3)	N8—C63	1.427 (4)
Cl2—C14	1.740 (3)	N8—H8A	0.8600
Cl3—C31	1.742 (3)	C35—C36	1.369 (3)
Cl4—C33	1.745 (3)	C35—C44	1.438 (4)
O1—C11	1.215 (4)	C35—C52	1.505 (4)
O2—C28	1.231 (3)	C36—C37	1.413 (4)
N1—C11	1.364 (4)	C37—C38	1.359 (4)
N1—C2	1.417 (4)	C37—H37	0.9300
N1—H1A	0.8600	C38—C39	1.408 (4)
N2—C11	1.372 (4)	C38—H38	0.9300
N2—C12	1.417 (4)	C39—C44	1.425 (4)
N2—H2A	0.8600	C39—C40	1.436 (4)
N3—C28	1.354 (3)	C40—C41	1.357 (4)
N3—C19	1.422 (4)	C40—H40	0.9300
N3—H3A	0.8600	C41—C42	1.404 (5)
N4—C28	1.366 (4)	C41—H41	0.9300
N4—C29	1.409 (4)	C42—C43	1.363 (5)
N4—H4A	0.8600	C42—H42	0.9300
C1—C2	1.386 (4)	C43—C44	1.417 (4)
C1—C10	1.432 (4)	C43—H43	0.9300
C1—C18	1.496 (4)	C46—C51	1.377 (4)
C2—C3	1.413 (4)	C46—C47	1.391 (4)
C3—C4	1.368 (4)	C47—C48	1.384 (5)
C3—H3	0.9300	C47—H47	0.9300
C4—C5	1.406 (4)	C48—C49	1.374 (5)
C4—H4	0.9300	C49—C50	1.384 (5)
C5—C6	1.422 (4)	C49—H49	0.9300
C5—C10	1.425 (4)	C50—C51	1.377 (4)
C6—C7	1.350 (5)	C51—H51	0.9300
C6—H6	0.9300	C52—C53	1.390 (4)
C7—C8	1.411 (5)	C52—C61	1.418 (4)
C7—H7	0.9300	C53—C54	1.420 (4)
C8—C9	1.355 (4)	C54—C55	1.349 (4)
C8—H8	0.9300	C54—H54	0.9300
C9—C10	1.420 (4)	C55—C56	1.420 (4)
C9—H9	0.9300	C55—H55	0.9300
C12—C17	1.380 (4)	C56—C57	1.406 (4)
C12—C13	1.395 (4)	C56—C61	1.422 (4)
C13—C14	1.375 (4)	C57—C58	1.374 (5)
C13—H13	0.9300	C57—H57	0.9300
C14—C15	1.392 (4)	C58—C59	1.396 (5)
C15—C16	1.391 (4)	C58—H58	0.9300
C15—H15	0.9300	C59—C60	1.367 (4)
C16—C17	1.376 (4)	C59—H59	0.9300
C17—H17	0.9300	C60—C61	1.429 (4)
C18—C19	1.385 (3)	C60—H60	0.9300
C18—C27	1.435 (4)	C63—C64	1.382 (4)
C19—C20	1.407 (4)	C63—C68	1.400 (4)
C20—C21	1.358 (4)	C64—C65	1.388 (5)
C20—H20	0.9300	C64—H64	0.9300
C21—C22	1.409 (4)	C65—C66	1.368 (5)
C21—H21	0.9300	C66—C67	1.375 (5)
C22—C23	1.423 (4)	C66—H66	0.9300
C22—C27	1.426 (4)	C67—C68	1.396 (4)
C23—C24	1.347 (4)	C68—H68	0.9300
C23—H23	0.9300	Cl10—C100	1.729 (6)
C24—C25	1.400 (5)	Cl12—C100	1.693 (6)
C24—H24	0.9300	Cl11—C100	1.765 (6)
C25—C26	1.363 (4)	C100—H100	0.9800
C25—H25	0.9300	Cl13—C101	1.614 (9)
C26—C27	1.418 (4)	Cl14—C101	1.712 (9)
C26—H26	0.9300	Cl15—C101	1.759 (8)
C29—C30	1.386 (4)	C101—H101	0.9800
C29—C34	1.408 (4)	Cl20—C200	1.761 (6)
C30—C31	1.382 (4)	Cl21—C200	1.745 (8)
C30—H30	0.9300	Cl22—C200	1.754 (6)
C31—C32	1.383 (4)	C200—H200	0.9800
C32—C33	1.382 (5)	Cl23—C201	1.755 (10)
C32—H32	0.9300	Cl25—C201	1.747 (9)
C33—C34	1.366 (4)	Cl24—C201	1.741 (11)
C34—H34	0.9300	C201—H201	0.9800
Cl5—C48	1.737 (4)	Cl30—C300	1.724 (10)
Cl6—C50	1.730 (4)	Cl31—C300	1.742 (10)
Cl7—C65	1.738 (4)	Cl32—C300	1.736 (9)
Cl8—C67	1.744 (3)	C300—H300	0.9800
O3—C45	1.236 (3)	Cl33—C301	1.724 (11)
O4—C62	1.229 (3)	Cl35—C301	1.736 (10)
N5—C45	1.362 (3)	Cl34—C301	1.743 (11)
N5—C36	1.431 (4)	C301—H301	0.9800
N5—H5A	0.8600	Cl40—C400	1.743 (9)
N6—C45	1.369 (4)	Cl41—C400	1.691 (8)
N6—C46	1.408 (4)	Cl42—C400	1.687 (7)
N6—H6A	0.8600	C400—H400	0.9800
N7—C62	1.359 (4)	Cl45—C401	1.763 (16)
N7—C53	1.411 (3)	C401—Cl43	1.723 (15)
N7—H7A	0.8600	C401—Cl44	1.780 (15)
N8—C62	1.358 (3)	C401—H401	0.9800

C11—N1—C2	127.1 (3)	C38—C39—C44	120.2 (3)
C11—N1—H1A	116.4	C38—C39—C40	121.5 (2)
C2—N1—H1A	116.4	C44—C39—C40	118.3 (2)
C11—N2—C12	127.1 (2)	C41—C40—C39	121.0 (3)
C11—N2—H2A	116.4	C41—C40—H40	119.5
C12—N2—H2A	116.4	C39—C40—H40	119.5
C28—N3—C19	123.0 (2)	C40—C41—C42	119.9 (3)
C28—N3—H3A	118.5	C40—C41—H41	120.0
C19—N3—H3A	118.5	C42—C41—H41	120.0
C28—N4—C29	126.0 (2)	C43—C42—C41	121.6 (3)
C28—N4—H4A	117.0	C43—C42—H42	119.2
C29—N4—H4A	117.0	C41—C42—H42	119.2
C2—C1—C10	119.2 (2)	C42—C43—C44	120.2 (3)
C2—C1—C18	119.6 (2)	C42—C43—H43	119.9
C10—C1—C18	121.1 (2)	C44—C43—H43	119.9
C1—C2—C3	121.1 (3)	C43—C44—C39	119.1 (3)
C1—C2—N1	118.2 (2)	C43—C44—C35	122.6 (2)
C3—C2—N1	120.6 (2)	C39—C44—C35	118.3 (2)
C4—C3—C2	119.8 (3)	O3—C45—N5	122.8 (3)
C4—C3—H3	120.1	O3—C45—N6	123.4 (2)
C2—C3—H3	120.1	N5—C45—N6	113.8 (2)
C3—C4—C5	121.6 (3)	C51—C46—C47	119.9 (3)
C3—C4—H4	119.2	C51—C46—N6	118.8 (3)
C5—C4—H4	119.2	C47—C46—N6	121.3 (3)
C4—C5—C6	122.6 (3)	C48—C47—C46	118.4 (3)
C4—C5—C10	119.1 (3)	C48—C47—H47	120.8
C6—C5—C10	118.2 (3)	C46—C47—H47	120.8
C7—C6—C5	121.6 (3)	C49—C48—C47	122.9 (3)
C7—C6—H6	119.2	C49—C48—Cl5	118.7 (3)
C5—C6—H6	119.2	C47—C48—Cl5	118.4 (3)
C6—C7—C8	120.0 (3)	C48—C49—C50	117.0 (3)
C6—C7—H7	120.0	C48—C49—H49	121.5
C8—C7—H7	120.0	C50—C49—H49	121.5
C9—C8—C7	120.6 (3)	C51—C50—C49	121.8 (3)
C9—C8—H8	119.7	C51—C50—Cl6	119.6 (3)
C7—C8—H8	119.7	C49—C50—Cl6	118.6 (3)
C8—C9—C10	121.1 (3)	C46—C51—C50	119.9 (3)
C8—C9—H9	119.4	C46—C51—H51	120.1
C10—C9—H9	119.4	C50—C51—H51	120.1
C9—C10—C5	118.4 (3)	C53—C52—C61	119.1 (2)
C9—C10—C1	122.4 (3)	C53—C52—C35	119.4 (2)
C5—C10—C1	119.2 (3)	C61—C52—C35	121.4 (2)
O1—C11—N1	124.1 (3)	C52—C53—N7	117.5 (2)
O1—C11—N2	123.0 (3)	C52—C53—C54	120.7 (2)
N1—C11—N2	112.8 (3)	N7—C53—C54	121.6 (2)
C17—C12—C13	120.5 (3)	C55—C54—C53	119.7 (3)
C17—C12—N2	117.5 (3)	C55—C54—H54	120.2
C13—C12—N2	121.8 (3)	C53—C54—H54	120.2
C14—C13—C12	118.1 (3)	C54—C55—C56	122.3 (2)
C14—C13—H13	120.9	C54—C55—H55	118.9
C12—C13—H13	120.9	C56—C55—H55	118.9
C13—C14—C15	123.5 (3)	C57—C56—C55	122.6 (3)
C13—C14—Cl2	118.7 (2)	C57—C56—C61	119.6 (3)
C15—C14—Cl2	117.8 (2)	C55—C56—C61	117.8 (2)
C14—C15—C16	116.1 (3)	C58—C57—C56	121.1 (3)
C14—C15—H15	121.9	C58—C57—H57	119.5
C16—C15—H15	121.9	C56—C57—H57	119.5
C17—C16—C15	122.4 (3)	C57—C58—C59	119.4 (3)
C17—C16—Cl1	119.5 (2)	C57—C58—H58	120.3
C15—C16—Cl1	118.1 (2)	C59—C58—H58	120.3
C16—C17—C12	119.4 (3)	C60—C59—C58	121.6 (3)
C16—C17—H17	120.3	C60—C59—H59	119.2
C12—C17—H17	120.3	C58—C59—H59	119.2
C19—C18—C27	118.6 (2)	C59—C60—C61	120.2 (3)
C19—C18—C1	120.5 (2)	C59—C60—H60	119.9
C27—C18—C1	120.7 (2)	C61—C60—H60	119.9
C18—C19—C20	121.7 (3)	C52—C61—C56	120.2 (2)
C18—C19—N3	119.2 (2)	C52—C61—C60	121.8 (2)
C20—C19—N3	119.1 (2)	C56—C61—C60	118.0 (2)
C21—C20—C19	119.9 (2)	O4—C62—N8	123.2 (2)
C21—C20—H20	120.0	O4—C62—N7	123.7 (2)
C19—C20—H20	120.0	N8—C62—N7	113.1 (2)
C20—C21—C22	121.4 (3)	C64—C63—C68	120.9 (3)
C20—C21—H21	119.3	C64—C63—N8	119.9 (3)
C22—C21—H21	119.3	C68—C63—N8	119.2 (3)
C21—C22—C23	122.1 (3)	C63—C64—C65	118.8 (3)
C21—C22—C27	119.1 (3)	C63—C64—H64	120.6
C23—C22—C27	118.8 (2)	C65—C64—H64	120.6
C24—C23—C22	120.9 (3)	C66—C65—C64	122.3 (3)
C24—C23—H23	119.5	C66—C65—Cl7	119.0 (3)
C22—C23—H23	119.5	C64—C65—Cl7	118.7 (3)
C23—C24—C25	120.4 (3)	C65—C66—C67	118.0 (3)
C23—C24—H24	119.8	C65—C66—H66	121.0
C25—C24—H24	119.8	C67—C66—H66	121.0
C26—C25—C24	121.1 (3)	C66—C67—C68	122.6 (3)
C26—C25—H25	119.5	C66—C67—Cl8	119.6 (2)
C24—C25—H25	119.5	C68—C67—Cl8	117.8 (3)
C25—C26—C27	120.3 (3)	C67—C68—C63	117.5 (3)
C25—C26—H26	119.8	C67—C68—H68	121.3
C27—C26—H26	119.8	C63—C68—H68	121.3
C26—C27—C22	118.5 (3)	Cl12—C100—Cl10	117.4 (3)
C26—C27—C18	122.3 (3)	Cl12—C100—Cl11	112.0 (4)
C22—C27—C18	119.2 (2)	Cl10—C100—Cl11	112.6 (3)
O2—C28—N3	123.1 (2)	Cl12—C100—H100	104.4
O2—C28—N4	123.1 (2)	Cl10—C100—H100	104.4
N3—C28—N4	113.8 (2)	Cl11—C100—H100	104.4
C30—C29—C34	120.1 (3)	Cl13—C101—Cl14	121.0 (5)
C30—C29—N4	122.7 (2)	Cl13—C101—Cl15	113.7 (5)
C34—C29—N4	117.3 (2)	Cl14—C101—Cl15	111.0 (5)
C31—C30—C29	118.3 (3)	Cl13—C101—H101	102.8
C31—C30—H30	120.8	Cl14—C101—H101	102.8
C29—C30—H30	120.8	Cl15—C101—H101	102.8
C30—C31—C32	123.3 (3)	Cl21—C200—Cl22	112.0 (4)
C30—C31—Cl3	117.3 (2)	Cl21—C200—Cl20	109.4 (4)
C32—C31—Cl3	119.4 (2)	Cl22—C200—Cl20	111.8 (4)
C33—C32—C31	116.3 (3)	Cl21—C200—H200	107.8
C33—C32—H32	121.9	Cl22—C200—H200	107.8
C31—C32—H32	121.9	Cl20—C200—H200	107.8
C34—C33—C32	123.4 (3)	Cl24—C201—Cl25	109.4 (5)
C34—C33—Cl4	118.4 (2)	Cl24—C201—Cl23	111.8 (6)
C32—C33—Cl4	118.3 (2)	Cl25—C201—Cl23	109.6 (6)
C33—C34—C29	118.5 (3)	Cl24—C201—H201	108.6
C33—C34—H34	120.7	Cl25—C201—H201	108.6
C29—C34—H34	120.7	Cl23—C201—H201	108.6
C45—N5—C36	120.5 (2)	Cl30—C300—Cl32	111.5 (5)
C45—N5—H5A	119.7	Cl30—C300—Cl31	110.9 (6)
C36—N5—H5A	119.7	Cl32—C300—Cl31	110.4 (5)
C45—N6—C46	125.3 (2)	Cl30—C300—H300	108.0
C45—N6—H6A	117.3	Cl32—C300—H300	108.0
C46—N6—H6A	117.3	Cl31—C300—H300	108.0
C62—N7—C53	127.2 (2)	Cl33—C301—Cl35	112.2 (6)
C62—N7—H7A	116.4	Cl33—C301—Cl34	110.1 (7)
C53—N7—H7A	116.4	Cl35—C301—Cl34	109.8 (6)
C62—N8—C63	122.9 (2)	Cl33—C301—H301	108.2
C62—N8—H8A	118.5	Cl35—C301—H301	108.2
C63—N8—H8A	118.5	Cl34—C301—H301	108.2
C36—C35—C44	119.5 (2)	Cl42—C400—Cl41	116.4 (5)
C36—C35—C52	121.7 (2)	Cl42—C400—Cl40	112.7 (5)
C44—C35—C52	118.8 (2)	Cl41—C400—Cl40	113.6 (5)
C35—C36—C37	121.2 (3)	Cl42—C400—H400	104.1
C35—C36—N5	120.4 (2)	Cl41—C400—H400	104.1
C37—C36—N5	118.3 (2)	Cl40—C400—H400	104.1
C38—C37—C36	120.6 (2)	Cl43—C401—Cl45	113.6 (11)
C38—C37—H37	119.7	Cl43—C401—Cl44	103.4 (9)
C36—C37—H37	119.7	Cl45—C401—Cl44	114.7 (11)
C37—C38—C39	120.2 (2)	Cl43—C401—H401	108.3
C37—C38—H38	119.9	Cl45—C401—H401	108.3
C39—C38—H38	119.9	Cl44—C401—H401	108.3

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C56–C61 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4ⁱ	0.86	2.16	2.897 (3)	144
N4—H4A···O4ⁱ	0.86	2.05	2.821 (3)	149
N5—H5A···O2	0.86	2.11	2.821 (3)	139
N6—H6A···O2	0.86	2.17	2.947 (3)	150
N7—H7A···O3	0.86	2.36	2.955 (3)	126
N8—H8A···O3	0.86	2.26	3.030 (3)	149
C3—H3···O1	0.93	2.44	2.937 (3)	113
C13—H13···O1	0.93	2.47	2.943 (3)	112
C30—H30···O2	0.93	2.38	2.864 (3)	113
C38—H38···O1ⁱⁱ	0.93	2.41	3.304 (4)	162
C47—H47···O3	0.93	2.50	2.911 (4)	107
C54—H54···O4	0.93	2.32	2.893 (3)	120
C200—H200···O1ⁱⁱ	0.98	2.15	3.035 (7)	149
C300—H300···O3	0.98	2.52	3.315 (9)	138
N2—H2A···Cg1	0.86	2.59	3.300 (3)	141

Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₃₄H₂₂Cl₄N₄O₂·2CHCl₃
M_r	899.09
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	11.879 (2), 12.445 (3), 15.039 (3)
α, β, γ (°)	96.71 (3), 110.90 (3), 103.98 (3)
V (Å³)	1964.4 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.4 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART 1000 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20566, 16629, 13656
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.125, 1.03
No. of reflections	16629
No. of parameters	993
No. of restraints	51
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.58
Absolute structure	Flack (1983), 7535 Friedel pairs
Absolute structure parameter	−0.01 (4)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C56–C61 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4ⁱ	0.86	2.16	2.897 (3)	144
N4—H4A···O4ⁱ	0.86	2.05	2.821 (3)	149
N5—H5A···O2	0.86	2.11	2.821 (3)	139
N6—H6A···O2	0.86	2.17	2.947 (3)	150
N7—H7A···O3	0.86	2.36	2.955 (3)	126
N8—H8A···O3	0.86	2.26	3.030 (3)	149
C38—H38···O1ⁱⁱ	0.93	2.41	3.304 (4)	162
C54—H54···O4	0.93	2.32	2.893 (3)	120
C200—H200···O1ⁱⁱ	0.98	2.15	3.035 (7)	149
C300—H300···O3	0.98	2.52	3.315 (9)	138
N2—H2A···Cg1	0.86	2.59	3.300 (3)	141

Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.

Acknowledgements

We gratefully acknowledge financial support from the Ministry of Education, Youth and Sports of the Czech Republic (grant Nos. 6046137301 and 6046137302) and from the project Praemium Academiae of the Academy of Sciences of the Czech Republic..

References

Brandenburg, K. & Putz, H. (2005). DIAMOND Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fleming, E. M., McCabe, T. & Connon, S. J. (2006). Tetrahedron Lett. 47, 7037–7042. Web of Science CSD CrossRef CAS Google Scholar
Harada, S., Toudou, N., Hiraoka, S. & Nishida, A. (2009). Tetrahedron Lett. 50, 5652–5655. Web of Science CrossRef CAS Google Scholar
Liu, X.-G., Jianga, J.-J. & Shi, M. (2007). Tetrahedron Asymmetry, 18, 2773–2781. Web of Science CrossRef CAS Google Scholar
Pu, L. (1998). Chem. Rev. 98, 2405–2494. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, M. & Liu, X.-G. (2008). Org. Lett. 10, 1043–1046. Web of Science CrossRef PubMed CAS Google Scholar
Sklar, N., Senko, M. E. & Post, B. (1961). Acta Cryst. 14, 716–720. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Stibor, I., Holakovský, R., Mustafina, A. R. & Lhoták, P. (2004). Collect. Czech. Chem. Commun. 69, 365–383. Web of Science CSD CrossRef CAS Google Scholar
Takemoto, Y. (2005). Org. Biomol. Chem. 3, 4299–4306. Web of Science CrossRef PubMed CAS Google Scholar
Telfer, S. G. & Kuroda, R. (2003). Coord. Chem. Rev. 242, 33–46. Web of Science CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages o384-o385

doi:10.1107/S1600536810052657

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(R)-2,2′-Bis[N′-(3,5-di­chloro­phen­yl)ureido]-1,1′-bi­naphthalene chloro­form disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(R)-2,2′-Bis[N′-(3,5-dichlorophenyl)ureido]-1,1′-binaphthalene chloroform disolvate