6,6′-Diamino-1,1′,3,3′-tetra­methyl-5,5′-(4-chloro­benzyl­idene)bis­[pyrimidine-2,4(1H,3H)-dione]

Das, S.; Saikia, B.K.; Das, B.; Saikia, L.; Thakur, A.J.

doi:10.1107/S1600536809035818

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages o2416-o2417

doi:10.1107/S1600536809035818

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6,6′-Diamino-1,1′,3,3′-tetramethyl-5,5′-(4-chlorobenzylidene)bis[pyrimidine-2,4(1H,3H)-dione]

Subrata Das,^a Binoy K. Saikia,^a Babulal Das,^b Lakhinath Saikia ^a and Ashim J. Thakur ^a ^*

^aDepartment of Chemical Sciences, Tezpur University, Tezpur 784 028, India, and ^bDepartment of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India
^*Correspondence e-mail: ashim@tezu.ernet.in

(Received 24 August 2009; accepted 4 September 2009; online 9 September 2009)

The title compound, C₁₉H₂₁ClN₆O₄, is a 1:2 adduct of p-chlorobenzaldehyde and uracil. It crystallizes with two molecules in the asymmetric unit. The two uracil units in the same molecule are connected by a pair of strong N—H⋯O hydrogen bonds. The packing is stabilized by N—H⋯O, C—H⋯O and C—H⋯N interactions.

Related literature

For the biological activity and medicinal applications of heterocyclic compounds, especially pyrimidine derivatives, see: Zheng et al. (2007 ); Jain et al. (2006 ). The title compound was synthesized from 6-amino- 1,3-dimethylpyrimidine-2,4(1H, 3H)-dione, which is an important building block, see: Blicke & Godt (1954 ); Das et al. (2008 ).

Experimental

Crystal data

C₁₉H₂₁ClN₆O₄
M_r = 432.87
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.5365 (3) Å
b = 14.5935 (4) Å
c = 23.2102 (6) Å
V = 3907.62 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.40 × 0.28 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
53787 measured reflections
9742 independent reflections
6901 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.166
S = 1.06
9742 reflections
549 parameters
H-atom parameters constrained
Δρ_max = 1.27 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ), 4345 Friedel pairs
Flack parameter: 0.15 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O4	0.86	2.13	2.966 (4)	164
N3—H3B⋯O1ⁱ	0.86	2.26	3.059 (3)	154
N6—H6A⋯O6ⁱ	0.86	2.29	3.041 (3)	146
N6—H6B⋯O1	0.86	1.93	2.761 (3)	161
N9—H9A⋯O4ⁱⁱ	0.86	2.51	3.243 (4)	144
N9—H9B⋯O8	0.86	1.98	2.799 (3)	159
N12—H12A⋯O6	0.86	2.09	2.924 (3)	163
N12—H12B⋯O8ⁱⁱ	0.86	2.32	3.106 (3)	153
C1—H1⋯O4	0.98	2.22	2.794 (4)	116
C1—H1⋯N3	0.98	2.41	2.887 (4)	109
C12—H12C⋯O1ⁱ	0.96	2.45	3.164 (4)	131
C12—H12D⋯O2	0.96	2.27	2.708 (4)	107
C12—H12D⋯O5ⁱⁱⁱ	0.96	2.60	3.322 (4)	133
C13—H13A⋯O2	0.96	2.36	2.713 (4)	101
C18—H18B⋯O4	0.96	2.24	2.673 (6)	106
C19—H19B⋯O3	0.96	2.23	2.650 (5)	105
C20—H20⋯O6	0.98	2.23	2.807 (4)	116
C20—H20⋯N12	0.98	2.41	2.876 (4)	108
C31—H31B⋯O5	0.96	2.27	2.715 (5)	108
C32—H32A⋯O5	0.96	2.33	2.711 (5)	103
C37—H37A⋯O8ⁱⁱ	0.96	2.57	3.208 (4)	124
C37—H37C⋯O7	0.96	2.28	2.707 (4)	106
C38—H38B⋯O8	0.96	2.27	2.699 (4)	106
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809035818/bt5045sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809035818/bt5045Isup2.hkl

checkCIF report

Comment top

Heterocyclic compounds, especially six-membered pyrimidine ring and their derivatives have occupied an important place among organic compounds owing to their various biological signifiances (Zheng et al., 2007). They have been explored for the development of various pharmaceutically important compounds because of their medicinal values (Jain et al., 2006). They also form the basic structural fragment of many alkaloids and pharmacologically active compounds. As part of our ongoing programme on bioactive pyrimidine molecules, we have synthesized a new pyrimidine compound starting from an important building block namely 6-Amino- 1,3-dimethylpyrimidine-2,4(1H, 3H)-dione (Blicke & Godt, 1954; Das et al., 2008). The title compound crystallizes with two molecules in the asymmetric unit. The two uracil moieties in the same molecule are connected by a pair of strong N—H···O hydrogen bonds. The packing is stabilized by N—H···.O, C—H···.O and C—H···.N interactions.

Related literature top

For the biological activity and medicinal applications of heterocyclic compounds, especially pyrimidine derivatives, see: Zheng et al. (2007); Jain et al. (2006). The title compound was synthesized from 6-amino- 1,3-dimethylpyrimidine-2,4(1H, 3H)-dione, which is an important building block, see: Blicke & Godt (1954); Das et al. (2008)

Experimental top

Distilled water was added in excess to 6-Amino-1,3-dimethylpyrimidine-2,4(1H,3H) -dione (2 mmol) in order to dissolve it completely in a stirring condition. Then, p-chlorobenzaldehyde was added until a precipitate appeared. After 1 hr of stirring the product was filtered and purified by column chromatography. The product was recrystallized by using distilled ethanol, yielding suitable crystals for data collection.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. An ORTEP view of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

6,6'-Diamino-1,1',3,3'-tetramethyl-5,5'-(4-chlorobenzylidene)bis[pyrimidine- 2,4(1H,3H)-dione] top

Crystal data top

C₁₉H₂₁ClN₆O₄	D_x = 1.472 Mg m⁻³
M_r = 432.87	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 9985 reflections
a = 11.5365 (3) Å	θ = 2.2–25.7°
b = 14.5935 (4) Å	µ = 0.24 mm⁻¹
c = 23.2102 (6) Å	T = 293 K
V = 3907.62 (18) Å³	Blocks, colorless
Z = 8	0.40 × 0.28 × 0.16 mm
F(000) = 1808

Data collection top

Bruker SMART CCD area-detector diffractometer	6901 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.038
Graphite monochromator	θ_max = 28.4°, θ_min = 1.7°
ϕ and ω scans	h = −15→15
53787 measured reflections	k = −19→19
9742 independent reflections	l = −30→30

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)] = 0.056	H-atom parameters constrained
wR(F²) = 0.166	w = 1/[σ²(F_o²) + (0.09P)² + 0.7964P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
9742 reflections	Δρ_max = 1.27 e Å⁻³
549 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 4345 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.15 (8)

Crystal data top

C₁₉H₂₁ClN₆O₄	V = 3907.62 (18) Å³
M_r = 432.87	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.5365 (3) Å	µ = 0.24 mm⁻¹
b = 14.5935 (4) Å	T = 293 K
c = 23.2102 (6) Å	0.40 × 0.28 × 0.16 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	6901 reflections with I > 2σ(I)
53787 measured reflections	R_int = 0.038
9742 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	H-atom parameters constrained
wR(F²) = 0.166	Δρ_max = 1.27 e Å⁻³
S = 1.06	Δρ_min = −0.28 e Å⁻³
9742 reflections	Absolute structure: Flack (1983), 4345 Friedel pairs
549 parameters	Absolute structure parameter: 0.15 (8)
0 restraints

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1	0.87268 (9)	0.84719 (7)	0.14783 (4)	0.0691 (3)
Cl2	0.62621 (10)	0.67886 (8)	0.36362 (6)	0.0842 (4)
O8	1.06232 (19)	0.88990 (14)	0.27567 (9)	0.0449 (5)
N10	0.9975 (2)	1.12225 (16)	0.18849 (10)	0.0409 (6)
C27	0.9774 (3)	1.0599 (2)	0.38507 (12)	0.0388 (6)
O1	0.43437 (19)	0.63236 (14)	0.23040 (9)	0.0462 (5)
N11	1.0865 (2)	0.97903 (16)	0.19627 (10)	0.0384 (5)
N6	0.3816 (2)	0.59997 (17)	0.11616 (11)	0.0452 (6)
H6A	0.3264	0.6301	0.1000	0.054*
H6B	0.4096	0.6184	0.1485	0.054*
N2	0.4159 (2)	0.53819 (17)	0.30849 (10)	0.0392 (6)
C11	0.4596 (3)	0.55679 (19)	0.25331 (12)	0.0362 (6)
C14	0.5145 (3)	0.4746 (2)	0.11458 (12)	0.0403 (7)
C36	1.0386 (2)	0.96383 (19)	0.25117 (12)	0.0351 (6)
C3	0.6561 (3)	0.6419 (2)	0.11131 (12)	0.0402 (6)
H3	0.6126	0.6229	0.0798	0.048*
N1	0.5063 (2)	0.39511 (16)	0.31134 (10)	0.0386 (6)
C10	0.4440 (3)	0.4624 (2)	0.34031 (13)	0.0396 (6)
O7	1.0992 (2)	1.06161 (18)	0.11334 (10)	0.0649 (7)
O6	0.8555 (2)	1.19062 (15)	0.38902 (10)	0.0514 (5)
C9	0.5423 (2)	0.40516 (19)	0.25483 (11)	0.0338 (6)
C1	0.5849 (3)	0.50156 (19)	0.16763 (12)	0.0371 (6)
H1	0.6471	0.4558	0.1680	0.044*
C30	0.9395 (3)	1.1447 (2)	0.40763 (13)	0.0421 (7)
N9	1.1133 (2)	0.93617 (19)	0.38994 (12)	0.0477 (6)
H9A	1.1693	0.9094	0.4076	0.057*
H9B	1.0852	0.9126	0.3590	0.057*
C20	0.9093 (2)	1.02501 (19)	0.33366 (12)	0.0353 (6)
H20	0.8455	1.0691	0.3310	0.042*
C34	0.9553 (3)	1.11502 (19)	0.24430 (12)	0.0355 (6)
O4	0.6321 (3)	0.34234 (19)	0.10500 (11)	0.0808 (10)
C33	0.9683 (3)	1.03421 (19)	0.27454 (12)	0.0345 (6)
N3	0.5937 (2)	0.33165 (16)	0.23116 (11)	0.0435 (6)
H3A	0.6195	0.3343	0.1964	0.052*
H3B	0.6009	0.2819	0.2507	0.052*
N5	0.3759 (2)	0.49787 (19)	0.03907 (11)	0.0450 (6)
O2	0.4133 (3)	0.45193 (18)	0.38953 (10)	0.0665 (7)
C17	0.4243 (3)	0.5239 (2)	0.09087 (13)	0.0398 (7)
N12	0.9021 (2)	1.18920 (17)	0.26519 (11)	0.0446 (6)
H12A	0.8735	1.1884	0.2994	0.054*
H12B	0.8965	1.2378	0.2444	0.054*
C8	0.5272 (3)	0.48760 (19)	0.22656 (12)	0.0357 (6)
C24	0.7074 (3)	0.7778 (2)	0.35625 (15)	0.0497 (8)
C21	0.8455 (2)	0.93356 (19)	0.34220 (12)	0.0347 (6)
N8	0.9983 (2)	1.1785 (2)	0.45592 (11)	0.0516 (7)
C2	0.6515 (2)	0.59179 (19)	0.16235 (12)	0.0369 (6)
N7	1.1188 (2)	1.0487 (2)	0.46059 (11)	0.0511 (7)
C35	1.0637 (3)	1.0546 (2)	0.16289 (13)	0.0437 (7)
C4	0.7240 (3)	0.7190 (2)	0.10674 (14)	0.0450 (7)
H4	0.7253	0.7519	0.0724	0.054*
O5	1.1412 (2)	1.1681 (2)	0.52252 (11)	0.0755 (8)
C7	0.7218 (3)	0.6211 (2)	0.20748 (13)	0.0447 (7)
H7	0.7219	0.5882	0.2418	0.054*
C22	0.7752 (3)	0.9018 (2)	0.29750 (13)	0.0407 (7)
H22	0.7749	0.9329	0.2625	0.049*
C26	0.8422 (3)	0.8873 (2)	0.39395 (13)	0.0405 (7)
H26	0.8865	0.9085	0.4247	0.049*
C12	0.5385 (3)	0.3124 (2)	0.34431 (14)	0.0515 (8)
H12C	0.4977	0.2604	0.3291	0.077*
H12D	0.5181	0.3207	0.3841	0.077*
H12E	0.6204	0.3023	0.3412	0.077*
O3	0.3531 (3)	0.3928 (2)	−0.03150 (11)	0.0852 (9)
C23	0.7055 (3)	0.8249 (2)	0.30412 (14)	0.0471 (7)
H23	0.6583	0.8052	0.2741	0.057*
C5	0.7897 (3)	0.7477 (2)	0.15242 (14)	0.0436 (7)
C15	0.5501 (4)	0.3921 (3)	0.08698 (13)	0.0562 (9)
C6	0.7909 (3)	0.6971 (2)	0.20284 (14)	0.0488 (8)
H6	0.8382	0.7146	0.2334	0.059*
C16	0.4053 (4)	0.4160 (3)	0.01292 (15)	0.0588 (10)
C25	0.7737 (3)	0.8091 (2)	0.40128 (15)	0.0487 (8)
H25	0.7731	0.7785	0.4364	0.058*
N4	0.4919 (3)	0.3658 (2)	0.03778 (11)	0.0617 (9)
C29	1.0896 (3)	1.1343 (3)	0.48273 (14)	0.0561 (9)
C28	1.0693 (3)	1.0151 (2)	0.41075 (13)	0.0432 (7)
C37	0.9705 (4)	1.2031 (2)	0.15333 (14)	0.0581 (9)
H37A	1.0169	1.2539	0.1659	0.087*
H37B	0.8899	1.2181	0.1575	0.087*
H37C	0.9870	1.1901	0.1136	0.087*
C13	0.3377 (3)	0.6053 (2)	0.33519 (14)	0.0520 (8)
H13A	0.2920	0.5757	0.3643	0.078*
H13B	0.2875	0.6307	0.3063	0.078*
H13C	0.3825	0.6535	0.3524	0.078*
C38	1.1673 (3)	0.9112 (2)	0.17263 (15)	0.0513 (8)
H38A	1.1296	0.8771	0.1426	0.077*
H38B	1.1914	0.8702	0.2027	0.077*
H38C	1.2339	0.9420	0.1571	0.077*
C19	0.2869 (3)	0.5538 (3)	0.00979 (15)	0.0596 (9)
H19A	0.2140	0.5468	0.0292	0.089*
H19B	0.2792	0.5340	−0.0295	0.089*
H19C	0.3096	0.6171	0.0106	0.089*
C31	1.2062 (4)	0.9963 (3)	0.49141 (17)	0.0708 (12)
H31A	1.1736	0.9392	0.5039	0.106*
H31B	1.2320	1.0305	0.5243	0.106*
H31C	1.2708	0.9847	0.4664	0.106*
C32	0.9631 (4)	1.2684 (3)	0.47975 (17)	0.0706 (12)
H32A	0.9899	1.2736	0.5188	0.106*
H32B	0.8801	1.2733	0.4790	0.106*
H32C	0.9963	1.3166	0.4569	0.106*
C18	0.5258 (6)	0.2797 (3)	0.01056 (19)	0.109 (2)
H18A	0.4577	0.2460	−0.0002	0.163*
H18B	0.5710	0.2441	0.0371	0.163*
H18C	0.5712	0.2924	−0.0232	0.163*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0614 (6)	0.0759 (6)	0.0700 (6)	−0.0308 (5)	0.0047 (5)	−0.0041 (5)
Cl2	0.0732 (7)	0.0615 (6)	0.1179 (9)	−0.0344 (5)	−0.0091 (6)	0.0144 (6)
O8	0.0568 (14)	0.0364 (11)	0.0415 (11)	0.0065 (10)	0.0041 (10)	−0.0002 (9)
N10	0.0547 (15)	0.0348 (12)	0.0331 (12)	−0.0055 (11)	0.0044 (11)	0.0006 (10)
C27	0.0420 (16)	0.0391 (15)	0.0353 (14)	−0.0089 (13)	0.0064 (13)	−0.0026 (12)
O1	0.0599 (14)	0.0363 (11)	0.0422 (11)	0.0113 (10)	0.0016 (10)	0.0011 (9)
N11	0.0389 (13)	0.0387 (13)	0.0374 (13)	−0.0029 (10)	0.0045 (11)	−0.0033 (10)
N6	0.0435 (14)	0.0437 (14)	0.0484 (14)	0.0042 (11)	−0.0080 (12)	−0.0082 (12)
N2	0.0410 (13)	0.0387 (13)	0.0380 (13)	0.0004 (11)	0.0074 (11)	−0.0024 (10)
C11	0.0424 (16)	0.0326 (14)	0.0334 (14)	−0.0011 (12)	0.0020 (13)	0.0027 (11)
C14	0.0546 (18)	0.0343 (14)	0.0321 (14)	0.0010 (13)	0.0075 (13)	−0.0004 (11)
C36	0.0352 (15)	0.0343 (14)	0.0357 (14)	−0.0028 (12)	−0.0006 (12)	−0.0055 (11)
C3	0.0405 (16)	0.0462 (16)	0.0340 (14)	−0.0016 (13)	−0.0024 (13)	0.0045 (13)
N1	0.0491 (15)	0.0311 (12)	0.0357 (12)	−0.0046 (10)	0.0015 (11)	0.0034 (10)
C10	0.0431 (16)	0.0417 (16)	0.0339 (15)	−0.0028 (13)	0.0063 (13)	0.0013 (12)
O7	0.0772 (17)	0.0715 (17)	0.0459 (13)	0.0076 (14)	0.0232 (13)	0.0079 (12)
O6	0.0567 (14)	0.0451 (12)	0.0525 (13)	−0.0015 (11)	0.0085 (11)	−0.0105 (10)
C9	0.0357 (15)	0.0337 (14)	0.0320 (14)	−0.0027 (11)	−0.0005 (12)	0.0007 (11)
C1	0.0434 (16)	0.0329 (14)	0.0349 (14)	0.0083 (12)	0.0024 (12)	0.0035 (11)
C30	0.0435 (17)	0.0425 (16)	0.0404 (16)	−0.0154 (14)	0.0115 (13)	−0.0097 (13)
N9	0.0459 (15)	0.0518 (15)	0.0455 (14)	−0.0006 (12)	−0.0062 (12)	−0.0039 (12)
C20	0.0351 (14)	0.0348 (14)	0.0360 (14)	−0.0038 (11)	0.0029 (12)	−0.0021 (11)
C34	0.0368 (15)	0.0326 (14)	0.0371 (14)	−0.0045 (11)	−0.0003 (12)	−0.0028 (11)
O4	0.137 (3)	0.0604 (16)	0.0452 (13)	0.0466 (18)	−0.0001 (16)	−0.0088 (12)
C33	0.0406 (16)	0.0334 (14)	0.0296 (13)	−0.0047 (12)	0.0039 (12)	−0.0051 (11)
N3	0.0613 (16)	0.0313 (12)	0.0380 (13)	0.0064 (12)	0.0050 (12)	0.0043 (10)
N5	0.0443 (15)	0.0530 (15)	0.0377 (13)	−0.0016 (12)	0.0070 (11)	−0.0035 (12)
O2	0.094 (2)	0.0638 (16)	0.0421 (13)	0.0103 (14)	0.0229 (14)	0.0082 (12)
C17	0.0417 (16)	0.0396 (15)	0.0381 (15)	−0.0061 (13)	0.0102 (13)	0.0025 (12)
N12	0.0573 (16)	0.0337 (12)	0.0430 (13)	0.0029 (12)	0.0063 (12)	0.0026 (11)
C8	0.0404 (16)	0.0322 (14)	0.0347 (14)	0.0013 (12)	0.0014 (12)	0.0024 (11)
C24	0.0365 (16)	0.0418 (16)	0.071 (2)	−0.0085 (13)	0.0025 (16)	0.0015 (16)
C21	0.0331 (14)	0.0334 (14)	0.0375 (14)	−0.0017 (11)	0.0027 (12)	−0.0010 (11)
N8	0.0562 (17)	0.0572 (17)	0.0415 (14)	−0.0141 (14)	0.0102 (13)	−0.0173 (13)
C2	0.0369 (15)	0.0382 (15)	0.0355 (14)	0.0087 (12)	0.0068 (12)	0.0019 (11)
N7	0.0448 (15)	0.0738 (19)	0.0347 (13)	−0.0116 (14)	−0.0010 (12)	−0.0082 (13)
C35	0.0463 (17)	0.0463 (17)	0.0386 (16)	−0.0049 (13)	0.0045 (14)	−0.0058 (13)
C4	0.0391 (16)	0.0514 (18)	0.0446 (16)	−0.0070 (14)	0.0058 (14)	0.0097 (14)
O5	0.0670 (17)	0.109 (2)	0.0505 (14)	−0.0212 (17)	−0.0030 (13)	−0.0290 (15)
C7	0.0473 (18)	0.0517 (18)	0.0351 (15)	0.0068 (15)	−0.0039 (13)	0.0084 (14)
C22	0.0403 (16)	0.0426 (16)	0.0393 (15)	−0.0019 (13)	−0.0062 (13)	−0.0013 (13)
C26	0.0352 (15)	0.0451 (16)	0.0411 (15)	−0.0064 (13)	−0.0025 (13)	0.0019 (13)
C12	0.077 (2)	0.0342 (15)	0.0434 (16)	0.0047 (15)	0.0043 (17)	0.0115 (13)
O3	0.111 (2)	0.097 (2)	0.0483 (15)	0.003 (2)	−0.0025 (16)	−0.0330 (15)
C23	0.0373 (16)	0.0462 (18)	0.0578 (19)	−0.0046 (14)	−0.0075 (14)	−0.0057 (15)
C5	0.0323 (15)	0.0494 (17)	0.0492 (17)	−0.0044 (13)	0.0040 (14)	−0.0009 (14)
C15	0.083 (3)	0.052 (2)	0.0332 (16)	0.0119 (19)	0.0099 (17)	0.0019 (14)
C6	0.0408 (17)	0.058 (2)	0.0476 (18)	0.0013 (15)	−0.0088 (14)	−0.0032 (15)
C16	0.069 (2)	0.069 (2)	0.0384 (17)	−0.009 (2)	0.0109 (17)	−0.0094 (17)
C25	0.0457 (17)	0.0458 (18)	0.0546 (19)	−0.0040 (14)	−0.0005 (15)	0.0139 (15)
N4	0.099 (3)	0.0522 (17)	0.0336 (13)	0.0071 (17)	0.0081 (15)	−0.0124 (13)
C29	0.059 (2)	0.074 (2)	0.0352 (16)	−0.0236 (19)	0.0099 (16)	−0.0163 (17)
C28	0.0427 (17)	0.0527 (19)	0.0341 (15)	−0.0165 (14)	0.0045 (13)	−0.0025 (13)
C37	0.089 (3)	0.0460 (19)	0.0389 (16)	−0.0015 (18)	0.0128 (18)	0.0104 (14)
C13	0.0527 (19)	0.0535 (19)	0.0497 (18)	0.0154 (16)	0.0073 (16)	−0.0052 (15)
C38	0.0471 (18)	0.054 (2)	0.0532 (19)	0.0068 (15)	0.0106 (16)	−0.0085 (15)
C19	0.052 (2)	0.084 (3)	0.0426 (17)	−0.0011 (19)	−0.0005 (16)	0.0002 (18)
C31	0.064 (3)	0.093 (3)	0.055 (2)	−0.001 (2)	−0.0132 (19)	−0.010 (2)
C32	0.084 (3)	0.065 (2)	0.063 (2)	−0.016 (2)	0.021 (2)	−0.035 (2)
C18	0.193 (6)	0.074 (3)	0.059 (3)	0.043 (4)	0.000 (3)	−0.032 (2)

Geometric parameters (Å, º) top

Cl1—C5	1.743 (3)	N12—H12A	0.8600
Cl2—C24	1.730 (3)	N12—H12B	0.8600
O8—C36	1.250 (3)	C24—C25	1.373 (5)
N10—C35	1.383 (4)	C24—C23	1.392 (5)
N10—C34	1.388 (4)	C21—C26	1.379 (4)
N10—C37	1.468 (4)	C21—C22	1.396 (4)
C27—C28	1.381 (5)	N8—C29	1.383 (5)
C27—C30	1.414 (4)	N8—C32	1.481 (4)
C27—C20	1.517 (4)	C2—C7	1.392 (4)
O1—C11	1.258 (3)	N7—C28	1.380 (4)
N11—C35	1.373 (4)	N7—C29	1.393 (5)
N11—C36	1.406 (4)	N7—C31	1.454 (5)
N11—C38	1.466 (4)	C4—C5	1.369 (4)
N6—C17	1.349 (4)	C4—H4	0.9300
N6—H6A	0.8600	O5—C29	1.204 (4)
N6—H6B	0.8600	C7—C6	1.369 (5)
N2—C10	1.369 (4)	C7—H7	0.9300
N2—C11	1.403 (4)	C22—C23	1.388 (4)
N2—C13	1.469 (4)	C22—H22	0.9300
C11—C8	1.419 (4)	C26—C25	1.397 (4)
C14—C17	1.380 (4)	C26—H26	0.9300
C14—C15	1.424 (4)	C12—H12C	0.9600
C14—C1	1.527 (4)	C12—H12D	0.9600
C36—C33	1.417 (4)	C12—H12E	0.9600
C3—C4	1.376 (4)	O3—C16	1.241 (4)
C3—C2	1.393 (4)	C23—H23	0.9300
C3—H3	0.9300	C5—C6	1.383 (4)
N1—C9	1.384 (4)	C15—N4	1.379 (5)
N1—C10	1.391 (4)	C6—H6	0.9300
N1—C12	1.477 (4)	C16—N4	1.367 (5)
C10—O2	1.206 (4)	C25—H25	0.9300
O7—C35	1.225 (4)	N4—C18	1.460 (5)
O6—C30	1.254 (4)	C37—H37A	0.9600
C9—N3	1.343 (4)	C37—H37B	0.9600
C9—C8	1.381 (4)	C37—H37C	0.9600
C1—C2	1.530 (4)	C13—H13A	0.9600
C1—C8	1.535 (4)	C13—H13B	0.9600
C1—H1	0.9800	C13—H13C	0.9600
C30—N8	1.400 (4)	C38—H38A	0.9600
N9—C28	1.347 (4)	C38—H38B	0.9600
N9—H9A	0.8600	C38—H38C	0.9600
N9—H9B	0.8600	C19—H19A	0.9600
C20—C21	1.537 (4)	C19—H19B	0.9600
C20—C33	1.538 (4)	C19—H19C	0.9600
C20—H20	0.9800	C31—H31A	0.9600
C34—N12	1.335 (4)	C31—H31B	0.9600
C34—C33	1.380 (4)	C31—H31C	0.9600
O4—C15	1.264 (5)	C32—H32A	0.9600
N3—H3A	0.8600	C32—H32B	0.9600
N3—H3B	0.8600	C32—H32C	0.9600
N5—C17	1.379 (4)	C18—H18A	0.9600
N5—C16	1.382 (5)	C18—H18B	0.9600
N5—C19	1.478 (5)	C18—H18C	0.9600

C35—N10—C34	122.7 (2)	O7—C35—N11	122.2 (3)
C35—N10—C37	116.9 (2)	O7—C35—N10	121.9 (3)
C34—N10—C37	120.4 (3)	N11—C35—N10	115.9 (2)
C28—C27—C30	119.5 (3)	C5—C4—C3	120.4 (3)
C28—C27—C20	125.3 (3)	C5—C4—H4	119.8
C30—C27—C20	115.1 (3)	C3—C4—H4	119.8
C35—N11—C36	124.2 (2)	C6—C7—C2	121.9 (3)
C35—N11—C38	116.9 (3)	C6—C7—H7	119.0
C36—N11—C38	118.8 (3)	C2—C7—H7	119.0
C17—N6—H6A	120.0	C23—C22—C21	121.5 (3)
C17—N6—H6B	120.0	C23—C22—H22	119.3
H6A—N6—H6B	120.0	C21—C22—H22	119.3
C10—N2—C11	124.4 (2)	C21—C26—C25	121.4 (3)
C10—N2—C13	117.2 (2)	C21—C26—H26	119.3
C11—N2—C13	118.5 (2)	C25—C26—H26	119.3
O1—C11—N2	118.2 (3)	N1—C12—H12C	109.5
O1—C11—C8	124.5 (3)	N1—C12—H12D	109.5
N2—C11—C8	117.3 (2)	H12C—C12—H12D	109.5
C17—C14—C15	118.6 (3)	N1—C12—H12E	109.5
C17—C14—C1	126.1 (3)	H12C—C12—H12E	109.5
C15—C14—C1	115.3 (3)	H12D—C12—H12E	109.5
O8—C36—N11	117.5 (3)	C22—C23—C24	119.1 (3)
O8—C36—C33	125.2 (3)	C22—C23—H23	120.5
N11—C36—C33	117.2 (3)	C24—C23—H23	120.5
C4—C3—C2	121.1 (3)	C4—C5—C6	119.9 (3)
C4—C3—H3	119.4	C4—C5—Cl1	120.8 (2)
C2—C3—H3	119.4	C6—C5—Cl1	119.4 (2)
C9—N1—C10	122.6 (2)	O4—C15—N4	118.6 (3)
C9—N1—C12	120.2 (3)	O4—C15—C14	123.6 (3)
C10—N1—C12	117.2 (2)	N4—C15—C14	117.9 (3)
O2—C10—N2	123.0 (3)	C7—C6—C5	119.5 (3)
O2—C10—N1	121.4 (3)	C7—C6—H6	120.2
N2—C10—N1	115.6 (2)	C5—C6—H6	120.2
N3—C9—C8	123.8 (3)	O3—C16—N4	124.0 (4)
N3—C9—N1	115.8 (2)	O3—C16—N5	118.8 (4)
C8—C9—N1	120.3 (3)	N4—C16—N5	117.2 (3)
C14—C1—C2	115.1 (2)	C24—C25—C26	119.6 (3)
C14—C1—C8	117.0 (2)	C24—C25—H25	120.2
C2—C1—C8	113.8 (2)	C26—C25—H25	120.2
C14—C1—H1	102.7	C16—N4—C15	123.8 (3)
C2—C1—H1	102.7	C16—N4—C18	118.4 (4)
C8—C1—H1	102.7	C15—N4—C18	117.9 (4)
O6—C30—N8	117.5 (3)	O5—C29—N8	122.1 (4)
O6—C30—C27	125.4 (3)	O5—C29—N7	122.1 (4)
N8—C30—C27	117.0 (3)	N8—C29—N7	115.9 (3)
C28—N9—H9A	120.0	N9—C28—N7	116.7 (3)
C28—N9—H9B	120.0	N9—C28—C27	122.6 (3)
H9A—N9—H9B	120.0	N7—C28—C27	120.7 (3)
C27—C20—C21	116.0 (2)	N10—C37—H37A	109.5
C27—C20—C33	116.3 (2)	N10—C37—H37B	109.5
C21—C20—C33	113.8 (2)	H37A—C37—H37B	109.5
C27—C20—H20	102.6	N10—C37—H37C	109.5
C21—C20—H20	102.6	H37A—C37—H37C	109.5
C33—C20—H20	102.6	H37B—C37—H37C	109.5
N12—C34—C33	123.9 (3)	N2—C13—H13A	109.5
N12—C34—N10	116.0 (2)	N2—C13—H13B	109.5
C33—C34—N10	120.1 (3)	H13A—C13—H13B	109.5
C34—C33—C36	119.1 (3)	N2—C13—H13C	109.5
C34—C33—C20	118.7 (3)	H13A—C13—H13C	109.5
C36—C33—C20	122.1 (3)	H13B—C13—H13C	109.5
C9—N3—H3A	120.0	N11—C38—H38A	109.5
C9—N3—H3B	120.0	N11—C38—H38B	109.5
H3A—N3—H3B	120.0	H38A—C38—H38B	109.5
C17—N5—C16	121.5 (3)	N11—C38—H38C	109.5
C17—N5—C19	122.0 (3)	H38A—C38—H38C	109.5
C16—N5—C19	116.5 (3)	H38B—C38—H38C	109.5
N6—C17—N5	117.3 (3)	N5—C19—H19A	109.5
N6—C17—C14	122.1 (3)	N5—C19—H19B	109.5
N5—C17—C14	120.6 (3)	H19A—C19—H19B	109.5
C34—N12—H12A	120.0	N5—C19—H19C	109.5
C34—N12—H12B	120.0	H19A—C19—H19C	109.5
H12A—N12—H12B	120.0	H19B—C19—H19C	109.5
C9—C8—C11	118.8 (3)	N7—C31—H31A	109.5
C9—C8—C1	119.0 (3)	N7—C31—H31B	109.5
C11—C8—C1	122.3 (2)	H31A—C31—H31B	109.5
C25—C24—C23	120.4 (3)	N7—C31—H31C	109.5
C25—C24—Cl2	120.3 (3)	H31A—C31—H31C	109.5
C23—C24—Cl2	119.3 (3)	H31B—C31—H31C	109.5
C26—C21—C22	117.9 (3)	N8—C32—H32A	109.5
C26—C21—C20	123.4 (3)	N8—C32—H32B	109.5
C22—C21—C20	118.1 (3)	H32A—C32—H32B	109.5
C29—N8—C30	124.4 (3)	N8—C32—H32C	109.5
C29—N8—C32	117.0 (3)	H32A—C32—H32C	109.5
C30—N8—C32	118.5 (3)	H32B—C32—H32C	109.5
C7—C2—C3	117.1 (3)	N4—C18—H18A	109.5
C7—C2—C1	119.8 (3)	N4—C18—H18B	109.5
C3—C2—C1	122.6 (3)	H18A—C18—H18B	109.5
C28—N7—C29	121.9 (3)	N4—C18—H18C	109.5
C28—N7—C31	120.8 (3)	H18A—C18—H18C	109.5
C29—N7—C31	117.2 (3)	H18B—C18—H18C	109.5

C10—N2—C11—O1	−174.5 (3)	C27—C20—C21—C22	175.6 (3)
C13—N2—C11—O1	3.5 (4)	C33—C20—C21—C22	−45.5 (4)
C10—N2—C11—C8	7.0 (4)	O6—C30—N8—C29	177.5 (3)
C13—N2—C11—C8	−175.0 (3)	C27—C30—N8—C29	−0.4 (4)
C35—N11—C36—O8	176.5 (3)	O6—C30—N8—C32	−3.7 (4)
C38—N11—C36—O8	−4.3 (4)	C27—C30—N8—C32	178.3 (3)
C35—N11—C36—C33	−4.1 (4)	C4—C3—C2—C7	−2.5 (4)
C38—N11—C36—C33	175.0 (3)	C4—C3—C2—C1	−174.9 (3)
C11—N2—C10—O2	173.3 (3)	C14—C1—C2—C7	−177.7 (3)
C13—N2—C10—O2	−4.7 (5)	C8—C1—C2—C7	43.3 (4)
C11—N2—C10—N1	−9.5 (4)	C14—C1—C2—C3	−5.4 (4)
C13—N2—C10—N1	172.4 (3)	C8—C1—C2—C3	−144.4 (3)
C9—N1—C10—O2	179.8 (3)	C36—N11—C35—O7	−173.6 (3)
C12—N1—C10—O2	−3.0 (5)	C38—N11—C35—O7	7.2 (5)
C9—N1—C10—N2	2.6 (4)	C36—N11—C35—N10	6.0 (4)
C12—N1—C10—N2	179.8 (3)	C38—N11—C35—N10	−173.2 (3)
C10—N1—C9—N3	−175.0 (3)	C34—N10—C35—O7	179.2 (3)
C12—N1—C9—N3	7.9 (4)	C37—N10—C35—O7	0.5 (5)
C10—N1—C9—C8	6.6 (4)	C34—N10—C35—N11	−0.5 (4)
C12—N1—C9—C8	−170.5 (3)	C37—N10—C35—N11	−179.1 (3)
C17—C14—C1—C2	−61.2 (4)	C2—C3—C4—C5	0.7 (5)
C15—C14—C1—C2	116.5 (3)	C3—C2—C7—C6	1.5 (4)
C17—C14—C1—C8	76.4 (4)	C1—C2—C7—C6	174.2 (3)
C15—C14—C1—C8	−105.8 (3)	C26—C21—C22—C23	−1.3 (4)
C28—C27—C30—O6	−178.1 (3)	C20—C21—C22—C23	−173.2 (3)
C20—C27—C30—O6	0.8 (4)	C22—C21—C26—C25	2.1 (4)
C28—C27—C30—N8	−0.3 (4)	C20—C21—C26—C25	173.5 (3)
C20—C27—C30—N8	178.6 (2)	C21—C22—C23—C24	−1.0 (5)
C28—C27—C20—C21	61.2 (4)	C25—C24—C23—C22	2.6 (5)
C30—C27—C20—C21	−117.7 (3)	Cl2—C24—C23—C22	−176.9 (2)
C28—C27—C20—C33	−76.6 (4)	C3—C4—C5—C6	2.2 (5)
C30—C27—C20—C33	104.5 (3)	C3—C4—C5—Cl1	−178.1 (2)
C35—N10—C34—N12	173.9 (3)	C17—C14—C15—O4	179.5 (3)
C37—N10—C34—N12	−7.6 (4)	C1—C14—C15—O4	1.6 (5)
C35—N10—C34—C33	−6.8 (4)	C17—C14—C15—N4	−0.1 (5)
C37—N10—C34—C33	171.7 (3)	C1—C14—C15—N4	−178.1 (3)
N12—C34—C33—C36	−172.1 (3)	C2—C7—C6—C5	1.3 (5)
N10—C34—C33—C36	8.6 (4)	C4—C5—C6—C7	−3.1 (5)
N12—C34—C33—C20	5.7 (4)	Cl1—C5—C6—C7	177.1 (2)
N10—C34—C33—C20	−173.5 (2)	C17—N5—C16—O3	174.9 (3)
O8—C36—C33—C34	175.9 (3)	C19—N5—C16—O3	−2.8 (5)
N11—C36—C33—C34	−3.4 (4)	C17—N5—C16—N4	−5.8 (5)
O8—C36—C33—C20	−1.9 (4)	C19—N5—C16—N4	176.6 (3)
N11—C36—C33—C20	178.8 (2)	C23—C24—C25—C26	−1.9 (5)
C27—C20—C33—C34	−86.8 (3)	Cl2—C24—C25—C26	177.6 (2)
C21—C20—C33—C34	134.4 (3)	C21—C26—C25—C24	−0.5 (5)
C27—C20—C33—C36	90.9 (3)	O3—C16—N4—C15	179.6 (4)
C21—C20—C33—C36	−47.8 (4)	N5—C16—N4—C15	0.3 (5)
C16—N5—C17—N6	−173.1 (3)	O3—C16—N4—C18	0.2 (6)
C19—N5—C17—N6	4.4 (4)	N5—C16—N4—C18	−179.1 (4)
C16—N5—C17—C14	8.3 (4)	O4—C15—N4—C16	−177.1 (4)
C19—N5—C17—C14	−174.1 (3)	C14—C15—N4—C16	2.6 (5)
C15—C14—C17—N6	176.4 (3)	O4—C15—N4—C18	2.3 (6)
C1—C14—C17—N6	−5.9 (5)	C14—C15—N4—C18	−178.0 (4)
C15—C14—C17—N5	−5.2 (4)	C30—N8—C29—O5	176.4 (3)
C1—C14—C17—N5	172.5 (3)	C32—N8—C29—O5	−2.4 (5)
N3—C9—C8—C11	172.6 (3)	C30—N8—C29—N7	−3.1 (4)
N1—C9—C8—C11	−9.1 (4)	C32—N8—C29—N7	178.1 (3)
N3—C9—C8—C1	−7.9 (5)	C28—N7—C29—O5	−171.8 (3)
N1—C9—C8—C1	170.4 (3)	C31—N7—C29—O5	6.6 (5)
O1—C11—C8—C9	−175.7 (3)	C28—N7—C29—N8	7.7 (4)
N2—C11—C8—C9	2.7 (4)	C31—N7—C29—N8	−173.8 (3)
O1—C11—C8—C1	4.7 (5)	C29—N7—C28—N9	172.9 (3)
N2—C11—C8—C1	−176.8 (3)	C31—N7—C28—N9	−5.6 (4)
C14—C1—C8—C9	90.4 (3)	C29—N7—C28—C27	−8.8 (4)
C2—C1—C8—C9	−131.4 (3)	C31—N7—C28—C27	172.8 (3)
C14—C1—C8—C11	−90.1 (3)	C30—C27—C28—N9	−176.9 (3)
C2—C1—C8—C11	48.1 (4)	C20—C27—C28—N9	4.2 (5)
C27—C20—C21—C26	4.2 (4)	C30—C27—C28—N7	4.8 (4)
C33—C20—C21—C26	143.1 (3)	C20—C27—C28—N7	−174.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4	0.86	2.13	2.966 (4)	164
N3—H3B···O1ⁱ	0.86	2.26	3.059 (3)	154
N6—H6A···O6ⁱ	0.86	2.29	3.041 (3)	146
N6—H6B···O1	0.86	1.93	2.761 (3)	161
N9—H9A···O4ⁱⁱ	0.86	2.51	3.243 (4)	144
N9—H9B···O8	0.86	1.98	2.799 (3)	159
N12—H12A···O6	0.86	2.09	2.924 (3)	163
N12—H12B···O8ⁱⁱ	0.86	2.32	3.106 (3)	153
C1—H1···O4	0.98	2.22	2.794 (4)	116
C1—H1···N3	0.98	2.41	2.887 (4)	109
C12—H12C···O1ⁱ	0.96	2.45	3.164 (4)	131
C12—H12D···O2	0.96	2.27	2.708 (4)	107
C12—H12D···O5ⁱⁱⁱ	0.96	2.60	3.322 (4)	133
C13—H13A···O2	0.96	2.36	2.713 (4)	101
C18—H18B···O4	0.96	2.24	2.673 (6)	106
C19—H19B···O3	0.96	2.23	2.650 (5)	105
C20—H20···O6	0.98	2.23	2.807 (4)	116
C20—H20···N12	0.98	2.41	2.876 (4)	108
C31—H31B···O5	0.96	2.27	2.715 (5)	108
C32—H32A···O5	0.96	2.33	2.711 (5)	103
C37—H37A···O8ⁱⁱ	0.96	2.57	3.208 (4)	124
C37—H37C···O7	0.96	2.28	2.707 (4)	106
C38—H38B···O8	0.96	2.27	2.699 (4)	106

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

Experimental details

Crystal data
Chemical formula	C₁₉H₂₁ClN₆O₄
M_r	432.87
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	11.5365 (3), 14.5935 (4), 23.2102 (6)
V (Å³)	3907.62 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.40 × 0.28 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	53787, 9742, 6901
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.166, 1.06
No. of reflections	9742
No. of parameters	549
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.27, −0.28
Absolute structure	Flack (1983), 4345 Friedel pairs
Absolute structure parameter	0.15 (8)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4	0.8600	2.1300	2.966 (4)	164.00
N3—H3B···O1ⁱ	0.8600	2.2600	3.059 (3)	154.00
N6—H6A···O6ⁱ	0.8600	2.2900	3.041 (3)	146.00
N6—H6B···O1	0.8600	1.9300	2.761 (3)	161.00
N9—H9A···O4ⁱⁱ	0.8600	2.5100	3.243 (4)	144.00
N9—H9B···O8	0.8600	1.9800	2.799 (3)	159.00
N12—H12A···O6	0.8600	2.0900	2.924 (3)	163.00
N12—H12B···O8ⁱⁱ	0.8600	2.3200	3.106 (3)	153.00
C1—H1···O4	0.9800	2.2200	2.794 (4)	116.00
C1—H1···N3	0.9800	2.4100	2.887 (4)	109.00
C12—H12C···O1ⁱ	0.9600	2.4500	3.164 (4)	131.00
C12—H12D···O2	0.9600	2.2700	2.708 (4)	107.00
C12—H12D···O5ⁱⁱⁱ	0.9600	2.6000	3.322 (4)	133.00
C13—H13A···O2	0.9600	2.3600	2.713 (4)	101.00
C18—H18B···O4	0.9600	2.2400	2.673 (6)	106.00
C19—H19B···O3	0.9600	2.2300	2.650 (5)	105.00
C20—H20···O6	0.9800	2.2300	2.807 (4)	116.00
C20—H20···N12	0.9800	2.4100	2.876 (4)	108.00
C31—H31B···O5	0.9600	2.2700	2.715 (5)	108.00
C32—H32A···O5	0.9600	2.3300	2.711 (5)	103.00
C37—H37A···O8ⁱⁱ	0.9600	2.5700	3.208 (4)	124.00
C37—H37C···O7	0.9600	2.2800	2.707 (4)	106.00
C38—H38B···O8	0.9600	2.2700	2.699 (4)	106.00

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

Acknowledgements

AJT thanks the Council of Scientific and Industrial Research (CSIR), New Delhi, India, for financial support. The authors are grateful to Mr Sanchay Jyoti Bora, Pandu College, Guwahati, India for his suggestions.

References

Blicke, F. F. & Godt, H. C. (1954). J. Am. Chem. Soc. 76, 2798–2800. CrossRef CAS Web of Science Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Das, S., Saikia, B. K., Sridhar, B. & Thakur, A. J. (2008). Acta Cryst. E64, o1662. Web of Science CSD CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Jain, K. S., Chitre, T. S., Miniyar, P. B., Kathiravan, M. K., Bendre, V. S., Veer, V. S., Shahane, S. R. & Shishoo, C. J. (2006). Curr. Sci. 90, 793–803. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zheng, M., Deng, Y., Qiu, S., Luo, X., Chen, K., Liu, H. & Jiang, H. (2007). Bioorg. Med. Chem. Lett. 17, 2414–2420. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 65| Part 10| October 2009| Pages o2416-o2417

doi:10.1107/S1600536809035818

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

6,6′-Di­amino-1,1′,3,3′-tetra­methyl-5,5′-(4-chloro­benzyl­­idene)bis­­[pyrimidine-2,4(1H,3H)-dione]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6,6′-Diamino-1,1′,3,3′-tetramethyl-5,5′-(4-chlorobenzylidene)bis[pyrimidine-2,4(1H,3H)-dione]