Ethyl 2-{N-[N-(4-chloro-6-methoxy­pyrimidin-2-yl)carbamo­yl]sulfamo­yl}benzoate

Lu, C.; Li, F.-S.; Yu, D.-S.; Yao, W.; Liu, Y.-H.

doi:10.1107/S1600536808017029

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1248

doi:10.1107/S1600536808017029

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Ethyl 2-{N-[N-(4-chloro-6-methoxypyrimidin-2-yl)carbamoyl]sulfamoyl}benzoate

Chui Lu,^a Fang-Shi Li,^a ^* Da-Sheng Yu,^a Wei Yao ^a and Yin-Hong Liu ^a

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technolgy, No. 5 Xinmofan Road, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: fangshi.li@njut.edu.cn

(Received 3 June 2008; accepted 5 June 2008; online 13 June 2008)

The asymmetric unit of the title compound, C₁₅H₁₅ClN₄O₆S, contains two independent molecules, in which the pyrimidine and benzene rings are oriented at dihedral angles of 75.21 (3) and 86.00 (3)°. Intramolecular N—H⋯N and C—H⋯O hydrogen bonds result in the formation of two five- and two six-membered rings. The six-membered rings have flattened-boat conformations, while the five-membered rings adopt envelope conformations. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules.

Related literature

For related literature, see: Zhao et al. (2006 ); Li & Liu (1995 ). For bond-length data, see: Allen et al. (1987 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₅H₁₅ClN₄O₆S
M_r = 414.83
Triclinic, $[P \overline 1]$
a = 7.8210 (16) Å
b = 12.310 (3) Å
c = 20.200 (4) Å
α = 94.97 (3)°
β = 97.58 (3)°
γ = 93.76 (3)°
V = 1914.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 298 (2) K
0.40 × 0.30 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.873, T_max = 0.966
7430 measured reflections
6882 independent reflections
3809 reflections with I > 2σ(I)
R_int = 0.069
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.088
wR(F²) = 0.209
S = 1.07
6882 reflections
451 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.92 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N3	0.86	1.96	2.648 (6)	136
N2—H2A⋯O5ⁱ	0.86	2.00	2.831 (8)	162
N5—H5B⋯N7	0.86	1.96	2.651 (6)	136
N6—H6B⋯O2ⁱⁱ	0.86	2.14	2.973 (7)	162
C8—H8A⋯O4	0.93	2.43	2.821 (6)	105
C21—H21A⋯O9	0.93	2.44	2.848 (8)	107
Symmetry codes: (i) -x+1, -y+2, -z; (ii) x-1, y, z.

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, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017029/hk2471sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808017029/hk2471Isup2.hkl

checkCIF report

Comment top

The title compound, (I), is a highly effective postemergence sulfonylurea herbicide used to control many annual broadleaf weeds in soybean fields (Zhao et al., 2006). As part of our studies in this area, we report herein its crystal structure.

The asymmetric unit of (I) (Fig. 1) contains two independent molecules. The bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C4-C9), B (N3/N4/C11-C14) and C (C19-C24), D (N7/N8/C26-C29) are, of course, planar, and the dihedral angles between them are A/B = 75.21 (3)° and C/D = 86.00 (3)°. The intramolecular N-H···N and C-H···O hydrogen bonds (Table 1) result in the formation of two five- and two six-membered rings: E (N1-N3/C10/C11/H1A), F (S1/O4/C8/C9/H8A), G (N5-N7/C25/C26/H5B) and H (S2/O9/C20/C21/H21A). Rings E and G adopt flattened-boat conformations, having total puckering amplitudes, Q_T, of 0.139 (3) and 0.117 (3) Å (Cremer & Pople, 1975), while rings F and H have envelope conformations, with O4 and O9 atoms displaced by 0.291 (3) and -0.182 (3) Å from the planes of the other ring atoms, respectively.

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For related literature, see: Zhao et al. (2006); Li & Liu (1995). For bond-length data, see: Allen et al. (1987). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound, (I), was prepared according to the literature method (Li & Liu, 1995). Crystals suitable for X-ray analysis were obtained by dissolving (I) (0.1 g) in acetonitrile (25 ml) and evaporating the solvent slowly at room temperature for about 7 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme.
	Fig. 2. A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines.

Ethyl 2-{N-[N-(4-chloro-6-methoxypyrimidin-2-yl)carbamoyl]sulfamoyl}benzoate top

Crystal data top

C₁₅H₁₅ClN₄O₆S	Z = 4
M_r = 414.83	F(000) = 856
Triclinic, P1	D_x = 1.439 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8210 (16) Å	Cell parameters from 25 reflections
b = 12.310 (3) Å	θ = 10–13°
c = 20.200 (4) Å	µ = 0.35 mm⁻¹
α = 94.97 (3)°	T = 298 K
β = 97.58 (3)°	Block, colorless
γ = 93.76 (3)°	0.40 × 0.30 × 0.10 mm
V = 1914.7 (7) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	3809 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.069
Graphite monochromator	θ_max = 25.2°, θ_min = 1.0°
ω/2θ scans	h = −9→9
Absorption correction: ψ scan (North et al., 1968)	k = −14→14
T_min = 0.873, T_max = 0.966	l = 0→24
7430 measured reflections	3 standard reflections every 120 min
6882 independent reflections	intensity decay: none

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)] = 0.088	H-atom parameters constrained
wR(F²) = 0.209	w = 1/[σ²(F_o²) + (0.06P)² + 3P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
6882 reflections	Δρ_max = 0.39 e Å⁻³
451 parameters	Δρ_min = −0.92 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₅ClN₄O₆S	γ = 93.76 (3)°
M_r = 414.83	V = 1914.7 (7) Å³
Triclinic, P1	Z = 4
a = 7.8210 (16) Å	Mo Kα radiation
b = 12.310 (3) Å	µ = 0.35 mm⁻¹
c = 20.200 (4) Å	T = 298 K
α = 94.97 (3)°	0.40 × 0.30 × 0.10 mm
β = 97.58 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	3809 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.069
T_min = 0.873, T_max = 0.966	3 standard reflections every 120 min
7430 measured reflections	intensity decay: none
6882 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.088	451 parameters
wR(F²) = 0.209	H-atom parameters constrained
S = 1.07	Δρ_max = 0.39 e Å⁻³
6882 reflections	Δρ_min = −0.92 e Å⁻³

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 > 2sigma(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	0.2819 (3)	1.35508 (17)	0.20491 (14)	0.1456 (9)
Cl2	−0.2214 (4)	1.36337 (15)	0.18268 (12)	0.1378 (9)
S1	0.30971 (16)	0.69683 (11)	0.07830 (8)	0.0633 (4)
S2	−0.4009 (2)	1.21087 (14)	0.41116 (9)	0.0851 (5)
O1	0.6496 (7)	0.6052 (5)	0.2354 (3)	0.121
O2	0.5614 (6)	0.7692 (4)	0.2171 (2)	0.1023 (14)
O3	0.2506 (5)	0.6505 (3)	0.1335 (2)	0.0809 (11)
O4	0.2122 (5)	0.6758 (3)	0.0137 (2)	0.0790 (11)
O5	0.4435 (4)	0.8758 (3)	0.00933 (17)	0.0617 (9)
O6	0.1314 (6)	0.9834 (4)	0.27791 (19)	0.0895 (12)
O7	0.1026 (6)	1.3566 (4)	0.4533 (2)	0.1042 (14)
O8	−0.0191 (6)	1.2479 (4)	0.3635 (2)	0.0983 (14)
O9	−0.5648 (6)	1.1767 (5)	0.4287 (3)	0.1230 (18)
O10	−0.3643 (6)	1.3245 (4)	0.4050 (2)	0.1082 (15)
O11	−0.4315 (5)	0.9729 (3)	0.3604 (2)	0.0879 (12)
O12	−0.1102 (5)	1.0051 (3)	0.0628 (2)	0.087
N1	0.3246 (5)	0.8291 (3)	0.0994 (2)	0.0621 (11)
H1A	0.2927	0.8530	0.1368	0.074*
N2	0.3823 (5)	1.0128 (3)	0.0822 (2)	0.0562 (10)
H2A	0.4246	1.0587	0.0578	0.067*
N3	0.2572 (5)	0.9970 (4)	0.1804 (2)	0.0645 (11)
N4	0.3277 (5)	1.1683 (4)	0.1435 (2)	0.0727 (12)
N5	−0.3771 (5)	1.1487 (4)	0.3380 (2)	0.0696 (12)
H5B	−0.3591	1.1887	0.3064	0.084*
N6	−0.3321 (5)	1.0026 (4)	0.2635 (2)	0.0664 (11)
H6B	−0.3406	0.9328	0.2543	0.080*
N7	−0.2656 (6)	1.1691 (4)	0.2210 (2)	0.0780 (13)
N8	−0.2204 (5)	0.9995 (4)	0.1625 (2)	0.0710 (12)
C1	0.7097 (10)	0.5750 (6)	0.3555 (4)	0.110
H1B	0.6547	0.5830	0.3953	0.166*
H1C	0.8283	0.6036	0.3658	0.166*
H1D	0.7048	0.4989	0.3396	0.166*
C2	0.6224 (10)	0.6335 (6)	0.3050 (3)	0.105
H2B	0.6568	0.7108	0.3163	0.127*
H2C	0.4993	0.6235	0.3071	0.127*
C3	0.6109 (8)	0.6821 (5)	0.1952 (4)	0.0849 (19)
C4	0.6389 (7)	0.6488 (4)	0.1286 (4)	0.0716 (15)
C5	0.8039 (7)	0.6113 (4)	0.1169 (4)	0.087 (2)
H5A	0.8878	0.6041	0.1530	0.104*
C6	0.8363 (9)	0.5873 (5)	0.0558 (6)	0.103 (3)
H6A	0.9405	0.5580	0.0498	0.123*
C7	0.7241 (9)	0.6033 (5)	0.0002 (4)	0.095 (2)
H7A	0.7559	0.5902	−0.0424	0.113*
C8	0.5624 (7)	0.6392 (4)	0.0077 (4)	0.0794 (17)
H8A	0.4828	0.6478	−0.0296	0.095*
C9	0.5227 (6)	0.6617 (4)	0.0718 (3)	0.0610 (13)
C10	0.3871 (6)	0.9035 (4)	0.0590 (3)	0.0562 (12)
C11	0.3213 (6)	1.0596 (4)	0.1379 (3)	0.0585 (12)
C12	0.2003 (7)	1.0443 (5)	0.2328 (3)	0.0688 (15)
C13	0.2059 (8)	1.1576 (6)	0.2442 (3)	0.0843 (18)
H13A	0.1685	1.1925	0.2818	0.101*
C14	0.2698 (8)	1.2139 (5)	0.1968 (3)	0.0809 (17)
C15	0.1267 (10)	0.8714 (7)	0.2624 (4)	0.113 (2)
H15A	0.0762	0.8347	0.2960	0.169*
H15B	0.2422	0.8502	0.2610	0.169*
H15C	0.0584	0.8515	0.2195	0.169*
C16	0.2150 (10)	1.5357 (6)	0.4433 (4)	0.119
H16A	0.2730	1.5823	0.4161	0.178*
H16B	0.2847	1.5350	0.4861	0.178*
H16C	0.1053	1.5626	0.4497	0.178*
C17	0.1872 (10)	1.4226 (6)	0.4092 (4)	0.110
H17A	0.1149	1.4217	0.3662	0.132*
H17B	0.2969	1.3947	0.4017	0.132*
C18	0.0078 (8)	1.2714 (5)	0.4211 (3)	0.0780 (16)
C19	−0.0646 (8)	1.2030 (5)	0.4724 (3)	0.0746 (15)
C20	−0.2409 (8)	1.1672 (5)	0.4701 (3)	0.0764 (15)
C21	−0.2891 (9)	1.1016 (5)	0.5153 (3)	0.0913 (18)
H21A	−0.4058	1.0800	0.5142	0.110*
C22	−0.1676 (12)	1.0649 (6)	0.5642 (4)	0.110 (2)
H22A	−0.2028	1.0171	0.5939	0.132*
C23	−0.0037 (11)	1.0987 (7)	0.5676 (4)	0.109 (2)
H23A	0.0758	1.0747	0.6005	0.131*
C24	0.0571 (10)	1.1704 (6)	0.5229 (4)	0.106 (2)
H24A	0.1734	1.1950	0.5270	0.127*
C25	−0.3841 (7)	1.0362 (5)	0.3238 (3)	0.0684 (14)
C26	−0.2682 (6)	1.0601 (5)	0.2143 (3)	0.0675 (13)
C27	−0.2115 (9)	1.2230 (6)	0.1711 (4)	0.0914 (18)
C28	−0.1619 (9)	1.1722 (6)	0.1197 (4)	0.0905 (18)
H28A	−0.1251	1.2107	0.0859	0.109*
C29	−0.1637 (7)	1.0629 (5)	0.1155 (3)	0.0747 (15)
C30	−0.1119 (5)	0.8938 (3)	0.0581 (2)	0.0413 (10)
H30A	−0.0725	0.8680	0.0170	0.062*
H30B	−0.2276	0.8629	0.0587	0.062*
H30C	−0.0369	0.8720	0.0954	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.163 (2)	0.0865 (13)	0.183 (2)	−0.0031 (13)	0.0484 (17)	−0.0403 (14)
Cl2	0.199 (2)	0.0701 (12)	0.1447 (19)	0.0120 (13)	0.0191 (16)	0.0190 (11)
S1	0.0420 (7)	0.0561 (8)	0.0927 (10)	−0.0030 (6)	0.0109 (7)	0.0143 (7)
S2	0.0714 (10)	0.0853 (12)	0.0964 (12)	0.0066 (8)	0.0153 (9)	−0.0094 (9)
O1	0.121	0.121	0.121	0.009	0.017	0.012
O2	0.131 (4)	0.064 (3)	0.109 (3)	0.008 (3)	0.009 (3)	−0.001 (2)
O3	0.066 (2)	0.070 (2)	0.113 (3)	0.0030 (19)	0.025 (2)	0.030 (2)
O4	0.071 (3)	0.078 (3)	0.085 (3)	−0.009 (2)	0.007 (2)	0.010 (2)
O5	0.058 (2)	0.060 (2)	0.069 (2)	0.0027 (16)	0.0199 (18)	0.0014 (17)
O6	0.092 (3)	0.121 (4)	0.062 (2)	0.027 (3)	0.018 (2)	0.018 (2)
O7	0.100 (3)	0.094 (3)	0.112 (4)	−0.023 (3)	0.021 (3)	−0.013 (3)
O8	0.099 (3)	0.114 (4)	0.077 (3)	−0.015 (3)	0.014 (2)	−0.007 (3)
O9	0.072 (3)	0.151 (5)	0.145 (4)	−0.003 (3)	0.041 (3)	−0.026 (3)
O10	0.109 (4)	0.072 (3)	0.134 (4)	0.019 (3)	−0.010 (3)	−0.019 (3)
O11	0.093 (3)	0.082 (3)	0.088 (3)	−0.017 (2)	0.018 (2)	0.011 (2)
O12	0.087	0.087	0.087	0.007	0.012	0.008
N1	0.050 (2)	0.060 (3)	0.081 (3)	0.013 (2)	0.017 (2)	0.012 (2)
N2	0.045 (2)	0.059 (3)	0.066 (3)	0.0026 (19)	0.0112 (19)	0.010 (2)
N3	0.051 (3)	0.082 (3)	0.061 (3)	0.020 (2)	0.002 (2)	0.009 (2)
N4	0.054 (3)	0.066 (3)	0.093 (3)	−0.002 (2)	0.005 (2)	−0.010 (3)
N5	0.068 (3)	0.072 (3)	0.064 (3)	0.006 (2)	−0.005 (2)	−0.002 (2)
N6	0.067 (3)	0.065 (3)	0.063 (3)	0.000 (2)	−0.005 (2)	0.010 (2)
N7	0.082 (3)	0.078 (3)	0.073 (3)	0.004 (3)	0.002 (2)	0.014 (2)
N8	0.053 (3)	0.088 (3)	0.067 (3)	0.004 (2)	−0.007 (2)	0.005 (2)
C1	0.110	0.110	0.110	0.009	0.015	0.011
C2	0.105	0.105	0.105	0.008	0.015	0.010
C3	0.079 (4)	0.062 (4)	0.109 (5)	0.000 (3)	−0.015 (4)	0.034 (4)
C4	0.051 (3)	0.045 (3)	0.116 (5)	−0.002 (2)	0.002 (3)	0.012 (3)
C5	0.048 (3)	0.047 (3)	0.164 (7)	−0.004 (3)	0.015 (4)	0.001 (4)
C6	0.048 (4)	0.056 (4)	0.205 (9)	0.000 (3)	0.043 (5)	−0.019 (5)
C7	0.071 (4)	0.052 (3)	0.163 (7)	−0.015 (3)	0.057 (5)	−0.021 (4)
C8	0.060 (4)	0.058 (3)	0.120 (5)	−0.009 (3)	0.014 (3)	0.013 (3)
C9	0.049 (3)	0.041 (3)	0.090 (4)	−0.011 (2)	0.010 (3)	0.005 (3)
C10	0.036 (3)	0.056 (3)	0.077 (4)	0.010 (2)	0.005 (2)	0.014 (3)
C11	0.043 (3)	0.066 (3)	0.063 (3)	0.005 (2)	−0.004 (2)	0.004 (3)
C12	0.052 (3)	0.098 (5)	0.054 (3)	0.014 (3)	−0.003 (3)	0.006 (3)
C13	0.067 (4)	0.113 (6)	0.069 (4)	0.015 (4)	0.007 (3)	−0.017 (4)
C14	0.069 (4)	0.079 (4)	0.086 (4)	0.000 (3)	−0.006 (3)	−0.013 (3)
C15	0.126 (6)	0.122 (7)	0.096 (5)	−0.004 (5)	0.026 (4)	0.037 (5)
C16	0.119	0.119	0.119	0.009	0.016	0.011
C17	0.110	0.110	0.110	0.009	0.015	0.011
C18	0.064 (4)	0.082 (4)	0.084 (4)	−0.007 (3)	0.012 (3)	−0.007 (3)
C19	0.078 (4)	0.080 (4)	0.065 (3)	−0.009 (3)	0.017 (3)	0.001 (3)
C20	0.076 (3)	0.075 (4)	0.074 (3)	−0.006 (3)	0.008 (3)	−0.006 (3)
C21	0.094 (4)	0.095 (4)	0.083 (4)	−0.019 (3)	0.025 (3)	0.001 (3)
C22	0.138 (5)	0.110 (5)	0.075 (4)	−0.012 (4)	0.008 (4)	0.006 (3)
C23	0.127 (5)	0.117 (5)	0.079 (4)	0.015 (4)	−0.008 (4)	0.015 (4)
C24	0.094 (4)	0.114 (5)	0.099 (5)	−0.002 (4)	−0.010 (3)	−0.005 (4)
C25	0.056 (3)	0.074 (4)	0.073 (4)	0.002 (3)	−0.002 (3)	0.011 (3)
C26	0.042 (3)	0.091 (4)	0.064 (3)	−0.002 (3)	−0.004 (2)	0.003 (3)
C27	0.088 (4)	0.101 (4)	0.082 (4)	0.012 (3)	−0.004 (3)	0.013 (3)
C28	0.092 (4)	0.086 (4)	0.090 (4)	−0.002 (3)	0.004 (3)	0.017 (3)
C29	0.058 (3)	0.099 (4)	0.063 (3)	0.010 (3)	−0.005 (3)	0.002 (3)
C30	0.030 (2)	0.050 (3)	0.041 (2)	0.0020 (18)	0.0019 (17)	−0.0027 (18)

Geometric parameters (Å, º) top

Cl1—C14	1.727 (7)	Cl2—C27	1.732 (7)
S1—O3	1.413 (4)	S2—O9	1.421 (5)
S1—O4	1.416 (4)	S2—O10	1.429 (5)
S1—N1	1.639 (4)	S2—N5	1.643 (4)
S1—C9	1.767 (5)	S2—C20	1.755 (6)
O1—C3	1.325 (7)	O7—C18	1.314 (7)
O1—C2	1.464 (8)	O7—C17	1.450 (8)
O2—C3	1.230 (8)	O8—C18	1.161 (7)
O5—C10	1.180 (6)	O11—C25	1.195 (6)
O6—C12	1.370 (7)	O12—C29	1.356 (6)
O6—C15	1.384 (8)	O12—C30	1.364 (5)
N1—C10	1.386 (6)	N5—C25	1.385 (7)
N1—H1A	0.8600	N5—H5B	0.8600
N2—C11	1.374 (6)	N6—C25	1.373 (7)
N2—C10	1.391 (6)	N6—C26	1.395 (7)
N2—H2A	0.8600	N6—H6B	0.8600
N3—C12	1.306 (6)	N7—C26	1.335 (7)
N3—C11	1.327 (6)	N7—C27	1.352 (8)
N4—C14	1.319 (7)	N8—C26	1.341 (7)
N4—C11	1.331 (6)	N8—C29	1.380 (7)
C1—C2	1.427 (7)	C16—C17	1.488 (9)
C1—H1B	0.9600	C16—H16A	0.9600
C1—H1C	0.9600	C16—H16B	0.9600
C1—H1D	0.9600	C16—H16C	0.9600
C2—H2B	0.9700	C17—H17A	0.9700
C2—H2C	0.9700	C17—H17B	0.9700
C3—C4	1.422 (9)	C18—C19	1.533 (8)
C4—C9	1.393 (8)	C19—C24	1.404 (9)
C4—C5	1.440 (8)	C19—C20	1.413 (8)
C5—C6	1.305 (10)	C20—C21	1.344 (8)
C5—H5A	0.9300	C21—C22	1.403 (10)
C6—C7	1.369 (10)	C21—H21A	0.9300
C6—H6A	0.9300	C22—C23	1.313 (10)
C7—C8	1.389 (8)	C22—H22A	0.9300
C7—H7A	0.9300	C23—C24	1.420 (10)
C8—C9	1.381 (8)	C23—H23A	0.9300
C8—H8A	0.9300	C24—H24A	0.9300
C12—C13	1.391 (8)	C27—C28	1.282 (9)
C13—C14	1.357 (8)	C28—C29	1.339 (8)
C13—H13A	0.9300	C28—H28A	0.9300
C15—H15A	0.9600	C30—H30A	0.9600
C15—H15B	0.9600	C30—H30B	0.9600
C15—H15C	0.9600	C30—H30C	0.9600

O3—S1—O4	120.0 (2)	O9—S2—O10	118.1 (3)
O3—S1—N1	104.5 (2)	O9—S2—N5	109.7 (3)
O4—S1—N1	108.2 (2)	O10—S2—N5	104.9 (3)
O3—S1—C9	109.6 (2)	O9—S2—C20	107.9 (3)
O4—S1—C9	107.6 (3)	O10—S2—C20	109.1 (3)
N1—S1—C9	106.0 (2)	N5—S2—C20	106.5 (2)
C3—O1—C2	113.9 (6)	C18—O7—C17	113.0 (5)
C12—O6—C15	114.6 (5)	C29—O12—C30	121.9 (5)
C10—N1—S1	122.1 (4)	C25—N5—S2	124.5 (4)
C10—N1—H1A	119.0	C25—N5—H5B	117.8
S1—N1—H1A	119.0	S2—N5—H5B	117.8
C11—N2—C10	130.6 (4)	C25—N6—C26	132.3 (5)
C11—N2—H2A	114.7	C25—N6—H6B	113.9
C10—N2—H2A	114.7	C26—N6—H6B	113.9
C12—N3—C11	118.6 (5)	C26—N7—C27	117.3 (5)
C14—N4—C11	115.5 (5)	C26—N8—C29	112.1 (5)
C2—C1—H1B	109.5	C17—C16—H16A	109.5
C2—C1—H1C	109.5	C17—C16—H16B	109.5
H1B—C1—H1C	109.5	H16A—C16—H16B	109.5
C2—C1—H1D	109.5	C17—C16—H16C	109.5
H1B—C1—H1D	109.5	H16A—C16—H16C	109.5
H1C—C1—H1D	109.5	H16B—C16—H16C	109.5
C1—C2—O1	117.7 (6)	O7—C17—C16	106.5 (6)
C1—C2—H2B	107.9	O7—C17—H17A	110.4
O1—C2—H2B	107.9	C16—C17—H17A	110.4
C1—C2—H2C	107.9	O7—C17—H17B	110.4
O1—C2—H2C	107.9	C16—C17—H17B	110.4
H2B—C2—H2C	107.2	H17A—C17—H17B	108.6
O2—C3—O1	120.8 (7)	O8—C18—O7	127.7 (6)
O2—C3—C4	128.4 (6)	O8—C18—C19	123.5 (6)
O1—C3—C4	110.8 (6)	O7—C18—C19	108.8 (5)
C9—C4—C3	123.8 (5)	C24—C19—C20	119.1 (6)
C9—C4—C5	116.4 (6)	C24—C19—C18	116.2 (6)
C3—C4—C5	119.4 (6)	C20—C19—C18	124.6 (6)
C6—C5—C4	120.4 (7)	C21—C20—C19	119.8 (6)
C6—C5—H5A	119.8	C21—C20—S2	118.8 (5)
C4—C5—H5A	119.8	C19—C20—S2	121.3 (5)
C5—C6—C7	123.0 (6)	C20—C21—C22	121.6 (7)
C5—C6—H6A	118.5	C20—C21—H21A	119.2
C7—C6—H6A	118.5	C22—C21—H21A	119.2
C6—C7—C8	119.6 (7)	C23—C22—C21	119.3 (7)
C6—C7—H7A	120.2	C23—C22—H22A	120.3
C8—C7—H7A	120.2	C21—C22—H22A	120.3
C9—C8—C7	118.4 (7)	C22—C23—C24	122.6 (8)
C9—C8—H8A	120.8	C22—C23—H23A	118.7
C7—C8—H8A	120.8	C24—C23—H23A	118.7
C8—C9—C4	122.1 (5)	C19—C24—C23	117.6 (7)
C8—C9—S1	116.4 (4)	C19—C24—H24A	121.2
C4—C9—S1	121.3 (4)	C23—C24—H24A	121.2
O5—C10—N1	122.3 (5)	O11—C25—N6	122.1 (6)
O5—C10—N2	122.7 (5)	O11—C25—N5	123.4 (6)
N1—C10—N2	114.9 (5)	N6—C25—N5	114.4 (5)
N3—C11—N4	124.6 (5)	N7—C26—N8	125.6 (5)
N3—C11—N2	120.2 (5)	N7—C26—N6	118.2 (5)
N4—C11—N2	115.2 (5)	N8—C26—N6	116.1 (5)
N3—C12—O6	120.8 (6)	C28—C27—N7	121.7 (7)
N3—C12—C13	121.3 (6)	C28—C27—Cl2	124.5 (6)
O6—C12—C13	117.9 (5)	N7—C27—Cl2	113.9 (5)
C14—C13—C12	115.4 (5)	C27—C28—C29	119.2 (7)
C14—C13—H13A	122.3	C27—C28—H28A	120.4
C12—C13—H13A	122.3	C29—C28—H28A	120.4
N4—C14—C13	124.6 (6)	C28—C29—O12	121.7 (6)
N4—C14—Cl1	115.5 (5)	C28—C29—N8	124.1 (6)
C13—C14—Cl1	119.9 (5)	O12—C29—N8	114.2 (6)
O6—C15—H15A	109.5	O12—C30—H30A	109.5
O6—C15—H15B	109.5	O12—C30—H30B	109.5
H15A—C15—H15B	109.5	H30A—C30—H30B	109.5
O6—C15—H15C	109.5	O12—C30—H30C	109.5
H15A—C15—H15C	109.5	H30A—C30—H30C	109.5
H15B—C15—H15C	109.5	H30B—C30—H30C	109.5

O3—S1—N1—C10	176.9 (4)	O9—S2—N5—C25	−58.7 (5)
O4—S1—N1—C10	−54.2 (4)	O10—S2—N5—C25	173.5 (4)
C9—S1—N1—C10	61.1 (4)	C20—S2—N5—C25	57.8 (5)
C3—O1—C2—C1	−160.3 (6)	C18—O7—C17—C16	153.5 (6)
C2—O1—C3—O2	1.8 (9)	C17—O7—C18—O8	−3.6 (10)
C2—O1—C3—C4	−179.5 (5)	C17—O7—C18—C19	175.9 (5)
O2—C3—C4—C9	−46.4 (9)	O8—C18—C19—C24	125.1 (7)
O1—C3—C4—C9	135.0 (6)	O7—C18—C19—C24	−54.4 (7)
O2—C3—C4—C5	125.9 (7)	O8—C18—C19—C20	−51.7 (9)
O1—C3—C4—C5	−52.6 (7)	O7—C18—C19—C20	128.8 (6)
C9—C4—C5—C6	−2.5 (8)	C24—C19—C20—C21	−1.0 (8)
C3—C4—C5—C6	−175.4 (6)	C18—C19—C20—C21	175.7 (6)
C4—C5—C6—C7	4.8 (10)	C24—C19—C20—S2	176.5 (5)
C5—C6—C7—C8	−4.8 (10)	C18—C19—C20—S2	−6.7 (7)
C6—C7—C8—C9	2.5 (8)	O9—S2—C20—C21	7.4 (5)
C7—C8—C9—C4	−0.4 (8)	O10—S2—C20—C21	136.8 (5)
C7—C8—C9—S1	−175.3 (4)	N5—S2—C20—C21	−110.4 (5)
C3—C4—C9—C8	172.9 (5)	O9—S2—C20—C19	−170.2 (4)
C5—C4—C9—C8	0.4 (7)	O10—S2—C20—C19	−40.8 (5)
C3—C4—C9—S1	−12.5 (7)	N5—S2—C20—C19	72.1 (5)
C5—C4—C9—S1	175.0 (4)	C19—C20—C21—C22	−1.7 (9)
O3—S1—C9—C8	142.1 (4)	S2—C20—C21—C22	−179.3 (5)
O4—S1—C9—C8	10.0 (4)	C20—C21—C22—C23	2.6 (11)
N1—S1—C9—C8	−105.7 (4)	C21—C22—C23—C24	−0.8 (12)
O3—S1—C9—C4	−32.8 (5)	C20—C19—C24—C23	2.7 (9)
O4—S1—C9—C4	−164.9 (4)	C18—C19—C24—C23	−174.3 (6)
N1—S1—C9—C4	79.4 (4)	C22—C23—C24—C19	−1.8 (11)
S1—N1—C10—O5	−5.1 (7)	C26—N6—C25—O11	−177.9 (5)
S1—N1—C10—N2	176.5 (3)	C26—N6—C25—N5	2.3 (8)
C11—N2—C10—O5	179.5 (5)	S2—N5—C25—O11	10.6 (8)
C11—N2—C10—N1	−2.1 (7)	S2—N5—C25—N6	−169.5 (4)
C12—N3—C11—N4	−2.0 (7)	C27—N7—C26—N8	0.6 (8)
C12—N3—C11—N2	180.0 (4)	C27—N7—C26—N6	−176.7 (5)
C14—N4—C11—N3	2.1 (7)	C29—N8—C26—N7	0.9 (7)
C14—N4—C11—N2	−179.8 (4)	C29—N8—C26—N6	178.2 (4)
C10—N2—C11—N3	1.8 (7)	C25—N6—C26—N7	−6.2 (8)
C10—N2—C11—N4	−176.4 (4)	C25—N6—C26—N8	176.3 (5)
C11—N3—C12—O6	179.4 (4)	C26—N7—C27—C28	−1.1 (9)
C11—N3—C12—C13	0.0 (7)	C26—N7—C27—Cl2	177.4 (4)
C15—O6—C12—N3	−0.7 (8)	N7—C27—C28—C29	0.0 (11)
C15—O6—C12—C13	178.6 (6)	Cl2—C27—C28—C29	−178.3 (5)
N3—C12—C13—C14	1.6 (8)	C27—C28—C29—O12	−179.0 (6)
O6—C12—C13—C14	−177.8 (5)	C27—C28—C29—N8	1.7 (10)
C11—N4—C14—C13	−0.3 (8)	C30—O12—C29—C28	−180.0 (5)
C11—N4—C14—Cl1	178.8 (4)	C30—O12—C29—N8	−0.6 (7)
C12—C13—C14—N4	−1.5 (9)	C26—N8—C29—C28	−2.1 (8)
C12—C13—C14—Cl1	179.5 (4)	C26—N8—C29—O12	178.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3	0.86	1.96	2.648 (6)	136
N2—H2A···O5ⁱ	0.86	2.00	2.831 (8)	162
N5—H5B···N7	0.86	1.96	2.651 (6)	136
N6—H6B···O2ⁱⁱ	0.86	2.14	2.973 (7)	162
C8—H8A···O4	0.93	2.43	2.821 (6)	105
C21—H21A···O9	0.93	2.44	2.848 (8)	107

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅ClN₄O₆S
M_r	414.83
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.8210 (16), 12.310 (3), 20.200 (4)
α, β, γ (°)	94.97 (3), 97.58 (3), 93.76 (3)
V (Å³)	1914.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.40 × 0.30 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.873, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	7430, 6882, 3809
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.088, 0.209, 1.07
No. of reflections	6882
No. of parameters	451
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.92

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3	0.86	1.96	2.648 (6)	136.00
N2—H2A···O5ⁱ	0.86	2.00	2.831 (8)	162.00
N5—H5B···N7	0.86	1.96	2.651 (6)	136.00
N6—H6B···O2ⁱⁱ	0.86	2.14	2.973 (7)	162.00
C8—H8A···O4	0.93	2.43	2.821 (6)	105.00
C21—H21A···O9	0.93	2.44	2.848 (8)	107.00

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Li, B. & Liu, C. L. (1995). Nongyao, 34, 36–37. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, J., Yi, G. X., He, S. P., Wang, B. M., Yu, C. X., Li, G., Zhai, Z. X., Li, Z. H. & Li, Q. X. (2006). J. Agric. Food Chem. 54, 4948–4953. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 64| Part 7| July 2008| Page o1248

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

Ethyl 2-{N-[N-(4-chloro-6-meth­oxy­pyrimidin-2-yl)carbamo­yl]sulfamo­yl}benzoate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

Ethyl 2-{N-[N-(4-chloro-6-methoxypyrimidin-2-yl)carbamoyl]sulfamoyl}benzoate