


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811012918/xu5177sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536811012918/xu5177Isup2.hkl |
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean
(C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.037
- wR factor = 0.095
- Data-to-parameter ratio = 10.0
checkCIF/PLATON results
No syntax errors found
Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.390 From the CIF: _refine_ls_abs_structure_Flack_su 0.080 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.11 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Uiso(max)/Uiso(min) .. 4.29 Ratio PLAT234_ALERT_4_C Large Hirshfeld Difference C16 -- C17 .. 0.25 Ang. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 2 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.595 6 PLAT915_ALERT_3_C Low Friedel Pair Coverage ...................... 81 Perc.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.03 From the CIF: _reflns_number_total 3011 Count of symmetry unique reflns 1671 Completeness (_total/calc) 180.19% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1340 Fraction of Friedel pairs measured 0.802 Are heavy atom types Z>Si present yes PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 6 PLAT003_ALERT_2_G Number of Uiso or Uij Restrained Atom Sites .... 6 PLAT033_ALERT_4_G Flack x Parameter Value Deviates from Zero ..... 0.39 PLAT242_ALERT_2_G Check Low Ueq as Compared to Neighbors for C16' PLAT301_ALERT_3_G Note: Main Residue Disorder ................... 10 Perc. PLAT432_ALERT_2_G Short Inter X...Y Contact O3 .. C15 .. 2.91 Ang. PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 42 PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still 73 Perc.
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 8 ALERT level C = Check. Ensure it is not caused by an omission or oversight 9 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 7 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A solution of 3,5-dinitrobenzoyl chloride (0.01 mol) in anhydrous acetone (75 ml) and 3% tetrabutylammonium bromide (TBAB) as a phase-transfer catalyst (PTC) in anhydrous acetone was added dropwise to a suspension of dry potassium thiocyanate (0.01 mol) in acetone (50 ml) and the reaction mixture was refluxed for 50 min. After cooling to room temperature, a solution of ethyl-orthoamino benzoate (0.01 mol) in anhydrous acetone (25 ml) was added dropwise and the resulting mixture refluxed for 3 h. Hydrochloric acid (0.1 N, 300 ml) was added, and the solution was filtered. The solid product was washed with water and purified by re-crystallization from ethyl acetate.
N-bound H-atoms were located in a difference Fourier map and refined isotropically. Other H atoms were placed at geometrical positions with C—H = 0.93–0.97 Å and refined using riding model with Uiso(H) =1.2Ueq(C). The ethoxy group is disordered over two sites, the occupancy ratio was refined to 0.580 (15):0.420 (15). Distance and displacement restraints were used for the disordered components.
The background to this study has been set in our previous work on the structural chemistry of N,N'-disubstituted thiourea (Saeed et al., 2010). Herein, as a continuation of these studies, the structure of the title compound, (I), C17H14N4O7S, is described.
The compound is slightly twisted. The nitro groups are 3.9 (5)° and 17 (1)° from the phenyl ring plane of C10—C15. The thiourea plane is making a dihedral angle of 5.3 (2)° with the amido group and makes a dihedral angle of 31.35 (17)° with the phenyl ring plane of C2—C7.
There are inter-molecular N—H···O H-bond interactions which link the molecules to form 1-D chain in the crystal lattice. There are also weak π···π between neighbouring rings in the crystal lattice.
For background to this study and a related structure, see: Saeed et al. (2010).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
C17H14N4O7S | F(000) = 864 |
Mr = 418.38 | Dx = 1.461 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 6458 reflections |
a = 11.7264 (19) Å | θ = 2.1–25.0° |
b = 16.617 (3) Å | µ = 0.22 mm−1 |
c = 9.9630 (16) Å | T = 299 K |
β = 101.522 (2)° | Block, yellow |
V = 1902.3 (5) Å3 | 0.27 × 0.16 × 0.08 mm |
Z = 4 |
Bruker SMART 1000 CCD diffractometer | 3011 independent reflections |
Radiation source: fine-focus sealed tube | 2727 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
ω and φ scans | θmax = 25.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −13→13 |
Tmin = 0.943, Tmax = 0.983 | k = −19→15 |
4944 measured reflections | l = −11→11 |
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)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0536P)2 + 0.3273P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
3011 reflections | Δρmax = 0.22 e Å−3 |
301 parameters | Δρmin = −0.24 e Å−3 |
42 restraints | Absolute structure: Flack (1983), 1340 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.39 (8) |
C17H14N4O7S | V = 1902.3 (5) Å3 |
Mr = 418.38 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 11.7264 (19) Å | µ = 0.22 mm−1 |
b = 16.617 (3) Å | T = 299 K |
c = 9.9630 (16) Å | 0.27 × 0.16 × 0.08 mm |
β = 101.522 (2)° |
Bruker SMART 1000 CCD diffractometer | 3011 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 2727 reflections with I > 2σ(I) |
Tmin = 0.943, Tmax = 0.983 | Rint = 0.014 |
4944 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.095 | Δρmax = 0.22 e Å−3 |
S = 1.10 | Δρmin = −0.24 e Å−3 |
3011 reflections | Absolute structure: Flack (1983), 1340 Friedel pairs |
301 parameters | Absolute structure parameter: 0.39 (8) |
42 restraints |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.94150 (8) | 0.19793 (4) | 0.68183 (8) | 0.0759 (3) | |
O2 | 0.8103 (2) | 0.05570 (13) | 1.0967 (3) | 0.0866 (7) | |
O3 | 0.99391 (19) | −0.01499 (10) | 0.97679 (18) | 0.0663 (5) | |
O4 | 1.0187 (3) | −0.31100 (14) | 0.9255 (4) | 0.1022 (8) | |
O5 | 1.1263 (3) | −0.35915 (14) | 0.7937 (3) | 0.1095 (10) | |
O6 | 1.2496 (4) | −0.1832 (2) | 0.4646 (3) | 0.1355 (14) | |
O7 | 1.2710 (4) | −0.0571 (3) | 0.5114 (4) | 0.1459 (15) | |
N1 | 0.9176 (2) | 0.13747 (12) | 0.9269 (2) | 0.0543 (5) | |
H1 | 0.911 (2) | 0.0912 (17) | 0.974 (3) | 0.064 (8)* | |
H2 | 0.997 (2) | 0.0472 (15) | 0.704 (3) | 0.045 (7)* | |
N2 | 0.9902 (2) | 0.05353 (12) | 0.7789 (2) | 0.0555 (5) | |
N3 | 1.0798 (3) | −0.30348 (14) | 0.8423 (3) | 0.0773 (8) | |
N4 | 1.2402 (3) | −0.1244 (3) | 0.5338 (3) | 0.0976 (10) | |
C1 | 0.7736 (3) | 0.11786 (17) | 1.1281 (3) | 0.0647 (7) | |
C2 | 0.8103 (2) | 0.19844 (15) | 1.0865 (3) | 0.0563 (6) | |
C3 | 0.7770 (3) | 0.26756 (18) | 1.1485 (3) | 0.0713 (8) | |
H3 | 0.7296 | 0.2626 | 1.2125 | 0.086* | |
C4 | 0.8124 (4) | 0.3418 (2) | 1.1176 (4) | 0.0842 (10) | |
H4 | 0.7885 | 0.3870 | 1.1596 | 0.101* | |
C5 | 0.8830 (3) | 0.35007 (17) | 1.0248 (3) | 0.0782 (9) | |
H5 | 0.9080 | 0.4010 | 1.0051 | 0.094* | |
C6 | 0.9179 (3) | 0.28322 (16) | 0.9596 (3) | 0.0657 (7) | |
H6 | 0.9662 | 0.2896 | 0.8968 | 0.079* | |
C7 | 0.8809 (2) | 0.20717 (14) | 0.9882 (2) | 0.0531 (6) | |
C8 | 0.9476 (2) | 0.13033 (14) | 0.8043 (3) | 0.0525 (6) | |
C9 | 1.0156 (2) | −0.01157 (13) | 0.8622 (2) | 0.0518 (6) | |
C10 | 1.0713 (2) | −0.08065 (14) | 0.8043 (3) | 0.0539 (6) | |
C11 | 1.0528 (2) | −0.15737 (14) | 0.8509 (3) | 0.0555 (6) | |
H11 | 1.0103 | −0.1650 | 0.9193 | 0.067* | |
C12 | 1.0991 (2) | −0.22190 (15) | 0.7933 (3) | 0.0595 (7) | |
C13 | 1.1609 (3) | −0.21360 (18) | 0.6905 (3) | 0.0695 (8) | |
H13 | 1.1890 | −0.2582 | 0.6508 | 0.083* | |
C14 | 1.1797 (3) | −0.1366 (2) | 0.6489 (3) | 0.0677 (8) | |
C15 | 1.1379 (3) | −0.07002 (16) | 0.7053 (3) | 0.0618 (7) | |
H15 | 1.1542 | −0.0186 | 0.6775 | 0.074* | |
O1 | 0.7136 (10) | 0.1247 (5) | 1.2262 (9) | 0.083 (2) | 0.580 (15) |
C16 | 0.6730 (10) | 0.0532 (7) | 1.2838 (13) | 0.113 (4) | 0.580 (15) |
H16A | 0.6931 | 0.0548 | 1.3830 | 0.135* | 0.580 (15) |
H16B | 0.7077 | 0.0056 | 1.2523 | 0.135* | 0.580 (15) |
C17 | 0.5404 (10) | 0.0522 (6) | 1.2345 (19) | 0.161 (6) | 0.580 (15) |
H17A | 0.5070 | 0.0125 | 1.2851 | 0.193* | 0.580 (15) |
H17B | 0.5219 | 0.0392 | 1.1387 | 0.193* | 0.580 (15) |
H17C | 0.5093 | 0.1042 | 1.2489 | 0.193* | 0.580 (15) |
O1' | 0.6758 (12) | 0.1178 (7) | 1.1805 (14) | 0.085 (3) | 0.420 (15) |
C16' | 0.6436 (15) | 0.0411 (7) | 1.2287 (14) | 0.084 (4) | 0.420 (15) |
H16C | 0.7119 | 0.0073 | 1.2549 | 0.101* | 0.420 (15) |
H16D | 0.5889 | 0.0139 | 1.1571 | 0.101* | 0.420 (15) |
C17' | 0.5883 (19) | 0.0568 (8) | 1.3511 (18) | 0.134 (6) | 0.420 (15) |
H17D | 0.5738 | 0.0065 | 1.3920 | 0.161* | 0.420 (15) |
H17E | 0.5162 | 0.0850 | 1.3219 | 0.161* | 0.420 (15) |
H17F | 0.6399 | 0.0888 | 1.4169 | 0.161* | 0.420 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.1117 (6) | 0.0590 (4) | 0.0655 (4) | 0.0263 (4) | 0.0381 (4) | 0.0158 (3) |
O2 | 0.1105 (17) | 0.0589 (12) | 0.1056 (17) | 0.0112 (11) | 0.0580 (14) | 0.0120 (11) |
O3 | 0.1054 (16) | 0.0478 (10) | 0.0498 (10) | 0.0112 (9) | 0.0252 (10) | −0.0004 (7) |
O4 | 0.131 (2) | 0.0570 (13) | 0.122 (2) | −0.0046 (13) | 0.031 (2) | 0.0083 (13) |
O5 | 0.118 (2) | 0.0524 (12) | 0.153 (3) | 0.0257 (13) | 0.0147 (19) | −0.0192 (14) |
O6 | 0.172 (3) | 0.163 (3) | 0.0823 (18) | 0.073 (3) | 0.052 (2) | −0.0065 (18) |
O7 | 0.179 (4) | 0.131 (3) | 0.163 (3) | 0.028 (3) | 0.119 (3) | 0.026 (2) |
N1 | 0.0734 (15) | 0.0413 (10) | 0.0509 (12) | 0.0056 (9) | 0.0185 (10) | −0.0003 (8) |
N2 | 0.0776 (15) | 0.0480 (11) | 0.0434 (12) | 0.0094 (10) | 0.0178 (11) | −0.0029 (9) |
N3 | 0.0820 (18) | 0.0479 (13) | 0.092 (2) | 0.0105 (12) | −0.0056 (16) | −0.0079 (13) |
N4 | 0.099 (2) | 0.123 (3) | 0.0795 (19) | 0.049 (2) | 0.0396 (17) | 0.0068 (19) |
C1 | 0.076 (2) | 0.0658 (17) | 0.0559 (15) | 0.0108 (14) | 0.0209 (14) | 0.0059 (12) |
C2 | 0.0635 (17) | 0.0569 (14) | 0.0459 (13) | 0.0114 (11) | 0.0046 (12) | −0.0053 (10) |
C3 | 0.081 (2) | 0.0679 (18) | 0.0663 (18) | 0.0144 (14) | 0.0178 (16) | −0.0096 (14) |
C4 | 0.103 (3) | 0.0639 (19) | 0.086 (2) | 0.0187 (17) | 0.0186 (19) | −0.0250 (16) |
C5 | 0.103 (2) | 0.0453 (14) | 0.084 (2) | 0.0031 (14) | 0.0121 (18) | −0.0134 (13) |
C6 | 0.080 (2) | 0.0526 (14) | 0.0644 (17) | −0.0012 (12) | 0.0144 (15) | −0.0065 (12) |
C7 | 0.0631 (16) | 0.0459 (12) | 0.0478 (13) | 0.0070 (10) | 0.0049 (12) | −0.0029 (10) |
C8 | 0.0577 (15) | 0.0476 (13) | 0.0520 (13) | 0.0034 (10) | 0.0100 (11) | −0.0010 (10) |
C9 | 0.0643 (17) | 0.0453 (13) | 0.0462 (14) | 0.0029 (10) | 0.0119 (12) | −0.0023 (10) |
C10 | 0.0649 (17) | 0.0507 (13) | 0.0445 (12) | 0.0062 (11) | 0.0069 (12) | −0.0030 (10) |
C11 | 0.0637 (17) | 0.0486 (13) | 0.0516 (13) | 0.0047 (11) | 0.0056 (12) | −0.0062 (10) |
C12 | 0.0622 (17) | 0.0462 (13) | 0.0641 (17) | 0.0098 (11) | −0.0015 (14) | −0.0033 (11) |
C13 | 0.0718 (19) | 0.0740 (18) | 0.0574 (16) | 0.0290 (14) | 0.0001 (14) | −0.0162 (14) |
C14 | 0.0655 (18) | 0.082 (2) | 0.0568 (16) | 0.0240 (14) | 0.0151 (14) | 0.0023 (14) |
C15 | 0.0686 (18) | 0.0592 (14) | 0.0581 (15) | 0.0113 (13) | 0.0138 (13) | 0.0029 (12) |
O1 | 0.103 (6) | 0.083 (3) | 0.075 (4) | 0.006 (3) | 0.043 (4) | 0.008 (3) |
C16 | 0.130 (8) | 0.116 (7) | 0.104 (7) | −0.012 (5) | 0.053 (6) | 0.018 (5) |
C17 | 0.191 (12) | 0.086 (5) | 0.212 (14) | −0.002 (6) | 0.056 (10) | 0.002 (7) |
O1' | 0.087 (6) | 0.081 (4) | 0.093 (7) | 0.005 (4) | 0.035 (5) | −0.008 (4) |
C16' | 0.090 (7) | 0.070 (5) | 0.108 (8) | −0.013 (4) | 0.055 (6) | 0.007 (5) |
C17' | 0.209 (14) | 0.092 (7) | 0.135 (10) | 0.039 (8) | 0.116 (10) | 0.024 (7) |
S1—C8 | 1.649 (2) | C6—C7 | 1.385 (4) |
O2—C1 | 1.185 (3) | C6—H6 | 0.9300 |
O3—C9 | 1.219 (3) | C9—C10 | 1.493 (3) |
O4—N3 | 1.205 (4) | C10—C15 | 1.386 (4) |
O5—N3 | 1.222 (4) | C10—C11 | 1.388 (3) |
O6—N4 | 1.213 (4) | C11—C12 | 1.377 (4) |
O7—N4 | 1.210 (5) | C11—H11 | 0.9300 |
N1—C8 | 1.342 (3) | C12—C13 | 1.375 (4) |
N1—C7 | 1.416 (3) | C13—C14 | 1.376 (5) |
N1—H1 | 0.91 (3) | C13—H13 | 0.9300 |
N2—C9 | 1.360 (3) | C14—C15 | 1.375 (4) |
N2—C8 | 1.412 (3) | C15—H15 | 0.9300 |
N2—H2 | 0.77 (3) | O1—C16 | 1.442 (8) |
N3—C12 | 1.474 (4) | C16—C17 | 1.535 (9) |
N4—C14 | 1.478 (4) | C16—H16A | 0.9700 |
C1—O1 | 1.318 (10) | C16—H16B | 0.9700 |
C1—O1' | 1.351 (14) | C17—H17A | 0.9600 |
C1—C2 | 1.490 (4) | C17—H17B | 0.9600 |
C2—C3 | 1.396 (4) | C17—H17C | 0.9600 |
C2—C7 | 1.410 (4) | O1'—C16' | 1.440 (9) |
C3—C4 | 1.356 (5) | C16'—C17' | 1.514 (9) |
C3—H3 | 0.9300 | C16'—H16C | 0.9700 |
C4—C5 | 1.365 (5) | C16'—H16D | 0.9700 |
C4—H4 | 0.9300 | C17'—H17D | 0.9600 |
C5—C6 | 1.389 (4) | C17'—H17E | 0.9600 |
C5—H5 | 0.9300 | C17'—H17F | 0.9600 |
C8—N1—C7 | 128.5 (2) | N2—C9—C10 | 115.8 (2) |
C8—N1—H1 | 117.1 (18) | C15—C10—C11 | 120.2 (2) |
C7—N1—H1 | 114.0 (18) | C15—C10—C9 | 122.0 (2) |
C9—N2—C8 | 130.7 (2) | C11—C10—C9 | 117.9 (2) |
C9—N2—H2 | 115.4 (18) | C12—C11—C10 | 118.4 (3) |
C8—N2—H2 | 113.8 (19) | C12—C11—H11 | 120.8 |
O4—N3—O5 | 124.6 (3) | C10—C11—H11 | 120.8 |
O4—N3—C12 | 118.4 (2) | C13—C12—C11 | 122.8 (3) |
O5—N3—C12 | 117.1 (3) | C13—C12—N3 | 118.5 (2) |
O7—N4—O6 | 125.1 (4) | C11—C12—N3 | 118.6 (3) |
O7—N4—C14 | 118.6 (3) | C12—C13—C14 | 117.2 (2) |
O6—N4—C14 | 116.2 (4) | C12—C13—H13 | 121.4 |
O2—C1—O1 | 123.2 (5) | C14—C13—H13 | 121.4 |
O2—C1—O1' | 118.9 (6) | C15—C14—C13 | 122.3 (3) |
O2—C1—C2 | 124.7 (3) | C15—C14—N4 | 118.1 (3) |
O1—C1—C2 | 110.8 (4) | C13—C14—N4 | 119.5 (3) |
O1'—C1—C2 | 115.0 (5) | C14—C15—C10 | 119.0 (3) |
C3—C2—C7 | 118.5 (2) | C14—C15—H15 | 120.5 |
C3—C2—C1 | 119.6 (3) | C10—C15—H15 | 120.5 |
C7—C2—C1 | 121.9 (2) | C1—O1—C16 | 119.4 (9) |
C4—C3—C2 | 121.5 (3) | O1—C16—C17 | 106.0 (9) |
C4—C3—H3 | 119.2 | O1—C16—H16A | 110.5 |
C2—C3—H3 | 119.2 | C17—C16—H16A | 110.5 |
C3—C4—C5 | 120.0 (3) | O1—C16—H16B | 110.5 |
C3—C4—H4 | 120.0 | C17—C16—H16B | 110.5 |
C5—C4—H4 | 120.0 | H16A—C16—H16B | 108.7 |
C4—C5—C6 | 120.7 (3) | C1—O1'—C16' | 115.3 (10) |
C4—C5—H5 | 119.6 | O1'—C16'—C17' | 107.4 (10) |
C6—C5—H5 | 119.6 | O1'—C16'—H16C | 110.2 |
C7—C6—C5 | 120.0 (3) | C17'—C16'—H16C | 110.2 |
C7—C6—H6 | 120.0 | O1'—C16'—H16D | 110.2 |
C5—C6—H6 | 120.0 | C17'—C16'—H16D | 110.2 |
C6—C7—C2 | 119.3 (2) | H16C—C16'—H16D | 108.5 |
C6—C7—N1 | 121.5 (2) | C16'—C17'—H17D | 109.5 |
C2—C7—N1 | 119.1 (2) | C16'—C17'—H17E | 109.5 |
N1—C8—N2 | 114.2 (2) | H17D—C17'—H17E | 109.5 |
N1—C8—S1 | 129.22 (19) | C16'—C17'—H17F | 109.5 |
N2—C8—S1 | 116.62 (19) | H17D—C17'—H17F | 109.5 |
O3—C9—N2 | 123.2 (2) | H17E—C17'—H17F | 109.5 |
O3—C9—C10 | 121.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.91 (3) | 1.95 (3) | 2.672 (3) | 134 (2) |
N1—H1···O3 | 0.91 (3) | 2.01 (3) | 2.700 (3) | 131 (2) |
N2—H2···O3i | 0.77 (3) | 2.32 (3) | 3.086 (3) | 172 (2) |
Symmetry code: (i) x, −y, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H14N4O7S |
Mr | 418.38 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 299 |
a, b, c (Å) | 11.7264 (19), 16.617 (3), 9.9630 (16) |
β (°) | 101.522 (2) |
V (Å3) | 1902.3 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.27 × 0.16 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.943, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4944, 3011, 2727 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.095, 1.10 |
No. of reflections | 3011 |
No. of parameters | 301 |
No. of restraints | 42 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.24 |
Absolute structure | Flack (1983), 1340 Friedel pairs |
Absolute structure parameter | 0.39 (8) |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and Mercury (Macrae et al., 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.91 (3) | 1.95 (3) | 2.672 (3) | 134 (2) |
N1—H1···O3 | 0.91 (3) | 2.01 (3) | 2.700 (3) | 131 (2) |
N2—H2···O3i | 0.77 (3) | 2.32 (3) | 3.086 (3) | 172 (2) |
Symmetry code: (i) x, −y, z−1/2. |
The background to this study has been set in our previous work on the structural chemistry of N,N'-disubstituted thiourea (Saeed et al., 2010). Herein, as a continuation of these studies, the structure of the title compound, (I), C17H14N4O7S, is described.
The compound is slightly twisted. The nitro groups are 3.9 (5)° and 17 (1)° from the phenyl ring plane of C10—C15. The thiourea plane is making a dihedral angle of 5.3 (2)° with the amido group and makes a dihedral angle of 31.35 (17)° with the phenyl ring plane of C2—C7.
There are inter-molecular N—H···O H-bond interactions which link the molecules to form 1-D chain in the crystal lattice. There are also weak π···π between neighbouring rings in the crystal lattice.