2-[3-(4-Methoxy­benzo­yl)thio­ureido]-3-methyl­butyric acid

Mol­ecules of the title compound, C₁₄H₁₈N₂O₄S, are linked into a linear chain, which propagates along the a axis of the triclinic unit cell through inter­molecular hydrogen bonding between the carboxyl group and the thioxo S atom.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.062
• wR factor = 0.162
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT301_ALERT_3_C Main Residue  Disorder .........................      16.00 Perc.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1N    ..  H2      ..       1.95 Ang.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1N    ..  H2'     ..       1.99 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1N    ...          ?
PLAT731_ALERT_1_C Bond    Calc     0.86(3), Rep   0.850(10) ......       3.00 su-Rat
              O1   -H1O     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(3), Rep   0.850(10) ......       3.00 su-Rat
              O1   -H1O     1.555   1.555

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

   3 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.

2-[3-(4-Methoxybenzoyl)thioureido]-3-methylbutyric acid

Crystal data

C14H18N2O4S	Z = 2
Mr = 310.36	F(000) = 328
Triclinic, P1	Dx = 1.332 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.051 (1) Å	Cell parameters from 679 reflections
b = 8.084 (1) Å	θ = 1.6–22.2°
c = 13.205 (2) Å	µ = 0.23 mm^−1
α = 83.741 (2)°	T = 295 K
β = 80.164 (3)°	Block, colourless
γ = 66.162 (2)°	0.31 × 0.16 × 0.12 mm
V = 773.8 (2) Å^3

Data collection

Bruker APEX area-detector diffractometer	2078 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 27.5°, θmin = 1.6°
φ and ω scans	h = −10→10
8876 measured reflections	k = −10→10
3509 independent reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0853P)^2] where P = (Fo^2 + 2Fc^2)/3
3509 reflections	(Δ/σ)max = 0.001
242 parameters	Δρmax = 0.29 e Å^−3
26 restraints	Δρmin = −0.15 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.4504 (1)	0.48898 (9)	0.87273 (5)	0.0644 (3)
O1	0.3998 (3)	−0.1208 (2)	0.9046 (2)	0.083 (1)
O2	0.3324 (3)	−0.0243 (2)	0.7472 (2)	0.073 (1)
O3	0.2455 (3)	0.4241 (2)	0.5866 (1)	0.067 (1)
O4	0.1847 (4)	1.1160 (3)	0.2984 (2)	0.092 (1)
N1	0.3413 (3)	0.5650 (3)	0.6893 (2)	0.055 (1)
N2	0.3243 (3)	0.3060 (3)	0.7749 (2)	0.049 (1)
C1	0.2619 (3)	0.7037 (3)	0.5225 (2)	0.048 (1)
C4	0.2144 (4)	0.9845 (3)	0.3740 (2)	0.061 (1)
C2'	0.256 (2)	0.870 (1)	0.5441 (9)	0.047 (2)	0.42 (2)
C3'	0.232 (2)	1.013 (2)	0.4720 (7)	0.042 (2)	0.42 (2)
C5'	0.221 (2)	0.819 (1)	0.3471 (9)	0.061 (3)	0.42 (2)
C6'	0.244 (2)	0.683 (2)	0.4221 (6)	0.049 (2)	0.42 (2)
C2	0.324 (2)	0.837 (1)	0.5308 (7)	0.056 (2)	0.58 (2)
C3	0.300 (2)	0.977 (1)	0.4570 (6)	0.053 (2)	0.58 (2)
C5	0.151 (2)	0.851 (1)	0.3668 (8)	0.090 (3)	0.58 (2)
C6	0.174 (2)	0.711 (1)	0.4385 (7)	0.068 (2)	0.58 (2)
C7	0.2051 (5)	1.2756 (4)	0.3142 (2)	0.082 (1)
C8	0.2814 (3)	0.5513 (3)	0.5990 (2)	0.050 (1)
C9	0.3670 (3)	0.4472 (3)	0.7752 (2)	0.048 (1)
C10	0.3217 (3)	0.1865 (3)	0.8658 (2)	0.046 (1)
C11	0.1394 (4)	0.2697 (3)	0.9371 (2)	0.054 (1)
C12	−0.0224 (4)	0.2735 (5)	0.8913 (2)	0.083 (1)
C13	0.1460 (5)	0.1833 (4)	1.0451 (2)	0.085 (1)
C14	0.3521 (4)	0.0039 (3)	0.8307 (2)	0.055 (1)
H1o	0.400 (5)	−0.220 (3)	0.887 (2)	0.10 (1)*
H1n	0.361 (3)	0.658 (2)	0.696 (2)	0.05 (1)*
H2n	0.292 (3)	0.281 (3)	0.722 (1)	0.06 (1)*
H2'	0.2675	0.8867	0.6106	0.056*	0.42 (2)
H3'	0.2290	1.1226	0.4890	0.051*	0.42 (2)
H5'	0.2098	0.8021	0.2804	0.073*	0.42 (2)
H6'	0.2469	0.5728	0.4053	0.059*	0.42 (2)
H2	0.3827	0.8331	0.5865	0.067*	0.58 (2)
H3	0.3417	1.0670	0.4636	0.063*	0.58 (2)
H5	0.0912	0.8561	0.3115	0.108*	0.58 (2)
H6	0.1319	0.6220	0.4316	0.082*	0.58 (2)
H7a	0.1851	1.3536	0.2533	0.123*
H7b	0.3267	1.2459	0.3291	0.123*
H7c	0.1173	1.3363	0.3710	0.123*
H10	0.4224	0.1728	0.9028	0.056*
H11	0.1189	0.3963	0.9437	0.064*
H12a	−0.1344	0.3510	0.9299	0.124*
H12b	−0.0195	0.1532	0.8939	0.124*
H12c	−0.0157	0.3186	0.8211	0.124*
H13a	0.2445	0.1914	1.0734	0.127*
H13b	0.1658	0.0583	1.0427	0.127*
H13c	0.0320	0.2454	1.0875	0.127*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0977 (6)	0.0473 (4)	0.0649 (5)	−0.0397 (4)	−0.0344 (4)	0.0109 (3)
O1	0.143 (2)	0.041 (1)	0.075 (1)	−0.039 (1)	−0.041 (1)	0.008 (1)
O2	0.112 (2)	0.054 (1)	0.061 (1)	−0.036 (1)	−0.023 (1)	−0.010 (1)
O3	0.098 (2)	0.057 (1)	0.058 (1)	−0.038 (1)	−0.023 (1)	0.002 (1)
O4	0.157 (2)	0.079 (1)	0.057 (1)	−0.060 (2)	−0.039 (1)	0.022 (1)
N1	0.074 (2)	0.052 (1)	0.051 (1)	−0.035 (1)	−0.018 (1)	0.009 (1)
N2	0.068 (1)	0.043 (1)	0.041 (1)	−0.028 (1)	−0.010 (1)	−0.001 (1)
C1	0.052 (2)	0.050 (1)	0.039 (1)	−0.017 (1)	−0.004 (1)	−0.004 (1)
C4	0.084 (2)	0.061 (2)	0.040 (1)	−0.030 (2)	−0.011 (1)	0.0049 (12)
C2'	0.040 (5)	0.054 (4)	0.046 (4)	−0.016 (4)	−0.013 (4)	−0.004 (3)
C3'	0.028 (5)	0.040 (4)	0.055 (5)	−0.009 (4)	0.000 (4)	−0.007 (3)
C5'	0.083 (7)	0.062 (5)	0.042 (5)	−0.032 (5)	−0.003 (5)	−0.012 (4)
C6'	0.052 (6)	0.047 (4)	0.047 (5)	−0.020 (4)	0.003 (4)	−0.013 (3)
C2	0.056 (5)	0.071 (4)	0.047 (4)	−0.030 (4)	−0.019 (4)	0.013 (3)
C3	0.049 (5)	0.058 (4)	0.051 (3)	−0.023 (4)	−0.004 (3)	0.002 (3)
C5	0.165 (9)	0.088 (6)	0.041 (5)	−0.066 (6)	−0.044 (6)	0.010 (4)
C6	0.099 (7)	0.066 (5)	0.053 (4)	−0.042 (5)	−0.020 (4)	0.000 (3)
C7	0.107 (3)	0.064 (2)	0.069 (2)	−0.034 (2)	−0.010 (2)	0.016 (2)
C8	0.052 (2)	0.052 (1)	0.046 (1)	−0.021 (1)	−0.002 (1)	−0.002 (1)
C9	0.051 (1)	0.043 (1)	0.049 (1)	−0.019 (1)	−0.005 (1)	0.002 (1)
C10	0.061 (2)	0.037 (1)	0.046 (1)	−0.022 (1)	−0.012 (1)	0.002 (1)
C11	0.066 (2)	0.046 (1)	0.052 (2)	−0.025 (1)	−0.005 (1)	−0.001 (1)
C12	0.068 (2)	0.096 (2)	0.086 (2)	−0.035 (2)	−0.009 (2)	0.001 (2)
C13	0.105 (3)	0.091 (2)	0.055 (2)	−0.041 (2)	−0.002 (2)	0.007 (2)
C14	0.068 (2)	0.042 (1)	0.059 (2)	−0.024 (1)	−0.015 (1)	0.000 (1)

Geometric parameters (Å, º)

S1—C9	1.672 (3)	C11—C12	1.515 (4)
O1—C14	1.310 (3)	C11—C13	1.517 (3)
O2—C14	1.198 (3)	O1—H1o	0.85 (1)
O3—C8	1.209 (3)	N1—H1n	0.85 (1)
O4—C4	1.352 (3)	N2—H2n	0.85 (1)
O4—C7	1.406 (4)	C2'—H2'	0.93
N1—C9	1.386 (3)	C3'—H3'	0.93
N1—C8	1.391 (3)	C5'—H5'	0.93
N2—C9	1.319 (3)	C6'—H6'	0.93
N2—C10	1.459 (3)	C2—H2	0.93
C1—C2'	1.382 (8)	C3—H3	0.93
C1—C2	1.383 (7)	C5—H5	0.93
C1—C6'	1.393 (8)	C6—H6	0.93
C1—C6	1.397 (7)	C7—H7a	0.96
C1—C8	1.480 (3)	C7—H7b	0.96
C4—C3	1.375 (7)	C7—H7c	0.96
C4—C3'	1.380 (8)	C10—H10	0.98
C4—C5	1.388 (7)	C11—H11	0.98
C4—C5'	1.398 (8)	C12—H12a	0.96
C2'—C3'	1.385 (8)	C12—H12b	0.96
C5'—C6'	1.375 (8)	C12—H12c	0.96
C2—C3	1.384 (7)	C13—H13a	0.96
C5—C6	1.364 (7)	C13—H13b	0.96
C10—C14	1.508 (3)	C13—H13c	0.96
C10—C11	1.537 (3)
C4—O4—C7	118.8 (2)	C10—N2—H2n	115 (2)
C9—N1—C8	128.3 (2)	C1—C2'—H2'	118.2
C9—N2—C10	122.3 (2)	C3'—C2'—H2'	118.2
C2'—C1—C6'	116.7 (9)	C4—C3'—H3'	121.4
C2—C1—C6	119.3 (7)	C2'—C3'—H3'	121.4
C2'—C1—C8	124.4 (5)	C6'—C5'—H5'	121.0
C2—C1—C8	123.5 (4)	C4—C5'—H5'	121.0
C6'—C1—C8	118.8 (5)	C5'—C6'—H6'	118.8
C6—C1—C8	117.2 (4)	C1—C6'—H6'	118.8
O4—C4—C3	124.3 (4)	C3—C2—H2	119.7
O4—C4—C3'	122.4 (5)	C1—C2—H2	119.7
O4—C4—C5	117.0 (4)	C4—C3—H3	119.9
C3—C4—C5	118.7 (7)	C2—C3—H3	119.9
O4—C4—C5'	115.6 (5)	C6—C5—H5	119.0
C3'—C4—C5'	122.0 (9)	C4—C5—H5	119.0
C1—C2'—C3'	124 (1)	C5—C6—H6	120.4
C4—C3'—C2'	117.2 (9)	C1—C6—H6	120.4
C6'—C5'—C4	118 (1)	O4—C7—H7a	109.5
C5'—C6'—C1	122 (1)	O4—C7—H7b	109.5
C3—C2—C1	120.6 (7)	H7a—C7—H7b	109.5
C4—C3—C2	120.2 (7)	O4—C7—H7c	109.5
C6—C5—C4	122.0 (7)	H7a—C7—H7c	109.5
C5—C6—C1	119.1 (7)	H7b—C7—H7c	109.5
O3—C8—N1	121.2 (2)	N2—C10—H10	108.8
O3—C8—C1	123.5 (2)	C14—C10—H10	108.8
N1—C8—C1	115.3 (2)	C11—C10—H10	108.8
N2—C9—N1	117.3 (2)	C12—C11—H11	106.3
N2—C9—S1	123.4 (2)	C13—C11—H11	106.3
N1—C9—S1	119.2 (2)	C10—C11—H11	106.3
N2—C10—C14	108.3 (2)	C11—C12—H12a	109.5
N2—C10—C11	109.9 (2)	C11—C12—H12b	109.5
C14—C10—C11	112.2 (2)	H12a—C12—H12b	109.5
C12—C11—C13	111.9 (2)	C11—C12—H12c	109.5
C12—C11—C10	112.5 (2)	H12a—C12—H12c	109.5
C13—C11—C10	112.9 (2)	H12b—C12—H12c	109.5
O2—C14—O1	124.1 (2)	C11—C13—H13a	109.5
O2—C14—C10	125.0 (2)	C11—C13—H13b	109.5
O1—C14—C10	110.9 (2)	H13a—C13—H13b	109.5
C14—O1—H1o	110 (2)	C11—C13—H13c	109.5
C9—N1—H1n	113 (2)	H13a—C13—H13c	109.5
C8—N1—H1n	119 (2)	H13b—C13—H13c	109.5
C9—N2—H2n	122 (2)
C7—O4—C4—C3	−14.2 (8)	C9—N1—C8—O3	−0.7 (4)
C7—O4—C4—C3'	11.6 (7)	C9—N1—C8—C1	177.9 (2)
C7—O4—C4—C5	164.8 (7)	C2'—C1—C8—O3	162.5 (6)
C7—O4—C4—C5'	−170.1 (6)	C2—C1—C8—O3	−171.7 (7)
C2—C1—C2'—C3'	87 (2)	C6'—C1—C8—O3	−15.7 (6)
C6'—C1—C2'—C3'	0.0 (3)	C6—C1—C8—O3	8.9 (7)
C8—C1—C2'—C3'	−178.2 (3)	C2'—C1—C8—N1	−16.2 (6)
O4—C4—C3'—C2'	177.6 (3)	C2—C1—C8—N1	9.7 (7)
C5'—C4—C3'—C2'	−0.6 (6)	C6'—C1—C8—N1	165.6 (6)
C1—C2'—C3'—C4	0.2 (3)	C6—C1—C8—N1	−169.7 (7)
O4—C4—C5'—C6'	−177.5 (5)	C10—N2—C9—N1	−171.5 (2)
C3'—C4—C5'—C6'	0.7 (8)	C10—N2—C9—S1	8.8 (3)
C4—C5'—C6'—C1	−0.5 (8)	C8—N1—C9—N2	−2.6 (4)
C2'—C1—C6'—C5'	0.2 (6)	C8—N1—C9—S1	177.0 (2)
C8—C1—C6'—C5'	178.5 (5)	C9—N2—C10—C14	−155.1 (2)
C6—C1—C2—C3	0.0 (3)	C9—N2—C10—C11	82.0 (3)
C8—C1—C2—C3	−179.4 (2)	N2—C10—C11—C12	68.4 (3)
O4—C4—C3—C2	179.9 (3)	C14—C10—C11—C12	−52.1 (3)
C5—C4—C3—C2	0.9 (5)	N2—C10—C11—C13	−163.7 (2)
C1—C2—C3—C4	−0.4 (3)	C14—C10—C11—C13	75.7 (3)
O4—C4—C5—C6	179.8 (5)	N2—C10—C14—O2	−18.2 (4)
C3—C4—C5—C6	−1.2 (7)	C11—C10—C14—O2	103.3 (3)
C4—C5—C6—C1	0.8 (8)	N2—C10—C14—O1	163.1 (2)
C2—C1—C6—C5	−0.3 (6)	C11—C10—C14—O1	−75.4 (3)
C8—C1—C6—C5	179.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···S1^i	0.85 (1)	2.25 (1)	3.080 (2)	165 (3)
N2—H2n···O3	0.85 (1)	2.03 (2)	2.651 (3)	129 (2)

Symmetry code: (i) x, y−1, z.