3-[3-(4-Methoxy­benzo­yl)thio­ureido]propionic acid

In the title mol­ecule, C₁₂H₁₄N₂O₄S, the methoxy­benzoyl group is trans to the thiono S atom across the C—N bond. The propionic acid group adopts a gauche conformation about the C—C bond, with a C_COOH—C—C—N torsion angle of 64.9 (4)°. In the crystal structure, inter­molecular O—H...S, N—H...O and C—H...O hydrogen bonds link the mol­ecules into chains parallel to the c axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.043
• wR factor = 0.106
• Data-to-parameter ratio = 10.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

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           25.00
           From the CIF: _reflns_number_total               1792
           Count of symmetry unique reflns         1175
           Completeness (_total/calc)            152.51%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       617
           Fraction of Friedel pairs measured     0.525
           Are heavy atom types Z>Si present        yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

3-[3-(4-methoxybenzoyl)thioureido]propionic acid

Crystal data

C12H14N2O4S	F(000) = 296
Mr = 282.31	Dx = 1.411 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 636 reflections
a = 9.795 (3) Å	θ = 2.2–25.0°
b = 4.7790 (13) Å	µ = 0.26 mm^−1
c = 14.951 (4) Å	T = 298 K
β = 108.275 (5)°	Plate, yellow
V = 664.6 (3) Å^3	0.34 × 0.17 × 0.07 mm
Z = 2

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1792 independent reflections
Radiation source: fine-focus sealed tube	1660 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 83.66 pixels mm^-1	θmax = 25.0°, θmin = 2.2°
ω scans	h = −9→11
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −5→5
Tmin = 0.912, Tmax = 0.979	l = −17→17
3159 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0526P)^2 + 0.0617P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
1792 reflections	Δρmax = 0.28 e Å^−3
172 parameters	Δρmin = −0.15 e Å^−3
2 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.16 (11)

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

	x	y	z	Uiso*/Ueq
S1	0.38629 (10)	−0.38705 (19)	0.23542 (7)	0.0556 (3)
O1	1.0598 (3)	0.8691 (6)	0.50390 (19)	0.0666 (8)
O2	0.7374 (3)	0.0951 (6)	0.16476 (18)	0.0578 (7)
O3	0.2748 (3)	−0.0679 (6)	−0.15426 (19)	0.0621 (8)
H3	0.3022	0.0678	−0.1776	0.093*
O4	0.5042 (3)	−0.0904 (6)	−0.06790 (17)	0.0538 (7)
N1	0.6026 (3)	−0.0297 (6)	0.25707 (19)	0.0425 (7)
H1A	0.5864	0.0065	0.3092	0.051*
N2	0.5386 (3)	−0.2939 (6)	0.12120 (19)	0.0485 (7)
H2A	0.6072	−0.2080	0.1082	0.058*
C1	0.7862 (5)	0.3355 (9)	0.4027 (3)	0.0588 (11)
H1B	0.7216	0.2210	0.4197	0.071*
C2	0.8709 (5)	0.5207 (11)	0.4685 (3)	0.0634 (12)
H2B	0.8616	0.5314	0.5284	0.076*
C3	0.9684 (4)	0.6880 (8)	0.4451 (3)	0.0505 (9)
C4	0.9782 (4)	0.6750 (8)	0.3544 (3)	0.0511 (9)
H4A	1.0423	0.7910	0.3375	0.061*
C5	0.8940 (4)	0.4926 (8)	0.2899 (3)	0.0478 (9)
H5A	0.9025	0.4852	0.2297	0.057*
C6	0.7953 (4)	0.3170 (7)	0.3125 (2)	0.0427 (8)
C7	1.0561 (6)	0.8900 (11)	0.5985 (3)	0.0825 (16)
H7A	1.1255	1.0257	0.6322	0.124*
H7B	1.0785	0.7113	0.6289	0.124*
H7C	0.9619	0.9471	0.5979	0.124*
C8	0.7119 (4)	0.1219 (7)	0.2399 (2)	0.0416 (8)
C9	0.5164 (4)	−0.2310 (7)	0.2014 (2)	0.0421 (8)
C10	0.4560 (5)	−0.4982 (8)	0.0525 (3)	0.0547 (10)
H10A	0.4186	−0.6405	0.0849	0.066*
H10B	0.5189	−0.5892	0.0227	0.066*
C11	0.3323 (4)	−0.3616 (8)	−0.0223 (3)	0.0518 (9)
H11A	0.2744	−0.5058	−0.0622	0.062*
H11B	0.2720	−0.2635	0.0080	0.062*
C12	0.3816 (4)	−0.1610 (8)	−0.0818 (2)	0.0449 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0630 (6)	0.0511 (5)	0.0539 (5)	−0.0134 (5)	0.0201 (4)	−0.0049 (5)
O1	0.0608 (19)	0.0754 (19)	0.0603 (18)	−0.0264 (15)	0.0143 (15)	−0.0117 (14)
O2	0.0648 (18)	0.0664 (18)	0.0479 (15)	−0.0121 (14)	0.0259 (14)	−0.0057 (13)
O3	0.0499 (16)	0.080 (2)	0.0535 (15)	0.0136 (14)	0.0126 (14)	0.0121 (14)
O4	0.0448 (17)	0.0726 (19)	0.0435 (14)	−0.0013 (13)	0.0129 (12)	−0.0001 (12)
N1	0.0471 (18)	0.0452 (16)	0.0374 (15)	−0.0030 (14)	0.0163 (14)	−0.0023 (12)
N2	0.0588 (19)	0.0444 (17)	0.0419 (16)	−0.0022 (15)	0.0155 (14)	−0.0033 (13)
C1	0.058 (2)	0.074 (3)	0.048 (2)	−0.027 (2)	0.0215 (19)	−0.0061 (19)
C2	0.065 (3)	0.080 (3)	0.050 (2)	−0.027 (2)	0.024 (2)	−0.014 (2)
C3	0.040 (2)	0.056 (2)	0.051 (2)	−0.0034 (17)	0.0087 (17)	−0.0060 (17)
C4	0.048 (2)	0.052 (2)	0.056 (2)	−0.0097 (18)	0.0188 (18)	0.0008 (17)
C5	0.043 (2)	0.057 (2)	0.0442 (19)	0.0013 (17)	0.0156 (17)	0.0019 (17)
C6	0.0405 (19)	0.0427 (19)	0.0467 (19)	0.0014 (15)	0.0162 (16)	0.0009 (15)
C7	0.086 (4)	0.099 (4)	0.058 (3)	−0.039 (3)	0.015 (2)	−0.021 (3)
C8	0.038 (2)	0.0447 (19)	0.0403 (19)	0.0029 (15)	0.0101 (16)	0.0046 (15)
C9	0.046 (2)	0.0338 (17)	0.0397 (19)	0.0084 (16)	0.0043 (16)	0.0040 (15)
C10	0.071 (3)	0.042 (2)	0.050 (2)	−0.0024 (19)	0.017 (2)	−0.0061 (17)
C11	0.052 (2)	0.060 (2)	0.0434 (19)	−0.0089 (18)	0.0149 (17)	−0.0079 (17)
C12	0.048 (2)	0.050 (2)	0.0393 (18)	0.0042 (17)	0.0167 (17)	−0.0113 (15)

Geometric parameters (Å, º)

S1—C9	1.687 (4)	C2—H2B	0.9300
O1—C3	1.353 (4)	C3—C4	1.391 (5)
O1—C7	1.429 (5)	C4—C5	1.368 (5)
O2—C8	1.231 (4)	C4—H4A	0.9300
O3—C12	1.325 (4)	C5—C6	1.399 (5)
O3—H3	0.8200	C5—H5A	0.9300
O4—C12	1.201 (5)	C6—C8	1.470 (5)
N1—C9	1.375 (4)	C7—H7A	0.9600
N1—C8	1.382 (5)	C7—H7B	0.9600
N1—H1A	0.8600	C7—H7C	0.9600
N2—C9	1.318 (4)	C10—C11	1.515 (6)
N2—C10	1.463 (5)	C10—H10A	0.9700
N2—H2A	0.8600	C10—H10B	0.9700
C1—C6	1.381 (5)	C11—C12	1.488 (5)
C1—C2	1.389 (6)	C11—H11A	0.9700
C1—H1B	0.9300	C11—H11B	0.9700
C2—C3	1.372 (6)
C3—O1—C7	118.1 (3)	O1—C7—H7B	109.5
C12—O3—H3	109.5	H7A—C7—H7B	109.5
C9—N1—C8	128.2 (3)	O1—C7—H7C	109.5
C9—N1—H1A	115.9	H7A—C7—H7C	109.5
C8—N1—H1A	115.9	H7B—C7—H7C	109.5
C9—N2—C10	125.3 (3)	O2—C8—N1	120.4 (3)
C9—N2—H2A	117.4	O2—C8—C6	121.0 (3)
C10—N2—H2A	117.4	N1—C8—C6	118.6 (3)
C6—C1—C2	121.7 (4)	N2—C9—N1	117.7 (3)
C6—C1—H1B	119.2	N2—C9—S1	122.0 (3)
C2—C1—H1B	119.2	N1—C9—S1	120.3 (3)
C3—C2—C1	120.0 (4)	N2—C10—C11	111.7 (3)
C3—C2—H2B	120.0	N2—C10—H10A	109.3
C1—C2—H2B	120.0	C11—C10—H10A	109.3
O1—C3—C2	125.4 (3)	N2—C10—H10B	109.3
O1—C3—C4	115.4 (3)	C11—C10—H10B	109.3
C2—C3—C4	119.3 (3)	H10A—C10—H10B	108.0
C5—C4—C3	120.4 (3)	C12—C11—C10	112.6 (3)
C5—C4—H4A	119.8	C12—C11—H11A	109.1
C3—C4—H4A	119.8	C10—C11—H11A	109.1
C4—C5—C6	121.4 (3)	C12—C11—H11B	109.1
C4—C5—H5A	119.3	C10—C11—H11B	109.1
C6—C5—H5A	119.3	H11A—C11—H11B	107.8
C1—C6—C5	117.3 (3)	O4—C12—O3	122.5 (4)
C1—C6—C8	124.8 (3)	O4—C12—C11	124.9 (4)
C5—C6—C8	117.9 (3)	O3—C12—C11	112.6 (3)
O1—C7—H7A	109.5
C6—C1—C2—C3	−1.1 (7)	C9—N1—C8—C6	−176.7 (3)
C7—O1—C3—C2	0.2 (7)	C1—C6—C8—O2	−171.7 (4)
C7—O1—C3—C4	−179.4 (4)	C5—C6—C8—O2	6.7 (5)
C1—C2—C3—O1	−177.7 (4)	C1—C6—C8—N1	9.0 (5)
C1—C2—C3—C4	1.8 (7)	C5—C6—C8—N1	−172.6 (3)
O1—C3—C4—C5	178.0 (4)	C10—N2—C9—N1	−178.8 (3)
C2—C3—C4—C5	−1.6 (6)	C10—N2—C9—S1	0.6 (5)
C3—C4—C5—C6	0.6 (6)	C8—N1—C9—N2	0.5 (5)
C2—C1—C6—C5	0.1 (6)	C8—N1—C9—S1	−178.9 (3)
C2—C1—C6—C8	178.5 (4)	N2—C10—C11—C12	64.9 (4)
C4—C5—C6—C1	0.1 (6)	C10—C11—C12—O4	−7.0 (5)
C4—C5—C6—C8	−178.4 (3)	C10—C11—C12—O3	172.2 (3)
C9—N1—C8—O2	4.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.86	1.94	2.622 (4)	135
N2—H2A···O4	0.86	2.57	2.908 (4)	105
C10—H10A···S1	0.97	2.66	3.066 (5)	105
O3—H3···S1^i	0.82	2.32	3.126 (3)	169
N1—H1A···O4^ii	0.86	2.26	3.113 (4)	170
C1—H1B···O4^ii	0.93	2.28	3.155 (6)	156

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