2-[3-(4-Methoxy­benzo­yl)thioureido]-3-phenyl­propionic acid methanol solvate

In the title compound, C₁₈H₁₈N₂O₄S·CH₄O, the 4-methoxy­phenyl and benzyl groups make dihedral angles of 7.28 (18) and 57.54 (18)°, respectively, with the central carbonyl­thio­urea group. The crystal structure is stabilized by inter­molecular hydrogen bonds, N—H...O, O—H...O and C—H...O, forming a two-dimensional network parallel to the bc face.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.079
• wR factor = 0.137
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C11    -C16           1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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               3384
           Count of symmetry unique reflns         2000
           Completeness (_total/calc)            169.20%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1384
           Fraction of Friedel pairs measured     0.692
           Are heavy atom types Z>Si present        yes

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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

---

Computing details

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

2-[3-(4-Methoxybenzoyl)thiouredo]-3-phenylpropionic acid methanol solvate

Crystal data

C18H18N2O4S·CH4O	F(000) = 824
Mr = 390.45	Dx = 1.337 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2510 reflections
a = 5.0364 (13) Å	θ = 1.5–25.0°
b = 16.716 (4) Å	µ = 0.20 mm^−1
c = 23.040 (6) Å	T = 298 K
V = 1939.7 (8) Å^3	Block, colourless
Z = 4	0.48 × 0.19 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3384 independent reflections
Radiation source: fine-focus sealed tube	2977 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 83.66 pixels mm^-1	θmax = 25.0°, θmin = 1.5°
ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −16→19
Tmin = 0.910, Tmax = 0.976	l = −27→27
10023 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)] = 0.079	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.137	w = 1/[σ^2(Fo^2) + (0.0389P)^2 + 0.7377P] where P = (Fo^2 + 2Fc^2)/3
S = 1.33	(Δ/σ)max < 0.001
3384 reflections	Δρmax = 0.26 e Å^−3
257 parameters	Δρmin = −0.16 e Å^−3
4 restraints	Absolute structure: Flack (1983), 1384 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (16)

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

	x	y	z	Uiso*/Ueq
S1	0.8931 (3)	0.90101 (8)	0.74717 (5)	0.0627 (4)
O1	−0.3535 (7)	0.57667 (17)	0.61746 (13)	0.0604 (9)
O2	0.4784 (7)	0.85112 (17)	0.57700 (12)	0.0557 (9)
O3	0.6385 (7)	1.07776 (17)	0.67305 (14)	0.0554 (8)
H3B	0.601 (11)	1.1255 (13)	0.684 (2)	0.083*
O4	1.0361 (7)	1.1322 (2)	0.68191 (14)	0.0660 (10)
O5	0.4778 (7)	0.2280 (2)	0.70430 (16)	0.0616 (9)
H5B	0.311 (3)	0.235 (3)	0.703 (2)	0.092*
N1	0.5648 (8)	0.8338 (2)	0.67224 (14)	0.0445 (9)
H1B	0.522 (8)	0.810 (2)	0.7035 (10)	0.053*
N2	0.8200 (7)	0.9371 (2)	0.63672 (15)	0.0453 (9)
H2A	0.744 (8)	0.928 (2)	0.6040 (10)	0.054*
C1	0.1438 (10)	0.7145 (3)	0.67510 (17)	0.0477 (11)
H1A	0.2210	0.7289	0.7102	0.057*
C2	−0.0507 (9)	0.6559 (2)	0.67477 (18)	0.0469 (11)
H2C	−0.1048	0.6319	0.7092	0.056*
C3	−0.1624 (9)	0.6340 (2)	0.62278 (18)	0.0456 (11)
C4	−0.0828 (11)	0.6697 (3)	0.57183 (18)	0.0586 (13)
H4A	−0.1585	0.6545	0.5367	0.070*
C5	0.1083 (11)	0.7275 (3)	0.57343 (17)	0.0533 (12)
H5A	0.1612	0.7513	0.5388	0.064*
C6	0.2265 (9)	0.7521 (2)	0.62495 (17)	0.0405 (10)
C7	0.4308 (9)	0.8156 (2)	0.62157 (18)	0.0402 (10)
C8	0.7571 (9)	0.8923 (2)	0.68187 (17)	0.0417 (10)
C9	1.0083 (9)	1.0022 (2)	0.63981 (17)	0.0436 (10)
H9A	1.1579	0.9840	0.6636	0.052*
C10	1.1180 (10)	1.0222 (3)	0.57917 (17)	0.0525 (12)
H10A	1.2611	1.0606	0.5835	0.063*
H10B	1.1933	0.9739	0.5626	0.063*
C11	0.9185 (8)	1.0556 (2)	0.53714 (16)	0.0410 (10)
C12	0.7936 (12)	1.0076 (3)	0.4971 (2)	0.0615 (15)
H12A	0.8371	0.9536	0.4951	0.074*
C13	0.6036 (13)	1.0385 (4)	0.4597 (2)	0.0802 (18)
H13A	0.5186	1.0053	0.4332	0.096*
C14	0.5424 (12)	1.1177 (4)	0.4622 (2)	0.0805 (17)
H14A	0.4178	1.1392	0.4368	0.097*
C15	0.6635 (13)	1.1651 (3)	0.5016 (2)	0.0740 (17)
H15A	0.6190	1.2190	0.5036	0.089*
C16	0.8494 (11)	1.1351 (3)	0.5384 (2)	0.0599 (13)
H16A	0.9313	1.1690	0.5650	0.072*
C17	0.8980 (9)	1.0772 (3)	0.66795 (17)	0.0437 (10)
C18	−0.4327 (11)	0.5326 (3)	0.6672 (2)	0.0696 (15)
H18A	−0.5679	0.4949	0.6565	0.104*
H18B	−0.5015	0.5687	0.6960	0.104*
H18C	−0.2825	0.5046	0.6828	0.104*
C19	0.5593 (14)	0.2816 (3)	0.6601 (2)	0.092 (2)
H19A	0.4717	0.3321	0.6653	0.138*
H19B	0.5134	0.2599	0.6229	0.138*
H19C	0.7480	0.2891	0.6622	0.138*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0691 (9)	0.0719 (8)	0.0472 (6)	−0.0174 (7)	−0.0095 (7)	−0.0001 (6)
O1	0.063 (2)	0.0544 (18)	0.0637 (19)	−0.0142 (18)	−0.0045 (18)	0.0067 (16)
O2	0.068 (2)	0.0548 (18)	0.0439 (17)	−0.0054 (16)	−0.0056 (16)	0.0114 (15)
O3	0.044 (2)	0.0462 (19)	0.076 (2)	−0.0008 (17)	−0.0010 (17)	−0.0029 (16)
O4	0.053 (2)	0.068 (2)	0.077 (2)	−0.0301 (19)	−0.0078 (18)	−0.0188 (17)
O5	0.047 (2)	0.065 (2)	0.072 (2)	−0.0008 (18)	−0.0045 (19)	0.0007 (17)
N1	0.052 (2)	0.041 (2)	0.0399 (19)	−0.0035 (19)	0.001 (2)	0.0032 (16)
N2	0.045 (2)	0.043 (2)	0.047 (2)	−0.0011 (18)	−0.0093 (18)	0.0019 (17)
C1	0.052 (3)	0.054 (3)	0.037 (2)	0.001 (2)	−0.008 (2)	−0.002 (2)
C2	0.049 (3)	0.053 (3)	0.039 (2)	−0.003 (2)	0.003 (2)	0.008 (2)
C3	0.047 (3)	0.040 (2)	0.049 (2)	0.000 (2)	−0.005 (2)	−0.002 (2)
C4	0.074 (4)	0.059 (3)	0.043 (2)	−0.015 (3)	−0.011 (3)	0.003 (2)
C5	0.072 (3)	0.051 (3)	0.037 (2)	−0.007 (3)	−0.002 (2)	0.007 (2)
C6	0.043 (3)	0.041 (2)	0.037 (2)	0.011 (2)	0.000 (2)	−0.0017 (19)
C7	0.041 (3)	0.036 (2)	0.044 (2)	0.011 (2)	−0.003 (2)	0.0041 (19)
C8	0.041 (3)	0.032 (2)	0.052 (3)	0.008 (2)	0.004 (2)	0.0040 (19)
C9	0.031 (2)	0.047 (2)	0.053 (2)	−0.004 (2)	−0.006 (2)	0.006 (2)
C10	0.042 (3)	0.057 (3)	0.058 (3)	−0.001 (2)	0.008 (2)	0.000 (2)
C11	0.036 (3)	0.048 (2)	0.039 (2)	−0.005 (2)	0.006 (2)	0.0023 (19)
C12	0.080 (5)	0.051 (3)	0.054 (3)	0.001 (3)	0.014 (3)	−0.004 (2)
C13	0.098 (5)	0.087 (4)	0.056 (3)	−0.038 (4)	−0.023 (4)	0.005 (3)
C14	0.075 (4)	0.097 (5)	0.069 (4)	−0.006 (4)	−0.012 (3)	0.033 (3)
C15	0.084 (5)	0.057 (3)	0.081 (4)	0.010 (3)	−0.015 (4)	0.019 (3)
C16	0.073 (4)	0.045 (3)	0.062 (3)	−0.005 (3)	−0.002 (3)	0.006 (2)
C17	0.034 (3)	0.054 (3)	0.043 (2)	−0.009 (2)	−0.004 (2)	0.012 (2)
C18	0.061 (4)	0.062 (3)	0.086 (3)	−0.007 (3)	0.001 (3)	0.015 (3)
C19	0.114 (6)	0.082 (4)	0.080 (4)	0.018 (4)	0.021 (4)	0.000 (3)

Geometric parameters (Å, º)

S1—C8	1.660 (4)	C6—C7	1.480 (6)
O1—C3	1.364 (5)	C9—C17	1.517 (6)
O1—C18	1.419 (5)	C9—C10	1.539 (6)
O2—C7	1.210 (4)	C9—H9A	0.9800
O3—C17	1.312 (5)	C10—C11	1.503 (6)
O3—H3B	0.86 (3)	C10—H10A	0.9700
O4—C17	1.196 (5)	C10—H10B	0.9700
O5—C19	1.417 (6)	C11—C16	1.374 (6)
O5—H5B	0.851 (10)	C11—C12	1.375 (6)
N1—C7	1.382 (5)	C12—C13	1.387 (8)
N1—C8	1.394 (5)	C12—H12A	0.9300
N1—H1B	0.85 (3)	C13—C14	1.361 (7)
N2—C8	1.320 (5)	C13—H13A	0.9300
N2—C9	1.446 (5)	C14—C15	1.351 (7)
N2—H2A	0.86 (3)	C14—H14A	0.9300
C1—C6	1.380 (5)	C15—C16	1.359 (7)
C1—C2	1.385 (6)	C15—H15A	0.9300
C1—H1A	0.9300	C16—H16A	0.9300
C2—C3	1.373 (6)	C18—H18A	0.9600
C2—H2C	0.9300	C18—H18B	0.9600
C3—C4	1.376 (6)	C18—H18C	0.9600
C4—C5	1.365 (7)	C19—H19A	0.9600
C4—H4A	0.9300	C19—H19B	0.9600
C5—C6	1.390 (6)	C19—H19C	0.9600
C5—H5A	0.9300
C3—O1—C18	119.4 (4)	C11—C10—C9	115.2 (4)
C17—O3—H3B	105 (4)	C11—C10—H10A	108.5
C19—O5—H5B	100 (4)	C9—C10—H10A	108.5
C7—N1—C8	128.9 (3)	C11—C10—H10B	108.5
C7—N1—H1B	119 (3)	C9—C10—H10B	108.5
C8—N1—H1B	112 (3)	H10A—C10—H10B	107.5
C8—N2—C9	123.1 (4)	C16—C11—C12	117.6 (4)
C8—N2—H2A	119 (3)	C16—C11—C10	121.0 (4)
C9—N2—H2A	118 (3)	C12—C11—C10	121.4 (4)
C6—C1—C2	122.1 (4)	C11—C12—C13	121.0 (5)
C6—C1—H1A	119.0	C11—C12—H12A	119.5
C2—C1—H1A	119.0	C13—C12—H12A	119.5
C3—C2—C1	118.9 (4)	C14—C13—C12	119.5 (5)
C3—C2—H2C	120.6	C14—C13—H13A	120.2
C1—C2—H2C	120.6	C12—C13—H13A	120.2
O1—C3—C2	123.7 (4)	C15—C14—C13	119.7 (5)
O1—C3—C4	115.7 (4)	C15—C14—H14A	120.1
C2—C3—C4	120.6 (4)	C13—C14—H14A	120.1
C5—C4—C3	119.3 (4)	C14—C15—C16	121.0 (5)
C5—C4—H4A	120.4	C14—C15—H15A	119.5
C3—C4—H4A	120.4	C16—C15—H15A	119.5
C4—C5—C6	122.3 (4)	C15—C16—C11	121.2 (5)
C4—C5—H5A	118.8	C15—C16—H16A	119.4
C6—C5—H5A	118.8	C11—C16—H16A	119.4
C1—C6—C5	116.8 (4)	O4—C17—O3	123.3 (4)
C1—C6—C7	125.5 (4)	O4—C17—C9	122.5 (4)
C5—C6—C7	117.7 (4)	O3—C17—C9	114.1 (4)
O2—C7—N1	120.8 (4)	O1—C18—H18A	109.5
O2—C7—C6	122.3 (4)	O1—C18—H18B	109.5
N1—C7—C6	116.9 (4)	H18A—C18—H18B	109.5
N2—C8—N1	116.1 (4)	O1—C18—H18C	109.5
N2—C8—S1	124.4 (3)	H18A—C18—H18C	109.5
N1—C8—S1	119.5 (3)	H18B—C18—H18C	109.5
N2—C9—C17	113.8 (4)	O5—C19—H19A	109.5
N2—C9—C10	110.8 (3)	O5—C19—H19B	109.5
C17—C9—C10	109.8 (3)	H19A—C19—H19B	109.5
N2—C9—H9A	107.4	O5—C19—H19C	109.5
C17—C9—H9A	107.4	H19A—C19—H19C	109.5
C10—C9—H9A	107.4	H19B—C19—H19C	109.5
C6—C1—C2—C3	0.8 (7)	C7—N1—C8—N2	0.4 (6)
C18—O1—C3—C2	−4.3 (6)	C7—N1—C8—S1	−178.9 (3)
C18—O1—C3—C4	175.3 (4)	C8—N2—C9—C17	−76.7 (5)
C1—C2—C3—O1	179.4 (4)	C8—N2—C9—C10	158.9 (4)
C1—C2—C3—C4	−0.1 (7)	N2—C9—C10—C11	66.2 (5)
O1—C3—C4—C5	−179.8 (4)	C17—C9—C10—C11	−60.3 (5)
C2—C3—C4—C5	−0.3 (7)	C9—C10—C11—C16	81.1 (5)
C3—C4—C5—C6	−0.1 (8)	C9—C10—C11—C12	−97.1 (5)
C2—C1—C6—C5	−1.0 (6)	C16—C11—C12—C13	−0.4 (7)
C2—C1—C6—C7	179.4 (4)	C10—C11—C12—C13	177.9 (5)
C4—C5—C6—C1	0.7 (7)	C11—C12—C13—C14	0.9 (8)
C4—C5—C6—C7	−179.7 (4)	C12—C13—C14—C15	−1.2 (9)
C8—N1—C7—O2	1.8 (7)	C13—C14—C15—C16	1.1 (9)
C8—N1—C7—C6	−177.3 (4)	C14—C15—C16—C11	−0.6 (9)
C1—C6—C7—O2	−173.4 (4)	C12—C11—C16—C15	0.3 (7)
C5—C6—C7—O2	7.0 (6)	C10—C11—C16—C15	−178.1 (5)
C1—C6—C7—N1	5.7 (6)	N2—C9—C17—O4	168.5 (4)
C5—C6—C7—N1	−173.8 (4)	C10—C9—C17—O4	−66.7 (5)
C9—N2—C8—N1	177.7 (4)	N2—C9—C17—O3	−14.5 (5)
C9—N2—C8—S1	−3.0 (6)	C10—C9—C17—O3	110.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.86 (3)	1.96 (4)	2.630 (5)	134 (3)
C5—H5A···O2	0.93	2.47	2.784 (6)	100
C9—H9A···S1	0.98	2.72	3.052 (4)	100
N1—H1B···O5^i	0.85 (3)	2.53 (3)	3.358 (5)	164 (4)
O3—H3B···O5^ii	0.86 (3)	1.88 (3)	2.735 (5)	174 (6)
O5—H5B···O4^iii	0.85 (2)	2.26 (4)	2.789 (5)	121 (4)
C1—H1A···O5^i	0.93	2.49	3.377 (6)	161
C2—H2C···O4^iv	0.93	2.53	3.327 (5)	143
C10—H10B···O2^v	0.97	2.53	3.386 (6)	148
C13—H13A···O1^vi	0.93	2.60	3.488 (7)	160

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