A non-solvated form of [(Z)-O-methyl-N-(2-methyl­phen­yl)­thio­carbamato-κS](tri­phenyl­phosphane-κP)gold(I): crystal structure and Hirshfeld surface analysis

A near linear geometry for the gold(I) atom defined by a P, S donor set is found in the title compound; an intra­molecular Au...O short contact is noted. Supra­molecular layers sustained by C—H...π and π—π inter­actions feature in the crystal.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.023
• wR factor = 0.055
• Data-to-parameter ratio = 24.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........         --
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         12 Report

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C27 H25 Au1 N1 O1 P1 S1
            Atom count from _chemical_formula_moiety:
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        207 Note
PLAT933_ALERT_2_G Number of OMIT records in Embedded RES .........         14 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           9 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   4 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
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001), DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

[(Z)-O-Methyl-N-(2-methylphenyl)thiocarbamato-κS](triphenylphosphane-κP)gold(I)

Crystal data

[Au(C9H10NOS)(C18H15P)]	Z = 2
Mr = 639.47	F(000) = 624
Triclinic, P1	Dx = 1.767 Mg m^−3
a = 9.3884 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0610 (8) Å	Cell parameters from 9945 reflections
c = 13.3572 (11) Å	θ = 2.3–30.6°
α = 96.194 (1)°	µ = 6.30 mm^−1
β = 102.487 (1)°	T = 100 K
γ = 99.443 (1)°	Block, colourless
V = 1201.60 (17) Å^3	0.30 × 0.11 × 0.09 mm

Data collection

Bruker SMART APEX CCD diffractometer	7189 independent reflections
Radiation source: fine-focus sealed tube	6714 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 30.6°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.368, Tmax = 0.746	k = −14→14
18394 measured reflections	l = −18→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.023	H-atom parameters constrained
wR(F^2) = 0.055	w = 1/[σ^2(Fo^2) + (0.0186P)^2 + 1.2573P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
7189 reflections	Δρmax = 0.97 e Å^−3
291 parameters	Δρmin = −1.14 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Au	0.62037 (2)	0.84221 (2)	0.31176 (2)	0.01464 (3)
S1	0.47523 (7)	0.98235 (6)	0.23056 (5)	0.01606 (12)
P1	0.76792 (7)	0.70692 (7)	0.38621 (5)	0.01288 (12)
O1	0.3113 (2)	0.73724 (19)	0.17215 (15)	0.0192 (4)
N1	0.2275 (3)	0.8941 (2)	0.07556 (17)	0.0173 (4)
C1	0.3230 (3)	0.8657 (3)	0.1480 (2)	0.0155 (5)
C2	0.2349 (3)	1.0288 (3)	0.05179 (19)	0.0142 (5)
C3	0.1468 (3)	1.1117 (3)	0.09059 (19)	0.0146 (5)
C4	0.1448 (3)	1.2394 (3)	0.0581 (2)	0.0171 (5)
H4	0.0852	1.2966	0.0834	0.020*
C5	0.2279 (3)	1.2843 (3)	−0.0102 (2)	0.0189 (5)
H5	0.2256	1.3714	−0.0312	0.023*
C6	0.3149 (3)	1.2004 (3)	−0.0478 (2)	0.0185 (5)
H6	0.3728	1.2305	−0.0941	0.022*
C7	0.3170 (3)	1.0733 (3)	−0.0176 (2)	0.0171 (5)
H7	0.3751	1.0159	−0.0444	0.021*
C8	0.0546 (3)	1.0623 (3)	0.1631 (2)	0.0197 (5)
H8A	−0.0207	1.1186	0.1661	0.030*
H8B	0.1189	1.0691	0.2325	0.030*
H8C	0.0055	0.9672	0.1379	0.030*
C9	0.1757 (3)	0.6439 (3)	0.1169 (2)	0.0254 (6)
H9A	0.1726	0.5565	0.1432	0.038*
H9B	0.1731	0.6299	0.0427	0.038*
H9C	0.0897	0.6822	0.1275	0.038*
C10	0.7737 (3)	0.5607 (3)	0.29563 (19)	0.0141 (4)
C11	0.8969 (3)	0.4975 (3)	0.3086 (2)	0.0188 (5)
H11	0.9803	0.5322	0.3650	0.023*
C12	0.8984 (4)	0.3844 (3)	0.2396 (2)	0.0227 (6)
H12	0.9836	0.3435	0.2477	0.027*
C13	0.7749 (4)	0.3316 (3)	0.1588 (2)	0.0248 (6)
H13	0.7743	0.2522	0.1131	0.030*
C14	0.6526 (4)	0.3940 (3)	0.1447 (2)	0.0274 (6)
H14	0.5689	0.3581	0.0887	0.033*
C15	0.6521 (3)	0.5091 (3)	0.2123 (2)	0.0202 (5)
H15	0.5687	0.5527	0.2016	0.024*
C16	0.9625 (3)	0.7857 (2)	0.4343 (2)	0.0157 (5)
C17	1.0410 (3)	0.7831 (3)	0.5353 (2)	0.0185 (5)
H17	0.9900	0.7481	0.5839	0.022*
C18	1.1938 (3)	0.8315 (3)	0.5651 (2)	0.0211 (5)
H18	1.2467	0.8307	0.6342	0.025*
C19	1.2689 (3)	0.8808 (3)	0.4942 (2)	0.0217 (5)
H19	1.3737	0.9109	0.5140	0.026*
C20	1.1911 (3)	0.8863 (3)	0.3940 (2)	0.0232 (6)
H20	1.2426	0.9221	0.3459	0.028*
C21	1.0389 (3)	0.8399 (3)	0.3643 (2)	0.0200 (5)
H21	0.9860	0.8447	0.2961	0.024*
C22	0.7133 (3)	0.6418 (3)	0.49658 (19)	0.0146 (5)
C23	0.6720 (3)	0.7323 (3)	0.5671 (2)	0.0180 (5)
H23	0.6636	0.8215	0.5527	0.022*
C24	0.6434 (3)	0.6919 (3)	0.6579 (2)	0.0203 (5)
H24	0.6175	0.7540	0.7066	0.024*
C25	0.6526 (3)	0.5605 (3)	0.6777 (2)	0.0218 (5)
H25	0.6333	0.5331	0.7401	0.026*
C26	0.6895 (3)	0.4696 (3)	0.6072 (2)	0.0211 (5)
H26	0.6939	0.3795	0.6209	0.025*
C27	0.7205 (3)	0.5091 (3)	0.5160 (2)	0.0166 (5)
H27	0.7461	0.4465	0.4676	0.020*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au	0.01482 (5)	0.01725 (5)	0.01246 (5)	0.00688 (3)	0.00122 (3)	0.00319 (3)
S1	0.0148 (3)	0.0158 (3)	0.0163 (3)	0.0049 (2)	−0.0005 (2)	0.0021 (2)
P1	0.0130 (3)	0.0143 (3)	0.0110 (3)	0.0041 (2)	0.0010 (2)	0.0018 (2)
O1	0.0209 (10)	0.0144 (9)	0.0202 (9)	0.0052 (7)	−0.0014 (8)	0.0038 (7)
N1	0.0172 (11)	0.0163 (10)	0.0164 (10)	0.0045 (8)	−0.0009 (8)	0.0019 (8)
C1	0.0175 (12)	0.0149 (11)	0.0136 (11)	0.0054 (9)	0.0019 (9)	−0.0005 (9)
C2	0.0130 (11)	0.0151 (11)	0.0114 (10)	0.0026 (9)	−0.0029 (9)	0.0008 (9)
C3	0.0145 (11)	0.0173 (11)	0.0096 (10)	0.0018 (9)	−0.0002 (9)	−0.0004 (9)
C4	0.0205 (13)	0.0151 (11)	0.0153 (11)	0.0051 (10)	0.0027 (10)	0.0017 (9)
C5	0.0212 (13)	0.0167 (12)	0.0174 (12)	0.0006 (10)	0.0027 (10)	0.0046 (10)
C6	0.0173 (12)	0.0225 (13)	0.0159 (12)	0.0019 (10)	0.0051 (10)	0.0038 (10)
C7	0.0135 (11)	0.0202 (12)	0.0166 (12)	0.0048 (10)	0.0011 (9)	0.0006 (10)
C8	0.0215 (13)	0.0206 (12)	0.0159 (12)	0.0016 (10)	0.0040 (10)	0.0021 (10)
C9	0.0283 (15)	0.0145 (12)	0.0278 (15)	−0.0001 (11)	−0.0035 (12)	0.0067 (11)
C10	0.0150 (11)	0.0165 (11)	0.0110 (10)	0.0025 (9)	0.0036 (9)	0.0021 (9)
C11	0.0203 (13)	0.0209 (12)	0.0153 (12)	0.0076 (10)	0.0029 (10)	0.0005 (10)
C12	0.0295 (15)	0.0221 (13)	0.0215 (13)	0.0125 (12)	0.0106 (12)	0.0045 (11)
C13	0.0360 (17)	0.0183 (13)	0.0184 (13)	0.0025 (12)	0.0077 (12)	−0.0037 (10)
C14	0.0290 (16)	0.0279 (15)	0.0175 (13)	−0.0040 (12)	0.0000 (12)	−0.0049 (11)
C15	0.0139 (12)	0.0267 (14)	0.0183 (12)	0.0014 (10)	0.0026 (10)	0.0026 (10)
C16	0.0189 (12)	0.0112 (10)	0.0151 (11)	0.0038 (9)	0.0003 (10)	−0.0004 (9)
C17	0.0174 (12)	0.0191 (12)	0.0173 (12)	0.0018 (10)	0.0020 (10)	0.0027 (10)
C18	0.0157 (12)	0.0208 (13)	0.0214 (13)	−0.0006 (10)	−0.0036 (10)	0.0022 (10)
C19	0.0147 (12)	0.0192 (12)	0.0276 (14)	−0.0016 (10)	0.0039 (11)	−0.0027 (11)
C20	0.0238 (14)	0.0206 (13)	0.0256 (14)	−0.0014 (11)	0.0123 (12)	0.0016 (11)
C21	0.0216 (13)	0.0194 (12)	0.0183 (12)	0.0037 (10)	0.0030 (10)	0.0038 (10)
C22	0.0140 (11)	0.0157 (11)	0.0135 (11)	0.0029 (9)	0.0021 (9)	0.0014 (9)
C23	0.0178 (12)	0.0174 (12)	0.0174 (12)	0.0031 (10)	0.0026 (10)	−0.0005 (9)
C24	0.0187 (13)	0.0247 (13)	0.0160 (12)	0.0032 (11)	0.0041 (10)	−0.0014 (10)
C25	0.0176 (13)	0.0326 (15)	0.0160 (12)	0.0038 (11)	0.0051 (10)	0.0062 (11)
C26	0.0217 (13)	0.0199 (13)	0.0237 (14)	0.0038 (10)	0.0077 (11)	0.0066 (10)
C27	0.0167 (12)	0.0162 (11)	0.0166 (12)	0.0051 (9)	0.0025 (10)	0.0014 (9)

Geometric parameters (Å, º)

Au—P1	2.2529 (6)	C11—H11	0.9500
Au—S1	2.3114 (6)	C12—C13	1.387 (4)
S1—C1	1.768 (3)	C12—H12	0.9500
P1—C16	1.812 (3)	C13—C14	1.384 (5)
P1—C22	1.814 (3)	C13—H13	0.9500
P1—C10	1.817 (3)	C14—C15	1.391 (4)
O1—C1	1.359 (3)	C14—H14	0.9500
O1—C9	1.449 (3)	C15—H15	0.9500
N1—C1	1.260 (3)	C16—C17	1.396 (4)
N1—C2	1.419 (3)	C16—C21	1.399 (4)
C2—C7	1.392 (4)	C17—C18	1.391 (4)
C2—C3	1.403 (4)	C17—H17	0.9500
C3—C4	1.402 (4)	C18—C19	1.383 (4)
C3—C8	1.503 (4)	C18—H18	0.9500
C4—C5	1.388 (4)	C19—C20	1.391 (4)
C4—H4	0.9500	C19—H19	0.9500
C5—C6	1.394 (4)	C20—C21	1.384 (4)
C5—H5	0.9500	C20—H20	0.9500
C6—C7	1.383 (4)	C21—H21	0.9500
C6—H6	0.9500	C22—C27	1.396 (4)
C7—H7	0.9500	C22—C23	1.398 (4)
C8—H8A	0.9800	C23—C24	1.386 (4)
C8—H8B	0.9800	C23—H23	0.9500
C8—H8C	0.9800	C24—C25	1.388 (4)
C9—H9A	0.9800	C24—H24	0.9500
C9—H9B	0.9800	C25—C26	1.379 (4)
C9—H9C	0.9800	C25—H25	0.9500
C10—C11	1.396 (4)	C26—C27	1.396 (4)
C10—C15	1.394 (4)	C26—H26	0.9500
C11—C12	1.389 (4)	C27—H27	0.9500
P1—Au—S1	177.61 (2)	C13—C12—C11	119.7 (3)
C1—S1—Au	103.14 (9)	C13—C12—H12	120.2
C16—P1—C22	104.74 (12)	C11—C12—H12	120.2
C16—P1—C10	102.91 (12)	C14—C13—C12	120.2 (3)
C22—P1—C10	107.07 (12)	C14—C13—H13	119.9
C16—P1—Au	115.26 (8)	C12—C13—H13	119.9
C22—P1—Au	113.63 (9)	C13—C14—C15	120.2 (3)
C10—P1—Au	112.28 (9)	C13—C14—H14	119.9
C1—O1—C9	114.9 (2)	C15—C14—H14	119.9
C1—N1—C2	121.4 (2)	C14—C15—C10	120.1 (3)
N1—C1—O1	120.7 (2)	C14—C15—H15	120.0
N1—C1—S1	125.9 (2)	C10—C15—H15	120.0
O1—C1—S1	113.38 (18)	C17—C16—C21	119.2 (3)
C7—C2—C3	120.2 (2)	C17—C16—P1	122.4 (2)
C7—C2—N1	120.3 (2)	C21—C16—P1	118.1 (2)
C3—C2—N1	119.2 (2)	C18—C17—C16	120.2 (3)
C4—C3—C2	118.3 (2)	C18—C17—H17	119.9
C4—C3—C8	121.4 (2)	C16—C17—H17	119.9
C2—C3—C8	120.4 (2)	C19—C18—C17	120.1 (3)
C5—C4—C3	121.5 (2)	C19—C18—H18	120.0
C5—C4—H4	119.3	C17—C18—H18	120.0
C3—C4—H4	119.3	C18—C19—C20	120.1 (3)
C4—C5—C6	119.3 (2)	C18—C19—H19	119.9
C4—C5—H5	120.3	C20—C19—H19	119.9
C6—C5—H5	120.3	C21—C20—C19	120.0 (3)
C7—C6—C5	120.1 (2)	C21—C20—H20	120.0
C7—C6—H6	120.0	C19—C20—H20	120.0
C5—C6—H6	120.0	C20—C21—C16	120.4 (3)
C6—C7—C2	120.6 (2)	C20—C21—H21	119.8
C6—C7—H7	119.7	C16—C21—H21	119.8
C2—C7—H7	119.7	C27—C22—C23	119.9 (2)
C3—C8—H8A	109.5	C27—C22—P1	122.34 (19)
C3—C8—H8B	109.5	C23—C22—P1	117.6 (2)
H8A—C8—H8B	109.5	C24—C23—C22	120.0 (3)
C3—C8—H8C	109.5	C24—C23—H23	120.0
H8A—C8—H8C	109.5	C22—C23—H23	120.0
H8B—C8—H8C	109.5	C25—C24—C23	119.9 (3)
O1—C9—H9A	109.5	C25—C24—H24	120.0
O1—C9—H9B	109.5	C23—C24—H24	120.0
H9A—C9—H9B	109.5	C26—C25—C24	120.4 (3)
O1—C9—H9C	109.5	C26—C25—H25	119.8
H9A—C9—H9C	109.5	C24—C25—H25	119.8
H9B—C9—H9C	109.5	C25—C26—C27	120.5 (3)
C11—C10—C15	119.2 (2)	C25—C26—H26	119.8
C11—C10—P1	121.3 (2)	C27—C26—H26	119.8
C15—C10—P1	119.5 (2)	C22—C27—C26	119.3 (2)
C12—C11—C10	120.6 (3)	C22—C27—H27	120.4
C12—C11—H11	119.7	C26—C27—H27	120.4
C10—C11—H11	119.7
C2—N1—C1—O1	177.6 (2)	C11—C10—C15—C14	1.7 (4)
C2—N1—C1—S1	0.8 (4)	P1—C10—C15—C14	−177.5 (2)
C9—O1—C1—N1	−6.4 (4)	C22—P1—C16—C17	2.7 (2)
C9—O1—C1—S1	170.9 (2)	C10—P1—C16—C17	−109.1 (2)
Au—S1—C1—N1	−167.2 (2)	Au—P1—C16—C17	128.3 (2)
Au—S1—C1—O1	15.8 (2)	C22—P1—C16—C21	176.7 (2)
C1—N1—C2—C7	88.2 (3)	C10—P1—C16—C21	64.9 (2)
C1—N1—C2—C3	−98.3 (3)	Au—P1—C16—C21	−57.6 (2)
C7—C2—C3—C4	−0.4 (4)	C21—C16—C17—C18	−1.2 (4)
N1—C2—C3—C4	−173.9 (2)	P1—C16—C17—C18	172.8 (2)
C7—C2—C3—C8	178.3 (2)	C16—C17—C18—C19	−0.9 (4)
N1—C2—C3—C8	4.7 (4)	C17—C18—C19—C20	2.2 (4)
C2—C3—C4—C5	−0.3 (4)	C18—C19—C20—C21	−1.4 (4)
C8—C3—C4—C5	−178.9 (2)	C19—C20—C21—C16	−0.7 (4)
C3—C4—C5—C6	0.3 (4)	C17—C16—C21—C20	2.0 (4)
C4—C5—C6—C7	0.5 (4)	P1—C16—C21—C20	−172.3 (2)
C5—C6—C7—C2	−1.2 (4)	C16—P1—C22—C27	−92.1 (2)
C3—C2—C7—C6	1.1 (4)	C10—P1—C22—C27	16.8 (3)
N1—C2—C7—C6	174.6 (2)	Au—P1—C22—C27	141.3 (2)
C16—P1—C10—C11	28.4 (2)	C16—P1—C22—C23	83.8 (2)
C22—P1—C10—C11	−81.7 (2)	C10—P1—C22—C23	−167.4 (2)
Au—P1—C10—C11	152.94 (19)	Au—P1—C22—C23	−42.8 (2)
C16—P1—C10—C15	−152.5 (2)	C27—C22—C23—C24	2.3 (4)
C22—P1—C10—C15	97.5 (2)	P1—C22—C23—C24	−173.7 (2)
Au—P1—C10—C15	−27.9 (2)	C22—C23—C24—C25	−1.4 (4)
C15—C10—C11—C12	−0.2 (4)	C23—C24—C25—C26	−0.2 (4)
P1—C10—C11—C12	178.9 (2)	C24—C25—C26—C27	1.0 (4)
C10—C11—C12—C13	−1.8 (4)	C23—C22—C27—C26	−1.5 (4)
C11—C12—C13—C14	2.3 (5)	P1—C22—C27—C26	174.3 (2)
C12—C13—C14—C15	−0.8 (5)	C25—C26—C27—C22	−0.1 (4)
C13—C14—C15—C10	−1.2 (4)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the (C2–C7) and (C22–C27) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8C···Cg1^i	0.98	2.73	3.481 (3)	134
Cg2—–···Cg2^ii	–	–	3.8033 (17)	–

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