1-[1-(4-Methoxy­phen­yl)ethyl­idene]-4-phenyl­thio­semicarbazide ethanol hemisolvate

The title compound, C₁₆H₁₇N₃OS·0.5C₂H₆O, was prepared by the reaction of 4-methoxy­acetophenone, hydrazine and phenyl isothio­cyanate. The mol­ecular structure and packing are stabilized by intra­molecular N—H...N and inter­molecular N—H...S and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• H-atom completeness 86%
• Disorder in solvent or counterion
• R factor = 0.092
• wR factor = 0.314
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.314
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       2.62 Sigma
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT084_ALERT_2_C High R2 Value ..................................       0.31
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.83
PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent .........          1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C17
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      40.00 Perc.
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........         O2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C17 H20 N3 O1.5 S1
            Atom count from the _atom_site data:  C17 H17 N3 O1.5 S1
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C17 H20 N3 O1.5 S
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         34.00     34.00    0.00
           H         40.00     34.00    6.00
           N          6.00      6.00    0.00
           O          3.00      3.00    0.00
           S          2.00      2.00    0.00
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-[1-(4-Methoxyphenyl)ethylidene]-4-phenylthiosemicarbazide ethanol hemisolvate

Crystal data

C16H17N3OS·0.5C2H6O	Z = 2
Mr = 322.42	F(000) = 336
Triclinic, P1	Dx = 1.194 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.936 (1) Å	Cell parameters from 25 reflections
b = 11.674 (2) Å	θ = 4–14°
c = 13.962 (3) Å	µ = 0.19 mm^−1
α = 68.50 (3)°	T = 293 K
β = 84.83 (3)°	Block, yellow
γ = 87.53 (3)°	0.35 × 0.25 × 0.25 mm
V = 896.5 (3) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.012
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.6°
Graphite monochromator	h = 0→7
ω scans	k = −13→13
3488 measured reflections	l = −16→16
3152 independent reflections	3 standard reflections every 100 reflections
2151 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.092	H-atom parameters constrained
wR(F^2) = 0.314	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.25	(Δ/σ)max < 0.001
3152 reflections	Δρmax = 1.19 e Å^−3
201 parameters	Δρmin = −0.42 e Å^−3
2 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (16)

Special details

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.94952 (18)	0.12365 (11)	0.58256 (9)	0.0619 (5)
O1	−0.2418 (6)	0.3956 (4)	0.0702 (3)	0.0826 (11)
N1	0.5746 (6)	0.2585 (3)	0.5218 (3)	0.0630 (10)
H1A	0.4635	0.2740	0.4833	0.076*
C1	0.7588 (9)	0.3942 (5)	0.5880 (5)	0.0824 (16)
H1B	0.8903	0.3932	0.5467	0.099*
O2	0.0000	0.0000	0.0000	0.255 (6)*
N2	0.6810 (5)	0.1251 (3)	0.4417 (3)	0.0501 (9)
H2A	0.7610	0.0650	0.4348	0.060*
C2	0.7493 (10)	0.4638 (6)	0.6484 (5)	0.0916 (19)
H2B	0.8764	0.5079	0.6480	0.110*
N3	0.5045 (5)	0.1751 (3)	0.3808 (3)	0.0501 (8)
C3	0.5631 (10)	0.4711 (5)	0.7084 (5)	0.0815 (16)
H3B	0.5572	0.5198	0.7484	0.098*
C4	0.3793 (11)	0.4011 (7)	0.7072 (6)	0.114 (2)
H4A	0.2493	0.4016	0.7495	0.137*
C5	0.3820 (9)	0.3334 (6)	0.6477 (5)	0.0940 (19)
H5A	0.2531	0.2914	0.6467	0.113*
C6	0.5773 (7)	0.3258 (4)	0.5873 (4)	0.0588 (11)
C7	0.7244 (6)	0.1731 (4)	0.5123 (3)	0.0496 (10)
C8	0.4737 (6)	0.1409 (4)	0.3060 (3)	0.0493 (10)
C9	0.6168 (8)	0.0469 (4)	0.2780 (4)	0.0681 (13)
H9A	0.6381	−0.0239	0.3392	0.102*
H9B	0.7612	0.0816	0.2469	0.102*
H9C	0.5427	0.0228	0.2301	0.102*
C10	0.2842 (7)	0.2042 (4)	0.2426 (3)	0.0483 (10)
C11	0.1190 (7)	0.2678 (4)	0.2807 (3)	0.0517 (10)
H11A	0.1246	0.2686	0.3468	0.062*
C12	−0.0539 (7)	0.3302 (4)	0.2215 (3)	0.0592 (11)
H12A	−0.1626	0.3729	0.2479	0.071*
C13	−0.0661 (7)	0.3294 (4)	0.1230 (3)	0.0583 (11)
C14	0.0926 (8)	0.2651 (5)	0.0853 (4)	0.0683 (13)
H14A	0.0853	0.2630	0.0197	0.082*
C15	0.2642 (8)	0.2030 (4)	0.1455 (4)	0.0648 (12)
H15A	0.3702	0.1588	0.1194	0.078*
C16	−0.2723 (11)	0.3942 (6)	−0.0275 (4)	0.098 (2)
H16A	−0.4029	0.4431	−0.0538	0.147*
H16B	−0.2937	0.3111	−0.0223	0.147*
H16C	−0.1411	0.4276	−0.0734	0.147*
C17	0.2291 (19)	−0.034 (2)	0.0154 (17)	0.169 (8)*	0.50
C18	0.195 (5)	−0.108 (3)	0.1300 (18)	0.230 (12)*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0518 (7)	0.0727 (8)	0.0752 (9)	0.0140 (5)	−0.0267 (6)	−0.0400 (6)
O1	0.078 (2)	0.097 (3)	0.076 (2)	0.025 (2)	−0.0353 (18)	−0.0304 (19)
N1	0.054 (2)	0.072 (2)	0.079 (3)	0.0169 (18)	−0.0295 (19)	−0.043 (2)
C1	0.063 (3)	0.088 (4)	0.115 (4)	−0.003 (3)	−0.008 (3)	−0.059 (3)
N2	0.0430 (18)	0.0555 (19)	0.059 (2)	0.0068 (15)	−0.0147 (15)	−0.0277 (16)
C2	0.071 (4)	0.094 (4)	0.141 (5)	0.003 (3)	−0.031 (4)	−0.075 (4)
N3	0.0402 (17)	0.060 (2)	0.0539 (19)	0.0008 (15)	−0.0102 (14)	−0.0240 (16)
C3	0.080 (4)	0.089 (4)	0.102 (4)	0.021 (3)	−0.033 (3)	−0.062 (3)
C4	0.085 (4)	0.140 (6)	0.158 (6)	0.004 (4)	0.009 (4)	−0.106 (6)
C5	0.060 (3)	0.127 (5)	0.136 (5)	−0.004 (3)	−0.010 (3)	−0.095 (4)
C6	0.053 (2)	0.060 (2)	0.073 (3)	0.0149 (19)	−0.025 (2)	−0.032 (2)
C7	0.040 (2)	0.054 (2)	0.058 (2)	−0.0022 (17)	−0.0082 (18)	−0.0236 (19)
C8	0.042 (2)	0.054 (2)	0.056 (2)	−0.0022 (17)	−0.0087 (18)	−0.0241 (19)
C9	0.065 (3)	0.073 (3)	0.085 (3)	0.019 (2)	−0.029 (2)	−0.047 (3)
C10	0.044 (2)	0.049 (2)	0.055 (2)	−0.0041 (17)	−0.0064 (18)	−0.0227 (18)
C11	0.047 (2)	0.061 (2)	0.049 (2)	−0.0036 (18)	−0.0066 (18)	−0.0209 (19)
C12	0.045 (2)	0.064 (3)	0.069 (3)	0.0036 (19)	−0.008 (2)	−0.025 (2)
C13	0.053 (2)	0.062 (3)	0.060 (3)	0.003 (2)	−0.017 (2)	−0.019 (2)
C14	0.074 (3)	0.085 (3)	0.054 (3)	0.009 (3)	−0.023 (2)	−0.032 (2)
C15	0.068 (3)	0.075 (3)	0.061 (3)	0.011 (2)	−0.012 (2)	−0.035 (2)
C16	0.089 (4)	0.128 (5)	0.074 (4)	0.018 (4)	−0.042 (3)	−0.029 (3)

Geometric parameters (Å, º)

S1—C7	1.684 (4)	C5—C6	1.390 (7)
O1—C13	1.371 (5)	C5—H5A	0.9300
O1—C16	1.398 (6)	C8—C10	1.491 (5)
N1—C7	1.342 (5)	C8—C9	1.501 (6)
N1—C6	1.408 (5)	C9—H9A	0.9600
N1—H1A	0.8600	C9—H9B	0.9600
C1—C2	1.366 (7)	C9—H9C	0.9600
C1—C6	1.371 (6)	C10—C15	1.377 (6)
C1—H1B	0.9300	C10—C11	1.389 (6)
O2—C17	1.413 (9)	C11—C12	1.383 (5)
O2—C17^i	1.413 (9)	C11—H11A	0.9300
N2—C7	1.347 (5)	C12—C13	1.387 (6)
N2—N3	1.381 (4)	C12—H12A	0.9300
N2—H2A	0.8600	C13—C14	1.366 (6)
C2—C3	1.345 (8)	C14—C15	1.383 (6)
C2—H2B	0.9300	C14—H14A	0.9300
N3—C8	1.277 (5)	C15—H15A	0.9300
C3—C4	1.396 (9)	C16—H16A	0.9600
C3—H3B	0.9300	C16—H16B	0.9600
C4—C5	1.339 (8)	C16—H16C	0.9600
C4—H4A	0.9300	C17—C18	1.513 (10)
C13—O1—C16	119.2 (4)	C10—C8—C9	120.0 (3)
C7—N1—C6	127.8 (3)	C8—C9—H9A	109.5
C7—N1—H1A	116.1	C8—C9—H9B	109.5
C6—N1—H1A	116.1	H9A—C9—H9B	109.5
C2—C1—C6	120.9 (5)	C8—C9—H9C	109.5
C2—C1—H1B	119.5	H9A—C9—H9C	109.5
C6—C1—H1B	119.5	H9B—C9—H9C	109.5
C17—O2—C17^i	180.0 (18)	C15—C10—C11	117.2 (4)
C7—N2—N3	118.1 (3)	C15—C10—C8	122.6 (4)
C7—N2—H2A	120.9	C11—C10—C8	120.2 (4)
N3—N2—H2A	120.9	C12—C11—C10	120.8 (4)
C3—C2—C1	122.5 (5)	C12—C11—H11A	119.6
C3—C2—H2B	118.7	C10—C11—H11A	119.6
C1—C2—H2B	118.7	C11—C12—C13	120.4 (4)
C8—N3—N2	119.7 (3)	C11—C12—H12A	119.8
C2—C3—C4	116.1 (5)	C13—C12—H12A	119.8
C2—C3—H3B	122.0	C14—C13—O1	124.8 (4)
C4—C3—H3B	122.0	C14—C13—C12	119.4 (4)
C5—C4—C3	122.9 (6)	O1—C13—C12	115.8 (4)
C5—C4—H4A	118.6	C13—C14—C15	119.5 (4)
C3—C4—H4A	118.6	C13—C14—H14A	120.2
C4—C5—C6	120.1 (5)	C15—C14—H14A	120.2
C4—C5—H5A	120.0	C10—C15—C14	122.6 (4)
C6—C5—H5A	120.0	C10—C15—H15A	118.7
C1—C6—C5	117.4 (4)	C14—C15—H15A	118.7
C1—C6—N1	122.9 (4)	O1—C16—H16A	109.5
C5—C6—N1	119.4 (4)	O1—C16—H16B	109.5
N1—C7—N2	114.9 (3)	H16A—C16—H16B	109.5
N1—C7—S1	124.7 (3)	O1—C16—H16C	109.5
N2—C7—S1	120.4 (3)	H16A—C16—H16C	109.5
N3—C8—C10	115.4 (3)	H16B—C16—H16C	109.5
N3—C8—C9	124.6 (4)	O2—C17—C18	96.9 (16)
C6—C1—C2—C3	−1.2 (10)	N3—C8—C10—C15	162.5 (4)
C7—N2—N3—C8	172.6 (4)	C9—C8—C10—C15	−15.7 (6)
C1—C2—C3—C4	1.1 (10)	N3—C8—C10—C11	−17.3 (6)
C2—C3—C4—C5	−2.2 (11)	C9—C8—C10—C11	164.5 (4)
C3—C4—C5—C6	3.2 (12)	C15—C10—C11—C12	−1.9 (6)
C2—C1—C6—C5	2.1 (9)	C8—C10—C11—C12	178.0 (4)
C2—C1—C6—N1	176.2 (5)	C10—C11—C12—C13	0.5 (6)
C4—C5—C6—C1	−3.0 (9)	C16—O1—C13—C14	3.4 (7)
C4—C5—C6—N1	−177.3 (6)	C16—O1—C13—C12	−176.8 (5)
C7—N1—C6—C1	54.7 (7)	C11—C12—C13—C14	0.8 (7)
C7—N1—C6—C5	−131.3 (6)	C11—C12—C13—O1	−179.0 (4)
C6—N1—C7—N2	−178.8 (4)	O1—C13—C14—C15	179.1 (5)
C6—N1—C7—S1	2.4 (7)	C12—C13—C14—C15	−0.7 (7)
N3—N2—C7—N1	5.9 (5)	C11—C10—C15—C14	2.0 (7)
N3—N2—C7—S1	−175.2 (3)	C8—C10—C15—C14	−177.8 (4)
N2—N3—C8—C10	−177.7 (3)	C13—C14—C15—C10	−0.7 (8)
N2—N3—C8—C9	0.5 (6)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3	0.86	2.14	2.566 (5)	110
N2—H2A···S1^ii	0.86	2.80	3.660 (4)	176
C9—H9A···S1^ii	0.96	2.80	3.464 (5)	127

Symmetry code: (ii) −x+2, −y, −z+1.