N′-(4-Methyl­benzyl­idene)thio­phene-2-carbohydrazide

In the title compound, C₁₃H₁₂N₂OS, the dihedral angle between the aromatic rings is 14.84 (17)°. In the crystal, inversion dimers linked by pairs of N—H...O hydrogen bonds generate R₂²(8) loops.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.080
• wR factor = 0.275
• Data-to-parameter ratio = 17.5

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   0.275
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT084_ALERT_2_C High wR2 Value .................................       0.28
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     --  C10     ..       5.04 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    --  C12     ..       6.40 su
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..          5
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          4
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         56
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600          9

Alert level G
PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large.       0.17
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C1

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

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


checkCIF publication errors

Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 130
              pairs of N---H...O hydrogen bonds generate <i>R</i>~2~^2~(8) loops.
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~
PUBL023_ALERT_1_A There is a mismatched ^ on line 130
              pairs of N---H...O hydrogen bonds generate <i>R</i>~2~^2~(8) loops.
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C

Alert level G
PUBL013_ALERT_1_G The _publ_section_comment (discussion of study) is
            missing. This is required for a full paper submission (but is
            optional for an electronic paper).

   2 ALERT level A = Data missing that is essential or data in wrong format
   1 ALERT level G = General alerts. Data that may be required is missing

---

Related literature

For a related structure, see: Li & Jian (2010).

S1. Experimental

A mixture of thiophene-2-carbohydrazide (0.10 mol) and 4-methylbenzaldehyde (0.10 mol) was stirred in refluxing ethanol (10 ml) for 4 h to afford the title compound (0.079 mol, yield 79%). Colourless blocks of (I) were obtained by recrystallization from ethanol at room temperature.

S2. Refinement

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances = 0.93-0.97 Å; N—H = 0.86Å and with U_iso(H) = 1.2U_eq(C,N) or 1.5U_eq(C_methyl).

Structure description

For a related structure, see: Li & Jian (2010).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

Fig. 1. The structure of (I) showing 30% probability displacement ellipsoids.

N'-(4-Methylbenzylidene)thiophene-2-carbohydrazide

Crystal data

C13H12N2OS	F(000) = 512
Mr = 244.31	Dx = 1.340 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1759 reflections
a = 14.920 (3) Å	θ = 27.5–3.4°
b = 5.3976 (11) Å	µ = 0.25 mm^−1
c = 15.636 (3) Å	T = 293 K
β = 105.87 (3)°	Block, colorless
V = 1211.2 (4) Å^3	0.22 × 0.20 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	1759 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.051
Graphite monochromator	θmax = 27.5°, θmin = 3.4°
phi and ω scans	h = −19→19
10416 measured reflections	k = −6→6
2697 independent reflections	l = −20→20

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.275	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.1685P)^2 + 0.1567P] where P = (Fo^2 + 2Fc^2)/3
2697 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.73 e Å^−3
0 restraints	Δρmin = −0.47 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.

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
S1	0.20737 (7)	0.6743 (2)	0.48624 (6)	0.0649 (4)
N1	0.17714 (18)	0.2992 (5)	0.59639 (17)	0.0481 (7)
N2	0.09655 (17)	0.2160 (6)	0.53950 (16)	0.0507 (7)
H2A	0.0658	0.1007	0.5569	0.061*
O1	−0.00815 (15)	0.2169 (5)	0.40660 (15)	0.0576 (7)
C9	0.0635 (2)	0.3089 (6)	0.4567 (2)	0.0461 (7)
C8	0.2059 (2)	0.1867 (6)	0.6707 (2)	0.0506 (8)
H8A	0.1713	0.0564	0.6841	0.061*
C5	0.2924 (2)	0.2600 (6)	0.7348 (2)	0.0476 (7)
C10	0.11121 (19)	0.5146 (6)	0.42646 (19)	0.0460 (7)
C2	0.4649 (2)	0.3822 (8)	0.8565 (2)	0.0573 (9)
C12	0.1361 (2)	0.8109 (7)	0.3262 (2)	0.0607 (10)
H12A	0.1276	0.9021	0.2741	0.073*
C7	0.4251 (2)	0.5308 (8)	0.7826 (2)	0.0636 (10)
H7A	0.4562	0.6732	0.7732	0.076*
C11	0.0757 (2)	0.6016 (6)	0.3332 (2)	0.0506 (8)
H11A	0.0261	0.5375	0.2889	0.061*
C3	0.4150 (3)	0.1770 (7)	0.8695 (2)	0.0665 (10)
H3A	0.4388	0.0766	0.9188	0.080*
C6	0.3420 (3)	0.4727 (8)	0.7240 (2)	0.0598 (9)
H6A	0.3176	0.5765	0.6758	0.072*
C4	0.3296 (3)	0.1174 (8)	0.8101 (2)	0.0631 (10)
H4A	0.2969	−0.0203	0.8211	0.076*
C13	0.2054 (2)	0.8631 (7)	0.4008 (2)	0.0582 (9)
H13A	0.2477	0.9916	0.4041	0.070*
C1	0.5603 (3)	0.4412 (11)	0.9168 (2)	0.0842 (14)
H1B	0.5764	0.3217	0.9640	0.126*
H1C	0.5598	0.6038	0.9415	0.126*
H1D	0.6054	0.4355	0.8833	0.126*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0703 (7)	0.0624 (8)	0.0608 (6)	−0.0180 (4)	0.0157 (5)	−0.0037 (4)
N1	0.0482 (14)	0.0436 (16)	0.0523 (14)	−0.0058 (11)	0.0134 (11)	−0.0062 (12)
N2	0.0476 (14)	0.0518 (18)	0.0515 (15)	−0.0119 (12)	0.0119 (11)	−0.0025 (12)
O1	0.0464 (12)	0.0575 (16)	0.0636 (14)	−0.0100 (10)	0.0059 (10)	−0.0006 (12)
C9	0.0418 (15)	0.0428 (19)	0.0553 (18)	−0.0020 (12)	0.0160 (13)	−0.0049 (13)
C8	0.0563 (18)	0.049 (2)	0.0486 (17)	−0.0078 (14)	0.0182 (13)	−0.0002 (14)
C5	0.0579 (18)	0.0424 (19)	0.0443 (15)	−0.0017 (14)	0.0170 (13)	−0.0032 (13)
C10	0.0402 (15)	0.0450 (19)	0.0521 (16)	0.0006 (12)	0.0114 (12)	−0.0028 (13)
C2	0.0542 (18)	0.071 (3)	0.0485 (17)	0.0056 (16)	0.0169 (14)	−0.0091 (16)
C12	0.0487 (18)	0.067 (3)	0.067 (2)	0.0068 (15)	0.0157 (15)	0.0172 (18)
C7	0.063 (2)	0.070 (3)	0.0566 (19)	−0.0181 (18)	0.0147 (15)	−0.0001 (18)
C11	0.0444 (16)	0.048 (2)	0.0649 (19)	0.0041 (13)	0.0249 (14)	0.0159 (15)
C3	0.077 (2)	0.063 (3)	0.052 (2)	0.0041 (19)	0.0038 (16)	0.0088 (17)
C6	0.069 (2)	0.055 (2)	0.0504 (17)	−0.0126 (17)	0.0085 (15)	0.0067 (16)
C4	0.078 (2)	0.053 (2)	0.057 (2)	−0.0079 (18)	0.0159 (17)	0.0089 (16)
C13	0.062 (2)	0.046 (2)	0.065 (2)	−0.0056 (15)	0.0150 (16)	0.0037 (16)
C1	0.058 (2)	0.131 (5)	0.059 (2)	0.001 (2)	0.0076 (17)	−0.013 (3)

Geometric parameters (Å, º)

S1—C13	1.673 (3)	C2—C1	1.511 (5)
S1—C10	1.715 (3)	C12—C13	1.360 (5)
N1—C8	1.277 (4)	C12—C11	1.468 (5)
N1—N2	1.362 (3)	C12—H12A	0.9300
N2—C9	1.350 (4)	C7—C6	1.362 (5)
N2—H2A	0.8600	C7—H7A	0.9300
O1—C9	1.242 (4)	C11—H11A	0.9300
C9—C10	1.465 (4)	C3—C4	1.394 (5)
C8—C5	1.455 (4)	C3—H3A	0.9300
C8—H8A	0.9300	C6—H6A	0.9300
C5—C4	1.389 (5)	C4—H4A	0.9300
C5—C6	1.400 (5)	C13—H13A	0.9300
C10—C11	1.486 (4)	C1—H1B	0.9600
C2—C3	1.380 (5)	C1—H1C	0.9600
C2—C7	1.399 (5)	C1—H1D	0.9600
C13—S1—C10	92.39 (16)	C6—C7—H7A	119.1
C8—N1—N2	117.1 (3)	C2—C7—H7A	119.1
C9—N2—N1	122.0 (3)	C12—C11—C10	104.7 (3)
C9—N2—H2A	119.0	C12—C11—H11A	127.6
N1—N2—H2A	119.0	C10—C11—H11A	127.6
O1—C9—N2	118.8 (3)	C2—C3—C4	121.3 (3)
O1—C9—C10	120.7 (3)	C2—C3—H3A	119.4
N2—C9—C10	120.5 (3)	C4—C3—H3A	119.4
N1—C8—C5	120.8 (3)	C7—C6—C5	121.5 (3)
N1—C8—H8A	119.6	C7—C6—H6A	119.3
C5—C8—H8A	119.6	C5—C6—H6A	119.3
C4—C5—C6	117.0 (3)	C5—C4—C3	121.2 (4)
C4—C5—C8	120.4 (3)	C5—C4—H4A	119.4
C6—C5—C8	122.6 (3)	C3—C4—H4A	119.4
C9—C10—C11	118.8 (3)	C12—C13—S1	113.7 (3)
C9—C10—S1	127.8 (2)	C12—C13—H13A	123.1
C11—C10—S1	113.4 (2)	S1—C13—H13A	123.1
C3—C2—C7	117.2 (3)	C2—C1—H1B	109.5
C3—C2—C1	122.1 (4)	C2—C1—H1C	109.5
C7—C2—C1	120.6 (4)	H1B—C1—H1C	109.5
C13—C12—C11	115.7 (3)	C2—C1—H1D	109.5
C13—C12—H12A	122.1	H1B—C1—H1D	109.5
C11—C12—H12A	122.1	H1C—C1—H1D	109.5
C6—C7—C2	121.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1^i	0.86	2.07	2.919 (4)	170

Symmetry code: (i) −x, −y, −z+1.