Crystal structure of 2-benzoyl­amino-N′-(4-hy­droxy­benzyl­idene)-3-(thio­phen-2-yl)prop-2-eno­hydrazide

In the crystal a combination of N—H...O and asymmetric bifurcated O—H...(N,O) hydrogen bonds link the mol­ecules into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.113
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

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Alert level C
PLAT414_ALERT_2_C Short Intra D-H..H-X       H3     ..  H11     ..       1.99 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min)           7 Note

Alert level G
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
   1 ALERT level G = General information/check it is not something unexpected

   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


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Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
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   1 ALERT level A = Data missing that is essential or data in wrong format
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Computing details

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009).

2-Benzoylamino-N'-(4-hydroxybenzylidene)-3-(thiophen-2-yl)prop-2-enohydrazide

Crystal data

C21H17N3O3S	F(000) = 1632
Mr = 391.43	Dx = 1.357 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.5212 (7) Å	Cell parameters from 6327 reflections
b = 10.1879 (4) Å	θ = 3.4–32.0°
c = 17.3592 (5) Å	µ = 0.20 mm^−1
β = 105.801 (3)°	T = 298 K
V = 3832.5 (2) Å^3	Plate, colourless
Z = 8	0.42 × 0.32 × 0.18 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer	3426 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm^-1	Rint = 0.024
φ and ω scans	θmax = 27.6°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −25→29
Tmin = 0.757, Tmax = 0.965	k = −13→7
9963 measured reflections	l = −20→22
4419 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0475P)^2 + 2.5641P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
4419 reflections	Δρmax = 0.24 e Å^−3
262 parameters	Δρmin = −0.26 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
C1	0.53659 (7)	0.43211 (16)	0.64694 (9)	0.0306 (3)
O1	0.56722 (5)	0.47222 (13)	0.71288 (7)	0.0423 (3)
C2	0.47457 (7)	0.48794 (16)	0.60847 (9)	0.0299 (3)
C3	0.43369 (7)	0.43455 (17)	0.54526 (9)	0.0347 (4)
H3	0.4469	0.3586	0.5252	0.042*
N11	0.55560 (6)	0.33591 (15)	0.60668 (8)	0.0348 (3)
H11	0.5363 (9)	0.3157 (19)	0.5583 (12)	0.042*
N12	0.61135 (6)	0.27363 (15)	0.63980 (8)	0.0350 (3)
C17	0.62189 (8)	0.17766 (18)	0.59827 (10)	0.0372 (4)
H17	0.5924	0.1570	0.5509	0.045*
C11	0.67784 (7)	0.09896 (17)	0.62156 (10)	0.0349 (4)
C12	0.72750 (8)	0.13084 (18)	0.68643 (10)	0.0382 (4)
H12	0.7261	0.2068	0.7156	0.046*
C13	0.77876 (8)	0.05097 (19)	0.70785 (10)	0.0393 (4)
H13	0.8115	0.0730	0.7515	0.047*
C14	0.78174 (8)	−0.06236 (18)	0.66441 (10)	0.0373 (4)
O14	0.83122 (6)	−0.14325 (14)	0.68163 (9)	0.0524 (4)
H14	0.8583 (12)	−0.115 (3)	0.7211 (15)	0.079*
C15	0.73300 (8)	−0.09439 (18)	0.59955 (11)	0.0436 (4)
H15	0.7346	−0.1700	0.5701	0.052*
C16	0.68189 (8)	−0.01392 (19)	0.57854 (10)	0.0421 (4)
H16	0.6494	−0.0358	0.5345	0.050*
N21	0.45947 (6)	0.60302 (14)	0.64533 (8)	0.0326 (3)
H21	0.4510 (9)	0.5932 (19)	0.6884 (11)	0.039*
C27	0.46800 (7)	0.72320 (17)	0.61800 (9)	0.0314 (3)
O27	0.49198 (6)	0.73798 (13)	0.56269 (7)	0.0435 (3)
C21	0.44374 (8)	0.83722 (17)	0.65374 (9)	0.0360 (4)
C22	0.40355 (9)	0.8231 (2)	0.70116 (12)	0.0497 (5)
H22	0.3933	0.7395	0.7149	0.060*
C23	0.37867 (11)	0.9317 (3)	0.72807 (14)	0.0642 (6)
H23	0.3519	0.9210	0.7600	0.077*
C24	0.39294 (12)	1.0539 (2)	0.70834 (14)	0.0676 (7)
H24	0.3756	1.1267	0.7263	0.081*
C25	0.43304 (14)	1.0707 (2)	0.66171 (15)	0.0737 (7)
H25	0.4430	1.1548	0.6485	0.088*
C26	0.45857 (11)	0.9615 (2)	0.63441 (12)	0.0551 (5)
H26	0.4857	0.9727	0.6030	0.066*
S31	0.33408 (2)	0.61148 (5)	0.52709 (3)	0.04314 (14)
C32	0.37235 (8)	0.47716 (18)	0.50374 (10)	0.0367 (4)
C33	0.33582 (9)	0.4137 (2)	0.43779 (12)	0.0518 (5)
H33	0.3482	0.3392	0.4153	0.062*
C34	0.27760 (9)	0.4737 (3)	0.40789 (12)	0.0597 (6)
H34	0.2473	0.4425	0.3640	0.072*
C35	0.27068 (9)	0.5808 (2)	0.44974 (12)	0.0533 (5)
H35	0.2353	0.6323	0.4378	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0294 (8)	0.0327 (8)	0.0303 (7)	0.0004 (6)	0.0090 (6)	0.0012 (6)
O1	0.0340 (6)	0.0506 (8)	0.0378 (6)	0.0050 (5)	0.0019 (5)	−0.0115 (6)
C2	0.0310 (8)	0.0298 (8)	0.0301 (7)	0.0047 (6)	0.0107 (6)	0.0002 (6)
C3	0.0330 (8)	0.0346 (9)	0.0370 (8)	0.0039 (7)	0.0103 (7)	−0.0042 (7)
N11	0.0316 (7)	0.0407 (8)	0.0293 (6)	0.0108 (6)	0.0037 (6)	−0.0008 (6)
N12	0.0307 (7)	0.0406 (8)	0.0335 (7)	0.0096 (6)	0.0086 (6)	0.0043 (6)
C17	0.0346 (8)	0.0429 (10)	0.0323 (8)	0.0077 (7)	0.0062 (7)	0.0036 (7)
C11	0.0338 (8)	0.0383 (9)	0.0330 (8)	0.0069 (7)	0.0097 (7)	0.0043 (7)
C12	0.0378 (9)	0.0399 (10)	0.0368 (8)	0.0055 (7)	0.0103 (7)	−0.0036 (7)
C13	0.0332 (8)	0.0485 (11)	0.0335 (8)	0.0033 (8)	0.0047 (7)	0.0003 (8)
C14	0.0337 (8)	0.0367 (9)	0.0401 (9)	0.0080 (7)	0.0078 (7)	0.0092 (7)
O14	0.0425 (7)	0.0490 (8)	0.0558 (8)	0.0182 (6)	−0.0034 (6)	−0.0021 (7)
C15	0.0417 (10)	0.0354 (10)	0.0488 (10)	0.0076 (8)	0.0043 (8)	−0.0061 (8)
C16	0.0360 (9)	0.0439 (11)	0.0402 (9)	0.0058 (8)	0.0000 (7)	−0.0040 (8)
N21	0.0376 (7)	0.0343 (8)	0.0279 (6)	0.0073 (6)	0.0123 (6)	−0.0011 (6)
C27	0.0296 (8)	0.0349 (9)	0.0266 (7)	0.0033 (6)	0.0023 (6)	−0.0035 (6)
O27	0.0537 (8)	0.0439 (8)	0.0375 (6)	−0.0012 (6)	0.0203 (6)	−0.0028 (5)
C21	0.0363 (9)	0.0357 (9)	0.0305 (8)	0.0061 (7)	−0.0002 (7)	−0.0061 (7)
C22	0.0499 (11)	0.0483 (12)	0.0534 (11)	0.0079 (9)	0.0185 (9)	−0.0102 (9)
C23	0.0613 (14)	0.0656 (16)	0.0688 (14)	0.0177 (12)	0.0231 (11)	−0.0200 (12)
C24	0.0798 (17)	0.0531 (14)	0.0641 (14)	0.0248 (12)	0.0095 (12)	−0.0189 (11)
C25	0.108 (2)	0.0359 (12)	0.0719 (15)	0.0058 (13)	0.0156 (15)	−0.0041 (11)
C26	0.0741 (15)	0.0385 (11)	0.0527 (11)	0.0012 (10)	0.0175 (11)	−0.0040 (9)
S31	0.0342 (2)	0.0489 (3)	0.0449 (3)	0.00813 (19)	0.00828 (18)	−0.0011 (2)
C32	0.0326 (8)	0.0431 (10)	0.0338 (8)	0.0015 (7)	0.0080 (7)	−0.0027 (7)
C33	0.0381 (10)	0.0649 (14)	0.0475 (10)	0.0022 (9)	0.0034 (8)	−0.0158 (9)
C34	0.0363 (10)	0.0921 (18)	0.0430 (10)	0.0006 (11)	−0.0025 (8)	−0.0101 (11)
C35	0.0328 (9)	0.0762 (15)	0.0471 (11)	0.0103 (9)	0.0047 (8)	0.0074 (10)

Geometric parameters (Å, º)

C1—O1	1.2342 (19)	N21—C27	1.346 (2)
C1—N11	1.340 (2)	N21—H21	0.826 (19)
C1—C2	1.487 (2)	C27—O27	1.2322 (19)
C2—C3	1.341 (2)	C27—C21	1.489 (2)
C2—N21	1.421 (2)	C21—C26	1.374 (3)
C3—C32	1.440 (2)	C21—C22	1.387 (3)
C3—H3	0.9300	C22—C23	1.378 (3)
N11—N12	1.3844 (18)	C22—H22	0.9300
N11—H11	0.859 (19)	C23—C24	1.353 (4)
N12—C17	1.275 (2)	C23—H23	0.9300
C17—C11	1.455 (2)	C24—C25	1.378 (4)
C17—H17	0.9300	C24—H24	0.9300
C11—C16	1.388 (2)	C25—C26	1.394 (3)
C11—C12	1.392 (2)	C25—H25	0.9300
C12—C13	1.378 (2)	C26—H26	0.9300
C12—H12	0.9300	S31—C35	1.702 (2)
C13—C14	1.391 (3)	S31—C32	1.7235 (18)
C13—H13	0.9300	C32—C33	1.376 (2)
C14—O14	1.352 (2)	C33—C34	1.411 (3)
C14—C15	1.381 (2)	C33—H33	0.9300
O14—H14	0.84 (3)	C34—C35	1.343 (3)
C15—C16	1.379 (2)	C34—H34	0.9300
C15—H15	0.9300	C35—H35	0.9300
C16—H16	0.9300
O1—C1—N11	123.27 (15)	C27—N21—H21	121.3 (14)
O1—C1—C2	120.61 (15)	C2—N21—H21	116.8 (14)
N11—C1—C2	116.11 (13)	O27—C27—N21	121.39 (15)
C3—C2—N21	120.54 (14)	O27—C27—C21	121.18 (16)
C3—C2—C1	124.32 (15)	N21—C27—C21	117.32 (14)
N21—C2—C1	115.10 (13)	C26—C21—C22	118.82 (18)
C2—C3—C32	129.69 (16)	C26—C21—C27	118.41 (17)
C2—C3—H3	115.2	C22—C21—C27	122.62 (17)
C32—C3—H3	115.2	C23—C22—C21	120.6 (2)
C1—N11—N12	120.08 (13)	C23—C22—H22	119.7
C1—N11—H11	122.5 (13)	C21—C22—H22	119.7
N12—N11—H11	117.2 (13)	C24—C23—C22	120.5 (2)
C17—N12—N11	113.83 (14)	C24—C23—H23	119.8
N12—C17—C11	123.09 (15)	C22—C23—H23	119.8
N12—C17—H17	118.5	C23—C24—C25	120.1 (2)
C11—C17—H17	118.5	C23—C24—H24	119.9
C16—C11—C12	118.20 (15)	C25—C24—H24	119.9
C16—C11—C17	119.08 (15)	C24—C25—C26	119.9 (2)
C12—C11—C17	122.71 (16)	C24—C25—H25	120.1
C13—C12—C11	120.66 (17)	C26—C25—H25	120.1
C13—C12—H12	119.7	C21—C26—C25	120.2 (2)
C11—C12—H12	119.7	C21—C26—H26	119.9
C12—C13—C14	120.29 (16)	C25—C26—H26	119.9
C12—C13—H13	119.9	C35—S31—C32	91.97 (10)
C14—C13—H13	119.9	C33—C32—C3	123.35 (17)
O14—C14—C15	117.42 (17)	C33—C32—S31	110.17 (14)
O14—C14—C13	123.00 (16)	C3—C32—S31	126.48 (13)
C15—C14—C13	119.57 (15)	C32—C33—C34	112.82 (19)
C14—O14—H14	110.1 (19)	C32—C33—H33	123.6
C16—C15—C14	119.75 (17)	C34—C33—H33	123.6
C16—C15—H15	120.1	C35—C34—C33	112.70 (18)
C14—C15—H15	120.1	C35—C34—H34	123.7
C15—C16—C11	121.52 (16)	C33—C34—H34	123.7
C15—C16—H16	119.2	C34—C35—S31	112.35 (15)
C11—C16—H16	119.2	C34—C35—H35	123.8
C27—N21—C2	121.16 (13)	S31—C35—H35	123.8
O1—C1—C2—C3	−166.88 (16)	C2—N21—C27—O27	−3.6 (2)
N11—C1—C2—C3	11.8 (2)	C2—N21—C27—C21	172.62 (13)
O1—C1—C2—N21	11.0 (2)	O27—C27—C21—C26	−11.9 (2)
N11—C1—C2—N21	−170.33 (14)	N21—C27—C21—C26	171.89 (16)
N21—C2—C3—C32	1.0 (3)	O27—C27—C21—C22	163.63 (16)
C1—C2—C3—C32	178.77 (16)	N21—C27—C21—C22	−12.6 (2)
O1—C1—N11—N12	1.9 (3)	C26—C21—C22—C23	0.3 (3)
C2—C1—N11—N12	−176.74 (14)	C27—C21—C22—C23	−175.14 (17)
C1—N11—N12—C17	175.03 (16)	C21—C22—C23—C24	0.3 (3)
N11—N12—C17—C11	179.60 (16)	C22—C23—C24—C25	−0.6 (4)
N12—C17—C11—C16	171.54 (17)	C23—C24—C25—C26	0.4 (4)
N12—C17—C11—C12	−7.3 (3)	C22—C21—C26—C25	−0.5 (3)
C16—C11—C12—C13	−1.0 (3)	C27—C21—C26—C25	175.14 (18)
C17—C11—C12—C13	177.86 (16)	C24—C25—C26—C21	0.1 (4)
C11—C12—C13—C14	0.5 (3)	C2—C3—C32—C33	178.32 (19)
C12—C13—C14—O14	178.76 (17)	C2—C3—C32—S31	−1.3 (3)
C12—C13—C14—C15	0.1 (3)	C35—S31—C32—C33	0.22 (16)
O14—C14—C15—C16	−178.83 (17)	C35—S31—C32—C3	179.89 (17)
C13—C14—C15—C16	−0.1 (3)	C3—C32—C33—C34	179.77 (18)
C14—C15—C16—C11	−0.5 (3)	S31—C32—C33—C34	−0.6 (2)
C12—C11—C16—C15	1.0 (3)	C32—C33—C34—C35	0.7 (3)
C17—C11—C16—C15	−177.89 (18)	C33—C34—C35—S31	−0.5 (3)
C3—C2—N21—C27	−86.1 (2)	C32—S31—C35—C34	0.18 (18)
C1—C2—N21—C27	95.92 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O27^i	0.86 (2)	2.10 (2)	2.9400 (18)	168 (2)
N21—H21···O1^ii	0.827 (19)	2.238 (19)	3.0002 (18)	153.5 (18)
O14—H14···O1^iii	0.84 (3)	1.97 (3)	2.7727 (19)	162 (3)
O14—H14···N12^iii	0.84 (3)	2.59 (3)	3.133 (2)	124 (2)
C3—H3···O27^i	0.93	2.52	3.333 (2)	147
C17—H17···O27^i	0.93	2.57	3.350 (2)	142
C24—H24···O14^iv	0.93	2.58	3.364 (3)	142

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