Crystal structure and theoretical study of (2E)-1-[4-hy­droxy-3-(morpholin-4-ylmeth­yl)phen­yl]-3-(thio­phen-2-yl)prop-2-en-1-one

The mol­ecular conformation is stabilized by an intra­molecular O—H...N hydrogen bond. In the crystal, mol­ecules are linked by C—H...O hydrogen bonds, forming wave-like layers. C—H...π inter­actions involving the benzene rings and the methyl­ene hydrogen atoms of the morpholine rings are observed between the layers.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.050
• wR factor = 0.138
• Data-to-parameter ratio = 19.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         S1 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.239 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         14 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.81 mm
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O3             109.3 Degree
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         11 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...         15 Note
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          6 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         14 Info

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

(2E)-1-[4-Hydroxy-3-(morpholin-4-ylmethyl)phenyl]-3-(thiophen-2-yl)prop-2-en-1-one

Crystal data

C18H19NO3S	F(000) = 696
Mr = 329.40	Dx = 1.316 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.4939 (5) Å	Cell parameters from 9868 reflections
b = 18.5548 (10) Å	θ = 2.2–28.4°
c = 9.5068 (5) Å	µ = 0.21 mm^−1
β = 96.788 (3)°	T = 293 K
V = 1662.95 (15) Å^3	Prism, colourless
Z = 4	0.81 × 0.50 × 0.48 mm

Data collection

Bruker APEXII CCD diffractometer	4168 independent reflections
Radiation source: sealed tube	3373 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 28.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
Tmin = 0.882, Tmax = 0.905	k = −24→24
33902 measured reflections	l = −12→12

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.138	w = 1/[σ^2(Fo^2) + (0.0679P)^2 + 0.4859P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
4168 reflections	Δρmax = 0.32 e Å^−3
211 parameters	Δρmin = −0.25 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	0.3316 (2)	−0.02309 (12)	0.2121 (3)	0.0720 (6)
H1	0.235465	−0.019863	0.221873	0.086*
C2	0.3860 (2)	−0.06817 (11)	0.1231 (2)	0.0623 (5)
H2	0.331381	−0.099790	0.063433	0.075*
C3	0.53423 (18)	−0.06285 (9)	0.12897 (19)	0.0522 (4)
H3	0.587701	−0.090438	0.073164	0.063*
C4	0.59198 (16)	−0.01301 (8)	0.22504 (17)	0.0441 (3)
C5	0.74016 (16)	0.00373 (8)	0.25820 (17)	0.0447 (3)
H5	0.802258	−0.022598	0.209531	0.054*
C6	0.79903 (17)	0.05204 (9)	0.34953 (18)	0.0465 (4)
H6	0.741687	0.080254	0.400249	0.056*
C7	0.95402 (16)	0.06168 (8)	0.37183 (17)	0.0433 (3)
C8	1.01520 (15)	0.12698 (8)	0.44638 (15)	0.0398 (3)
C9	0.93436 (16)	0.18710 (8)	0.47309 (16)	0.0435 (3)
H9	0.836671	0.186378	0.448048	0.052*
C10	0.99807 (17)	0.24766 (8)	0.53638 (17)	0.0456 (3)
H10	0.943157	0.287658	0.552522	0.055*
C11	1.14360 (16)	0.24932 (8)	0.57615 (15)	0.0410 (3)
C12	1.22777 (15)	0.18990 (8)	0.54966 (15)	0.0390 (3)
C13	1.16227 (15)	0.13017 (8)	0.48509 (15)	0.0397 (3)
H13	1.217489	0.090658	0.466589	0.048*
C14	1.38542 (17)	0.19118 (9)	0.59817 (18)	0.0473 (4)
H14A	1.401057	0.181264	0.698985	0.057*
H14B	1.431423	0.153440	0.549728	0.057*
C15	1.45567 (19)	0.27260 (10)	0.41787 (17)	0.0533 (4)
H15A	1.360309	0.272216	0.368303	0.064*
H15B	1.508851	0.233930	0.380183	0.064*
C16	1.5255 (2)	0.34382 (12)	0.3944 (2)	0.0645 (5)
H16A	1.529884	0.350654	0.293866	0.077*
H16B	1.468902	0.382512	0.427116	0.077*
C17	1.65806 (19)	0.33755 (12)	0.6150 (2)	0.0603 (5)
H17A	1.601485	0.375827	0.649325	0.072*
H17B	1.752902	0.340669	0.665265	0.072*
C18	1.59421 (16)	0.26603 (10)	0.64480 (18)	0.0507 (4)
H18A	1.652343	0.227514	0.613763	0.061*
H18B	1.591062	0.260745	0.745894	0.061*
N1	1.45003 (13)	0.26102 (7)	0.56999 (13)	0.0425 (3)
O1	1.03248 (13)	0.01683 (7)	0.32762 (15)	0.0605 (3)
O2	1.20139 (14)	0.30917 (7)	0.64087 (14)	0.0548 (3)
O3	1.66467 (14)	0.34704 (8)	0.46745 (15)	0.0686 (4)
S1	0.45988 (5)	0.02779 (3)	0.30547 (7)	0.0781 (2)
H1O	1.2875 (19)	0.3090 (18)	0.633 (3)	0.117*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0407 (9)	0.0815 (14)	0.0932 (15)	0.0020 (9)	0.0062 (9)	−0.0139 (12)
C2	0.0505 (10)	0.0600 (11)	0.0743 (13)	−0.0078 (8)	−0.0017 (9)	−0.0083 (9)
C3	0.0508 (9)	0.0475 (9)	0.0585 (10)	0.0007 (7)	0.0072 (7)	−0.0053 (7)
C4	0.0416 (8)	0.0406 (8)	0.0499 (8)	0.0049 (6)	0.0046 (6)	0.0006 (6)
C5	0.0417 (8)	0.0414 (7)	0.0515 (8)	0.0031 (6)	0.0073 (6)	0.0028 (6)
C6	0.0419 (8)	0.0443 (8)	0.0538 (9)	0.0012 (6)	0.0084 (7)	−0.0019 (7)
C7	0.0426 (8)	0.0413 (8)	0.0470 (8)	−0.0013 (6)	0.0094 (6)	0.0031 (6)
C8	0.0394 (7)	0.0408 (7)	0.0405 (7)	−0.0009 (6)	0.0098 (6)	0.0044 (6)
C9	0.0370 (7)	0.0476 (8)	0.0472 (8)	0.0017 (6)	0.0102 (6)	0.0029 (6)
C10	0.0451 (8)	0.0430 (8)	0.0505 (9)	0.0060 (6)	0.0132 (7)	−0.0018 (6)
C11	0.0468 (8)	0.0414 (7)	0.0359 (7)	−0.0002 (6)	0.0086 (6)	0.0015 (6)
C12	0.0388 (7)	0.0417 (7)	0.0367 (7)	0.0007 (6)	0.0052 (6)	0.0066 (6)
C13	0.0401 (7)	0.0372 (7)	0.0427 (7)	0.0034 (6)	0.0090 (6)	0.0049 (6)
C14	0.0427 (8)	0.0468 (8)	0.0509 (9)	0.0011 (6)	−0.0012 (6)	0.0040 (7)
C15	0.0532 (9)	0.0672 (11)	0.0389 (8)	−0.0119 (8)	0.0035 (7)	−0.0032 (7)
C16	0.0651 (11)	0.0769 (13)	0.0532 (10)	−0.0191 (10)	0.0138 (8)	0.0029 (9)
C17	0.0433 (9)	0.0802 (13)	0.0587 (10)	−0.0145 (8)	0.0114 (7)	−0.0211 (9)
C18	0.0379 (8)	0.0673 (11)	0.0461 (8)	0.0016 (7)	0.0016 (6)	−0.0121 (7)
N1	0.0376 (6)	0.0507 (7)	0.0388 (6)	−0.0043 (5)	0.0032 (5)	−0.0020 (5)
O1	0.0456 (6)	0.0539 (7)	0.0837 (9)	0.0002 (5)	0.0151 (6)	−0.0174 (6)
O2	0.0554 (7)	0.0482 (6)	0.0605 (7)	−0.0024 (5)	0.0059 (6)	−0.0127 (5)
O3	0.0540 (7)	0.0911 (10)	0.0646 (8)	−0.0251 (7)	0.0234 (6)	−0.0133 (7)
S1	0.0495 (3)	0.0889 (4)	0.0965 (4)	0.0074 (2)	0.0111 (3)	−0.0427 (3)

Geometric parameters (Å, º)

C1—C2	1.336 (3)	C11—C12	1.402 (2)
C1—S1	1.705 (2)	C12—C13	1.379 (2)
C1—H1	0.9300	C12—C14	1.513 (2)
C2—C3	1.406 (2)	C13—H13	0.9300
C2—H2	0.9300	C14—N1	1.472 (2)
C3—C4	1.368 (2)	C14—H14A	0.9700
C3—H3	0.9300	C14—H14B	0.9700
C4—C5	1.439 (2)	C15—N1	1.469 (2)
C4—S1	1.7197 (16)	C15—C16	1.507 (3)
C5—C6	1.325 (2)	C15—H15A	0.9700
C5—H5	0.9300	C15—H15B	0.9700
C6—C7	1.473 (2)	C16—O3	1.419 (2)
C6—H6	0.9300	C16—H16A	0.9700
C7—O1	1.2239 (19)	C16—H16B	0.9700
C7—C8	1.487 (2)	C17—O3	1.422 (2)
C8—C9	1.394 (2)	C17—C18	1.500 (3)
C8—C13	1.403 (2)	C17—H17A	0.9700
C9—C10	1.380 (2)	C17—H17B	0.9700
C9—H9	0.9300	C18—N1	1.4691 (19)
C10—C11	1.389 (2)	C18—H18A	0.9700
C10—H10	0.9300	C18—H18B	0.9700
C11—O2	1.3538 (19)	O2—H1O	0.830 (18)
C2—C1—S1	111.75 (15)	C8—C13—H13	118.9
C2—C1—H1	124.1	N1—C14—C12	112.14 (12)
S1—C1—H1	124.1	N1—C14—H14A	109.2
C1—C2—C3	113.02 (18)	C12—C14—H14A	109.2
C1—C2—H2	123.5	N1—C14—H14B	109.2
C3—C2—H2	123.5	C12—C14—H14B	109.2
C4—C3—C2	113.24 (16)	H14A—C14—H14B	107.9
C4—C3—H3	123.4	N1—C15—C16	109.98 (14)
C2—C3—H3	123.4	N1—C15—H15A	109.7
C3—C4—C5	126.63 (15)	C16—C15—H15A	109.7
C3—C4—S1	109.79 (12)	N1—C15—H15B	109.7
C5—C4—S1	123.58 (12)	C16—C15—H15B	109.7
C6—C5—C4	127.99 (15)	H15A—C15—H15B	108.2
C6—C5—H5	116.0	O3—C16—C15	111.42 (17)
C4—C5—H5	116.0	O3—C16—H16A	109.3
C5—C6—C7	120.90 (15)	C15—C16—H16A	109.3
C5—C6—H6	119.6	O3—C16—H16B	109.3
C7—C6—H6	119.6	C15—C16—H16B	109.3
O1—C7—C6	120.42 (14)	H16A—C16—H16B	108.0
O1—C7—C8	119.90 (14)	O3—C17—C18	111.22 (14)
C6—C7—C8	119.67 (13)	O3—C17—H17A	109.4
C9—C8—C13	118.09 (14)	C18—C17—H17A	109.4
C9—C8—C7	123.12 (14)	O3—C17—H17B	109.4
C13—C8—C7	118.69 (13)	C18—C17—H17B	109.4
C10—C9—C8	120.57 (14)	H17A—C17—H17B	108.0
C10—C9—H9	119.7	N1—C18—C17	109.80 (15)
C8—C9—H9	119.7	N1—C18—H18A	109.7
C9—C10—C11	120.48 (14)	C17—C18—H18A	109.7
C9—C10—H10	119.8	N1—C18—H18B	109.7
C11—C10—H10	119.8	C17—C18—H18B	109.7
O2—C11—C10	118.59 (14)	H18A—C18—H18B	108.2
O2—C11—C12	121.18 (14)	C18—N1—C15	109.09 (13)
C10—C11—C12	120.23 (14)	C18—N1—C14	110.61 (13)
C13—C12—C11	118.39 (13)	C15—N1—C14	111.86 (13)
C13—C12—C14	121.74 (13)	C11—O2—H1O	108 (2)
C11—C12—C14	119.80 (13)	C16—O3—C17	109.29 (13)
C12—C13—C8	122.22 (13)	C1—S1—C4	92.20 (9)
C12—C13—H13	118.9
S1—C1—C2—C3	0.3 (3)	C10—C11—C12—C14	−177.78 (14)
C1—C2—C3—C4	0.4 (3)	C11—C12—C13—C8	−0.4 (2)
C2—C3—C4—C5	178.40 (16)	C14—C12—C13—C8	176.60 (13)
C2—C3—C4—S1	−0.9 (2)	C9—C8—C13—C12	0.9 (2)
C3—C4—C5—C6	179.33 (18)	C7—C8—C13—C12	177.50 (13)
S1—C4—C5—C6	−1.5 (3)	C13—C12—C14—N1	140.07 (14)
C4—C5—C6—C7	179.26 (15)	C11—C12—C14—N1	−42.94 (19)
C5—C6—C7—O1	−13.9 (3)	N1—C15—C16—O3	58.3 (2)
C5—C6—C7—C8	165.08 (15)	O3—C17—C18—N1	−59.52 (19)
O1—C7—C8—C9	166.04 (15)	C17—C18—N1—C15	56.66 (17)
C6—C7—C8—C9	−12.9 (2)	C17—C18—N1—C14	−179.90 (13)
O1—C7—C8—C13	−10.4 (2)	C16—C15—N1—C18	−55.98 (19)
C6—C7—C8—C13	170.68 (14)	C16—C15—N1—C14	−178.68 (15)
C13—C8—C9—C10	−0.3 (2)	C12—C14—N1—C18	167.76 (13)
C7—C8—C9—C10	−176.70 (14)	C12—C14—N1—C15	−70.41 (17)
C8—C9—C10—C11	−0.8 (2)	C15—C16—O3—C17	−59.5 (2)
C9—C10—C11—O2	−178.50 (14)	C18—C17—O3—C16	60.1 (2)
C9—C10—C11—C12	1.3 (2)	C2—C1—S1—C4	−0.7 (2)
O2—C11—C12—C13	179.13 (13)	C3—C4—S1—C1	0.90 (15)
C10—C11—C12—C13	−0.7 (2)	C5—C4—S1—C1	−178.40 (16)
O2—C11—C12—C14	2.0 (2)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O···N1	0.83 (2)	1.94 (2)	2.6834 (18)	149 (3)
C1—H1···O1^i	0.93	2.38	3.249 (2)	156
C2—H2···O2^ii	0.93	2.57	3.417 (2)	152
C5—H5···O1	0.93	2.45	2.786 (2)	101
C16—H16A···Cg1^iii	0.97	2.88	3.789 (2)	157
C18—H18B···Cg1^iv	0.97	2.70	3.6010 (18)	154

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