Crystal structure and Hirshfeld surface analysis of (Z)-2-amino-4-(2,6-di­chloro­phen­yl)-5-(1-hy­droxy­ethyl­idene)-6-oxo-1-phenyl-1,4,5,6-tetra­hydro­pyridine-3-carbo­nitrile

The mol­ecular conformation of the title compound is stabilized by an intra­molecular O—H...O hydrogen bond, forming an S(6) ring motif. Inter­molecular N—H...N and C—H...N hydrogen bonds, as well as N—H...π and C—H...π inter­actions create a three-dimensional network in the crystal.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.053
• wR factor = 0.126
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00435 Ang.
PLAT420_ALERT_2_C D-H Bond Without Acceptor  N3       --H3B      .     Please Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.397 Check

Alert level G
PLAT230_ALERT_2_G Hirshfeld Test Diff for    N2       --C20      .        6.0 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C5       --C20      .        6.5 s.u.
PLAT793_ALERT_4_G Model has Chirality at C4          (Centro SPGR)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          6 Note
PLAT954_ALERT_1_G Reported (CIF) and Actual (FCF) Kmax Differ by .          1 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 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
   7 ALERT level G = General information/check it is not something unexpected

   1 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
   3 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
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

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

---

Computing details

Data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

(Z)-2-Amino-4-(2,6-dichlorophenyl)-5-(1-hydroxyethylidene)-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile

Crystal data

C20H15Cl2N3O2	F(000) = 824
Mr = 400.25	Dx = 1.465 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.662 (1) Å	Cell parameters from 2887 reflections
b = 27.010 (3) Å	θ = 2.3–25.6°
c = 7.4782 (8) Å	µ = 0.38 mm^−1
β = 111.571 (2)°	T = 100 K
V = 1814.9 (3) Å^3	Plate, colourless
Z = 4	0.24 × 0.21 × 0.02 mm

Data collection

Bruker D8 QUEST PHOTON-III CCD diffractometer	2631 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.099
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 27.5°, θmin = 2.3°
Tmin = 0.864, Tmax = 0.986	h = −12→12
27440 measured reflections	k = −35→35
4180 independent reflections	l = −9→9

Refinement

Refinement on F^2	Secondary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.126	w = 1/[σ^2(Fo^2) + (0.0387P)^2 + 2.0157P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
4180 reflections	Δρmax = 0.50 e Å^−3
255 parameters	Δρmin = −0.37 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: dual	Extinction coefficient: 0.0024 (2)

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
Cl1	0.86090 (9)	0.51416 (3)	0.60657 (12)	0.0256 (2)
Cl2	0.73128 (9)	0.32459 (3)	0.75788 (12)	0.0262 (2)
O1	0.3936 (2)	0.32320 (9)	0.2910 (3)	0.0280 (5)
O2	0.5668 (3)	0.34472 (9)	0.1210 (3)	0.0286 (6)
H2	0.502 (4)	0.3295 (15)	0.155 (6)	0.043*
N1	0.3832 (3)	0.36887 (10)	0.5389 (4)	0.0190 (6)
N2	0.6028 (3)	0.51570 (10)	0.8819 (4)	0.0213 (6)
N3	0.3468 (3)	0.41829 (11)	0.7719 (4)	0.0216 (6)
H3A	0.376 (4)	0.4411 (13)	0.857 (5)	0.026*
H3B	0.275 (4)	0.3976 (13)	0.763 (5)	0.026*
C1	0.6193 (3)	0.38087 (12)	0.2516 (4)	0.0222 (7)
C2	0.4484 (3)	0.35814 (12)	0.4048 (4)	0.0215 (7)
C3	0.5700 (3)	0.38792 (12)	0.3994 (4)	0.0190 (7)
C4	0.6393 (3)	0.42841 (12)	0.5454 (4)	0.0185 (7)
H4	0.6402	0.4592	0.4717	0.022*
C5	0.5438 (3)	0.43903 (11)	0.6633 (4)	0.0178 (6)
C6	0.4288 (3)	0.40975 (12)	0.6622 (4)	0.0190 (6)
C7	0.2636 (3)	0.33754 (11)	0.5457 (4)	0.0182 (6)
C8	0.2954 (3)	0.29874 (12)	0.6757 (4)	0.0225 (7)
H8	0.3954	0.2923	0.7572	0.027*
C9	0.1808 (4)	0.26931 (12)	0.6866 (5)	0.0247 (7)
H9	0.2018	0.2428	0.7762	0.030*
C10	0.0355 (4)	0.27893 (12)	0.5655 (5)	0.0254 (7)
H10	−0.0431	0.2588	0.5722	0.030*
C11	0.0039 (3)	0.31762 (12)	0.4351 (5)	0.0233 (7)
H11	−0.0959	0.3239	0.3526	0.028*
C12	0.1182 (3)	0.34720 (12)	0.4251 (4)	0.0219 (7)
H12	0.0970	0.3739	0.3362	0.026*
C13	0.7339 (4)	0.41270 (13)	0.2175 (5)	0.0262 (7)
H13A	0.7588	0.3988	0.1121	0.039*
H13B	0.8235	0.4139	0.3346	0.039*
H13C	0.6943	0.4462	0.1834	0.039*
C14	0.8003 (3)	0.41904 (12)	0.6829 (4)	0.0168 (6)
C15	0.9070 (3)	0.45717 (12)	0.7254 (4)	0.0206 (7)
C16	1.0502 (3)	0.45270 (13)	0.8591 (5)	0.0237 (7)
H16	1.1177	0.4797	0.8851	0.028*
C17	1.0934 (3)	0.40785 (13)	0.9546 (4)	0.0252 (7)
H17	1.1915	0.4041	1.0469	0.030*
C18	0.9949 (3)	0.36865 (13)	0.9164 (5)	0.0238 (7)
H18	1.0255	0.3378	0.9793	0.029*
C19	0.8510 (3)	0.37491 (12)	0.7852 (4)	0.0194 (7)
C20	0.5773 (3)	0.48144 (12)	0.7841 (4)	0.0190 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0223 (4)	0.0243 (4)	0.0291 (4)	−0.0013 (3)	0.0083 (3)	0.0025 (4)
Cl2	0.0236 (4)	0.0258 (4)	0.0260 (4)	−0.0006 (3)	0.0056 (3)	0.0049 (4)
O1	0.0271 (12)	0.0342 (14)	0.0240 (12)	−0.0085 (11)	0.0108 (10)	−0.0124 (11)
O2	0.0296 (13)	0.0394 (15)	0.0171 (12)	−0.0043 (11)	0.0091 (10)	−0.0072 (11)
N1	0.0169 (13)	0.0243 (15)	0.0161 (13)	−0.0028 (11)	0.0063 (10)	−0.0035 (11)
N2	0.0213 (14)	0.0210 (14)	0.0200 (14)	−0.0026 (11)	0.0058 (11)	−0.0030 (12)
N3	0.0199 (14)	0.0270 (15)	0.0196 (14)	−0.0071 (12)	0.0095 (11)	−0.0081 (12)
C1	0.0210 (16)	0.0286 (18)	0.0135 (15)	0.0038 (13)	0.0022 (12)	−0.0012 (14)
C2	0.0200 (15)	0.0275 (18)	0.0160 (15)	0.0009 (13)	0.0053 (12)	−0.0023 (14)
C3	0.0174 (15)	0.0225 (17)	0.0152 (15)	−0.0002 (12)	0.0038 (12)	−0.0001 (13)
C4	0.0157 (15)	0.0228 (17)	0.0166 (15)	0.0014 (12)	0.0055 (12)	−0.0020 (13)
C5	0.0172 (15)	0.0207 (16)	0.0139 (15)	0.0005 (12)	0.0037 (12)	−0.0014 (13)
C6	0.0162 (14)	0.0237 (17)	0.0135 (15)	0.0036 (12)	0.0012 (12)	−0.0002 (13)
C7	0.0175 (15)	0.0185 (16)	0.0184 (15)	−0.0037 (12)	0.0062 (12)	−0.0048 (13)
C8	0.0201 (16)	0.0264 (18)	0.0174 (16)	0.0015 (13)	0.0026 (13)	−0.0003 (14)
C9	0.0275 (17)	0.0219 (17)	0.0254 (18)	0.0030 (14)	0.0106 (14)	0.0049 (14)
C10	0.0228 (16)	0.0245 (18)	0.0310 (19)	−0.0028 (14)	0.0124 (14)	−0.0042 (15)
C11	0.0177 (15)	0.0259 (18)	0.0223 (17)	0.0019 (13)	0.0024 (13)	0.0013 (14)
C12	0.0230 (16)	0.0224 (17)	0.0177 (16)	0.0031 (13)	0.0044 (13)	0.0001 (13)
C13	0.0264 (17)	0.033 (2)	0.0206 (17)	0.0037 (15)	0.0107 (14)	0.0041 (15)
C14	0.0152 (14)	0.0241 (16)	0.0126 (14)	0.0025 (12)	0.0070 (11)	−0.0011 (12)
C15	0.0200 (15)	0.0254 (17)	0.0179 (16)	0.0040 (13)	0.0088 (13)	0.0024 (14)
C16	0.0185 (15)	0.0315 (19)	0.0222 (17)	−0.0020 (13)	0.0089 (13)	−0.0035 (14)
C17	0.0162 (15)	0.042 (2)	0.0173 (16)	0.0027 (14)	0.0063 (13)	−0.0010 (15)
C18	0.0219 (16)	0.0307 (19)	0.0196 (16)	0.0047 (14)	0.0087 (13)	0.0047 (14)
C19	0.0174 (15)	0.0266 (17)	0.0150 (15)	−0.0009 (13)	0.0066 (12)	−0.0022 (13)
C20	0.0110 (14)	0.0270 (18)	0.0193 (16)	0.0044 (12)	0.0058 (12)	0.0062 (14)

Geometric parameters (Å, º)

Cl1—C15	1.751 (3)	C7—C12	1.387 (4)
Cl2—C19	1.747 (3)	C8—C9	1.390 (4)
O1—C2	1.250 (4)	C8—H8	0.9500
O2—C1	1.342 (4)	C9—C10	1.387 (4)
O2—H2	0.86 (4)	C9—H9	0.9500
N1—C2	1.397 (4)	C10—C11	1.385 (5)
N1—C6	1.401 (4)	C10—H10	0.9500
N1—C7	1.448 (4)	C11—C12	1.387 (4)
N2—C20	1.149 (4)	C11—H11	0.9500
N3—C6	1.354 (4)	C12—H12	0.9500
N3—H3A	0.86 (4)	C13—H13A	0.9800
N3—H3B	0.88 (4)	C13—H13B	0.9800
C1—C3	1.368 (4)	C13—H13C	0.9800
C1—C13	1.496 (4)	C14—C19	1.404 (4)
C2—C3	1.437 (4)	C14—C15	1.408 (4)
C3—C4	1.516 (4)	C15—C16	1.382 (4)
C4—C5	1.519 (4)	C16—C17	1.390 (5)
C4—C14	1.538 (4)	C16—H16	0.9500
C4—H4	1.0000	C17—C18	1.382 (5)
C5—C6	1.361 (4)	C17—H17	0.9500
C5—C20	1.421 (4)	C18—C19	1.386 (4)
C7—C8	1.385 (4)	C18—H18	0.9500
C1—O2—H2	105 (3)	C8—C9—H9	120.3
C2—N1—C6	121.3 (3)	C11—C10—C9	120.6 (3)
C2—N1—C7	118.7 (2)	C11—C10—H10	119.7
C6—N1—C7	120.0 (2)	C9—C10—H10	119.7
C6—N3—H3A	118 (2)	C10—C11—C12	120.0 (3)
C6—N3—H3B	118 (2)	C10—C11—H11	120.0
H3A—N3—H3B	123 (3)	C12—C11—H11	120.0
O2—C1—C3	122.6 (3)	C11—C12—C7	119.5 (3)
O2—C1—C13	113.5 (3)	C11—C12—H12	120.2
C3—C1—C13	123.8 (3)	C7—C12—H12	120.2
O1—C2—N1	117.1 (3)	C1—C13—H13A	109.5
O1—C2—C3	123.3 (3)	C1—C13—H13B	109.5
N1—C2—C3	119.6 (3)	H13A—C13—H13B	109.5
C1—C3—C2	118.4 (3)	C1—C13—H13C	109.5
C1—C3—C4	119.4 (3)	H13A—C13—H13C	109.5
C2—C3—C4	122.1 (3)	H13B—C13—H13C	109.5
C3—C4—C5	110.7 (2)	C19—C14—C15	114.7 (3)
C3—C4—C14	115.6 (2)	C19—C14—C4	124.6 (3)
C5—C4—C14	108.9 (2)	C15—C14—C4	120.5 (3)
C3—C4—H4	107.1	C16—C15—C14	123.7 (3)
C5—C4—H4	107.1	C16—C15—Cl1	116.4 (3)
C14—C4—H4	107.1	C14—C15—Cl1	120.0 (2)
C6—C5—C20	117.8 (3)	C15—C16—C17	118.7 (3)
C6—C5—C4	123.7 (3)	C15—C16—H16	120.7
C20—C5—C4	118.4 (3)	C17—C16—H16	120.7
N3—C6—C5	123.7 (3)	C18—C17—C16	120.5 (3)
N3—C6—N1	114.8 (3)	C18—C17—H17	119.8
C5—C6—N1	121.4 (3)	C16—C17—H17	119.8
C8—C7—C12	120.6 (3)	C17—C18—C19	119.2 (3)
C8—C7—N1	119.5 (3)	C17—C18—H18	120.4
C12—C7—N1	119.9 (3)	C19—C18—H18	120.4
C7—C8—C9	119.9 (3)	C18—C19—C14	123.2 (3)
C7—C8—H8	120.1	C18—C19—Cl2	115.9 (3)
C9—C8—H8	120.1	C14—C19—Cl2	120.9 (2)
C10—C9—C8	119.5 (3)	N2—C20—C5	179.2 (3)
C10—C9—H9	120.3
C6—N1—C2—O1	−174.8 (3)	C6—N1—C7—C8	−86.5 (4)
C7—N1—C2—O1	3.5 (4)	C2—N1—C7—C12	−86.2 (4)
C6—N1—C2—C3	3.4 (4)	C6—N1—C7—C12	92.2 (3)
C7—N1—C2—C3	−178.2 (3)	C12—C7—C8—C9	−0.4 (5)
O2—C1—C3—C2	−5.5 (5)	N1—C7—C8—C9	178.3 (3)
C13—C1—C3—C2	173.5 (3)	C7—C8—C9—C10	0.5 (5)
O2—C1—C3—C4	177.7 (3)	C8—C9—C10—C11	−0.3 (5)
C13—C1—C3—C4	−3.3 (5)	C9—C10—C11—C12	−0.1 (5)
O1—C2—C3—C1	6.4 (5)	C10—C11—C12—C7	0.3 (5)
N1—C2—C3—C1	−171.7 (3)	C8—C7—C12—C11	0.0 (5)
O1—C2—C3—C4	−176.9 (3)	N1—C7—C12—C11	−178.7 (3)
N1—C2—C3—C4	5.0 (4)	C3—C4—C14—C19	−48.4 (4)
C1—C3—C4—C5	165.1 (3)	C5—C4—C14—C19	76.9 (4)
C2—C3—C4—C5	−11.6 (4)	C3—C4—C14—C15	136.5 (3)
C1—C3—C4—C14	−70.5 (4)	C5—C4—C14—C15	−98.2 (3)
C2—C3—C4—C14	112.8 (3)	C19—C14—C15—C16	−1.0 (4)
C3—C4—C5—C6	11.6 (4)	C4—C14—C15—C16	174.6 (3)
C14—C4—C5—C6	−116.5 (3)	C19—C14—C15—Cl1	179.1 (2)
C3—C4—C5—C20	−169.4 (3)	C4—C14—C15—Cl1	−5.3 (4)
C14—C4—C5—C20	62.5 (4)	C14—C15—C16—C17	1.4 (5)
C20—C5—C6—N3	−1.3 (5)	Cl1—C15—C16—C17	−178.7 (2)
C4—C5—C6—N3	177.7 (3)	C15—C16—C17—C18	0.0 (5)
C20—C5—C6—N1	176.3 (3)	C16—C17—C18—C19	−1.7 (5)
C4—C5—C6—N1	−4.7 (5)	C17—C18—C19—C14	2.2 (5)
C2—N1—C6—N3	174.1 (3)	C17—C18—C19—Cl2	−176.1 (2)
C7—N1—C6—N3	−4.2 (4)	C15—C14—C19—C18	−0.8 (4)
C2—N1—C6—C5	−3.6 (4)	C4—C14—C19—C18	−176.2 (3)
C7—N1—C6—C5	178.0 (3)	C15—C14—C19—Cl2	177.3 (2)
C2—N1—C7—C8	95.1 (3)	C4—C14—C19—Cl2	1.9 (4)

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the C7–C12 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.86 (4)	1.72 (4)	2.514 (3)	153 (4)
N3—H3A···N2^i	0.86 (4)	2.22 (4)	3.032 (4)	159 (3)
C16—H16···N2^ii	0.95	2.62	3.308 (4)	129
N3—H3B···Cg2	0.88 (4)	2.88 (4)	3.581 (3)	138 (3)
C9—H9···Cg2^iii	0.95	2.70	3.564 (4)	151

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