(4Z)-4-[1-(2-Amino­anilino)ethyl­idene]-3-methyl-1-phenyl-4,5-di­hydro-1H-pyrazol-5-one

The conformation of the title compound, C₁₈H₁₈N₄O, is partly determined by an intra­molecular N—H...O hydrogen bond that imposes planarity on the central amino­ethyl­idene-3-methyl­pyrazol-5-one segment of the mol­ecule. In the crystal, N—H...O hydrogen and N—H...N hydrogen bonds both form centrosymmetric dimers that enclose R₂²(18) rings. These, together with C—H...N and π–π stacking inter­actions between centrosymmetrically related pyraza­lone rings, stack the mol­ecules along the b-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.038
• wR factor = 0.096
• Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11C   ..  N1      ..       2.68 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         23 Report

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
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         41 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 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
   4 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(4Z)-4-[1-(2-Aminoanilino)ethylidene]-3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one

Crystal data

C18H18N4O	F(000) = 648
Mr = 306.36	Dx = 1.297 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 8.6575 (2) Å	Cell parameters from 8108 reflections
b = 7.1749 (1) Å	θ = 5.1–72.4°
c = 25.3062 (5) Å	µ = 0.67 mm^−1
β = 93.782 (1)°	T = 150 K
V = 1568.51 (5) Å^3	Column, colourless
Z = 4	0.19 × 0.05 × 0.05 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3032 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2596 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.035
Detector resolution: 10.4167 pixels mm^-1	θmax = 72.4°, θmin = 5.1°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −8→8
Tmin = 0.87, Tmax = 0.97	l = −31→30
11756 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.038	w = 1/[σ^2(Fo^2) + (0.0455P)^2 + 0.4468P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.096	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.29 e Å^−3
3032 reflections	Δρmin = −0.18 e Å^−3
281 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0050 (4)

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 > 2sigma(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
O1	0.23306 (10)	0.69400 (14)	0.45467 (4)	0.0305 (2)
N1	0.48083 (12)	0.71074 (15)	0.42251 (4)	0.0248 (2)
N2	0.63327 (12)	0.73552 (16)	0.44323 (4)	0.0270 (3)
N3	0.25320 (13)	0.75094 (16)	0.56022 (4)	0.0276 (3)
C1	0.62652 (14)	0.75905 (17)	0.49448 (5)	0.0248 (3)
C2	0.47020 (14)	0.74833 (17)	0.50980 (5)	0.0234 (3)
C3	0.37694 (14)	0.71531 (17)	0.46141 (5)	0.0241 (3)
H3	0.203 (2)	0.721 (2)	0.5265 (7)	0.044 (5)*
C4	0.45262 (15)	0.68737 (17)	0.36708 (5)	0.0258 (3)
H4A	0.132 (2)	0.447 (3)	0.5721 (8)	0.051 (5)*
H4B	−0.032 (2)	0.404 (3)	0.5913 (8)	0.057 (6)*
N4	0.05992 (15)	0.47138 (18)	0.59596 (6)	0.0405 (3)
C5	0.30760 (17)	0.7256 (2)	0.34286 (5)	0.0316 (3)
H5	0.221 (2)	0.771 (2)	0.3632 (7)	0.040 (4)*
C6	0.28126 (19)	0.6947 (2)	0.28880 (6)	0.0406 (4)
H6	0.179 (2)	0.722 (3)	0.2718 (7)	0.047 (5)*
C7	0.3984 (2)	0.6291 (3)	0.25907 (6)	0.0451 (4)
H7	0.379 (2)	0.604 (3)	0.2209 (8)	0.057 (5)*
C8	0.5442 (2)	0.5994 (2)	0.28307 (6)	0.0417 (4)
H8	0.631 (2)	0.552 (3)	0.2629 (7)	0.052 (5)*
C9	0.57317 (17)	0.6281 (2)	0.33724 (6)	0.0332 (3)
H9	0.680 (2)	0.607 (2)	0.3542 (6)	0.037 (4)*
C10	0.77427 (16)	0.7937 (2)	0.52661 (6)	0.0338 (3)
H10A	0.769 (2)	0.910 (3)	0.5479 (7)	0.045 (5)*
H10B	0.795 (2)	0.693 (3)	0.5525 (8)	0.054 (5)*
H10C	0.862 (2)	0.799 (3)	0.5015 (8)	0.049 (5)*
C11	0.50207 (16)	0.8055 (2)	0.60909 (5)	0.0294 (3)
H11A	0.450 (2)	0.766 (3)	0.6404 (8)	0.056 (5)*
H11B	0.601 (2)	0.738 (3)	0.6094 (8)	0.054 (5)*
H11C	0.527 (2)	0.938 (3)	0.6128 (8)	0.063 (6)*
C12	0.40601 (15)	0.76834 (17)	0.55887 (5)	0.0242 (3)
C13	0.16041 (15)	0.78645 (19)	0.60397 (5)	0.0266 (3)
C14	0.05963 (14)	0.64562 (19)	0.61874 (5)	0.0284 (3)
C15	−0.04064 (16)	0.6879 (2)	0.65830 (6)	0.0341 (3)
H15	−0.113 (2)	0.588 (3)	0.6692 (7)	0.045 (5)*
C16	−0.04014 (16)	0.8615 (2)	0.68174 (6)	0.0366 (3)
H16	−0.112 (2)	0.889 (3)	0.7101 (7)	0.046 (5)*
C17	0.06066 (17)	0.9995 (2)	0.66678 (6)	0.0367 (3)
H17	0.062 (2)	1.130 (3)	0.6819 (7)	0.050 (5)*
C18	0.15980 (16)	0.9615 (2)	0.62736 (5)	0.0325 (3)
H18	0.2297 (18)	1.060 (2)	0.6150 (6)	0.037 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0219 (4)	0.0418 (6)	0.0276 (5)	−0.0053 (4)	0.0004 (3)	−0.0017 (4)
N1	0.0222 (5)	0.0283 (6)	0.0236 (5)	−0.0018 (4)	0.0002 (4)	0.0002 (4)
N2	0.0223 (5)	0.0285 (6)	0.0301 (6)	−0.0015 (4)	0.0006 (4)	0.0002 (5)
N3	0.0266 (6)	0.0329 (6)	0.0232 (5)	−0.0051 (5)	0.0022 (4)	−0.0021 (5)
C1	0.0243 (6)	0.0210 (6)	0.0289 (6)	−0.0004 (5)	−0.0003 (5)	0.0008 (5)
C2	0.0244 (6)	0.0215 (6)	0.0243 (6)	−0.0010 (5)	−0.0002 (5)	0.0003 (5)
C3	0.0244 (6)	0.0226 (6)	0.0253 (6)	−0.0015 (5)	0.0016 (5)	0.0010 (5)
C4	0.0325 (7)	0.0213 (6)	0.0235 (6)	−0.0048 (5)	0.0025 (5)	0.0009 (5)
N4	0.0266 (6)	0.0327 (7)	0.0626 (9)	−0.0049 (5)	0.0061 (6)	−0.0072 (6)
C5	0.0326 (7)	0.0354 (8)	0.0267 (6)	−0.0071 (6)	0.0006 (5)	0.0046 (6)
C6	0.0432 (8)	0.0506 (9)	0.0274 (7)	−0.0149 (7)	−0.0036 (6)	0.0073 (7)
C7	0.0627 (10)	0.0494 (10)	0.0233 (7)	−0.0182 (8)	0.0034 (7)	0.0001 (7)
C8	0.0562 (10)	0.0385 (9)	0.0321 (7)	−0.0047 (7)	0.0146 (7)	−0.0037 (7)
C9	0.0386 (8)	0.0292 (7)	0.0323 (7)	0.0000 (6)	0.0067 (6)	−0.0004 (6)
C10	0.0249 (7)	0.0394 (8)	0.0363 (7)	−0.0009 (6)	−0.0041 (6)	−0.0039 (7)
C11	0.0323 (7)	0.0300 (7)	0.0254 (6)	−0.0018 (6)	−0.0021 (5)	−0.0013 (6)
C12	0.0275 (6)	0.0193 (6)	0.0257 (6)	−0.0019 (5)	0.0010 (5)	0.0017 (5)
C13	0.0243 (6)	0.0328 (7)	0.0229 (6)	−0.0019 (5)	0.0014 (5)	0.0021 (5)
C14	0.0218 (6)	0.0303 (7)	0.0324 (7)	−0.0008 (5)	−0.0032 (5)	0.0045 (6)
C15	0.0246 (6)	0.0406 (8)	0.0375 (7)	−0.0016 (6)	0.0038 (5)	0.0093 (6)
C16	0.0305 (7)	0.0493 (9)	0.0309 (7)	0.0033 (6)	0.0075 (6)	0.0031 (7)
C17	0.0374 (8)	0.0386 (8)	0.0345 (7)	0.0002 (6)	0.0060 (6)	−0.0040 (7)
C18	0.0337 (7)	0.0328 (7)	0.0316 (7)	−0.0057 (6)	0.0061 (6)	−0.0009 (6)

Geometric parameters (Å, º)

O1—C3	1.2554 (15)	C7—H7	0.985 (19)
N1—C3	1.3769 (16)	C8—C9	1.392 (2)
N1—N2	1.3990 (15)	C8—H8	0.999 (19)
N1—C4	1.4178 (16)	C9—H9	1.008 (17)
N2—C1	1.3132 (17)	C10—H10A	0.99 (2)
N3—C12	1.3316 (17)	C10—H10B	0.98 (2)
N3—C13	1.4330 (16)	C10—H10C	1.021 (19)
N3—H3	0.955 (18)	C11—C12	1.4962 (18)
C1—C2	1.4342 (17)	C11—H11A	0.98 (2)
C1—C10	1.4906 (18)	C11—H11B	0.99 (2)
C2—C12	1.4007 (17)	C11—H11C	0.98 (2)
C2—C3	1.4413 (17)	C13—C18	1.388 (2)
C4—C5	1.3878 (19)	C13—C14	1.4017 (18)
C4—C9	1.3945 (19)	C14—C15	1.4007 (19)
N4—C14	1.3768 (19)	C15—C16	1.380 (2)
N4—H4A	0.92 (2)	C15—H15	1.000 (18)
N4—H4B	0.93 (2)	C16—C17	1.389 (2)
C5—C6	1.390 (2)	C16—H16	1.002 (18)
C5—H5	0.991 (17)	C17—C18	1.385 (2)
C6—C7	1.385 (2)	C17—H17	1.01 (2)
C6—H6	0.976 (19)	C18—H18	0.997 (17)
C7—C8	1.380 (2)
C3—N1—N2	111.94 (10)	C8—C9—H9	119.9 (9)
C3—N1—C4	129.21 (11)	C4—C9—H9	121.1 (9)
N2—N1—C4	118.84 (10)	C1—C10—H10A	111.7 (10)
C1—N2—N1	106.51 (10)	C1—C10—H10B	110.7 (12)
C12—N3—C13	127.72 (11)	H10A—C10—H10B	105.5 (15)
C12—N3—H3	112.9 (11)	C1—C10—H10C	108.2 (11)
C13—N3—H3	119.2 (11)	H10A—C10—H10C	111.5 (14)
N2—C1—C2	111.37 (11)	H10B—C10—H10C	109.2 (15)
N2—C1—C10	117.88 (12)	C12—C11—H11A	112.0 (12)
C2—C1—C10	130.74 (12)	C12—C11—H11B	110.7 (11)
C12—C2—C1	132.12 (12)	H11A—C11—H11B	107.4 (16)
C12—C2—C3	122.50 (11)	C12—C11—H11C	111.3 (12)
C1—C2—C3	105.35 (11)	H11A—C11—H11C	108.4 (16)
O1—C3—N1	126.09 (11)	H11B—C11—H11C	106.8 (16)
O1—C3—C2	129.10 (11)	N3—C12—C2	117.79 (11)
N1—C3—C2	104.81 (10)	N3—C12—C11	119.49 (11)
C5—C4—C9	120.57 (13)	C2—C12—C11	122.72 (12)
C5—C4—N1	120.36 (12)	C18—C13—C14	121.23 (12)
C9—C4—N1	119.06 (12)	C18—C13—N3	120.55 (12)
C14—N4—H4A	118.0 (13)	C14—C13—N3	117.93 (12)
C14—N4—H4B	120.0 (12)	N4—C14—C15	120.93 (13)
H4A—N4—H4B	115.7 (17)	N4—C14—C13	121.64 (13)
C4—C5—C6	119.22 (14)	C15—C14—C13	117.42 (13)
C4—C5—H5	121.8 (10)	C16—C15—C14	121.21 (13)
C6—C5—H5	118.9 (10)	C16—C15—H15	120.8 (10)
C7—C6—C5	120.70 (15)	C14—C15—H15	118.0 (10)
C7—C6—H6	120.2 (11)	C15—C16—C17	120.71 (13)
C5—C6—H6	119.1 (11)	C15—C16—H16	120.0 (11)
C8—C7—C6	119.64 (14)	C17—C16—H16	119.3 (11)
C8—C7—H7	119.9 (11)	C18—C17—C16	119.10 (14)
C6—C7—H7	120.5 (11)	C18—C17—H17	117.6 (10)
C7—C8—C9	120.70 (14)	C16—C17—H17	123.2 (10)
C7—C8—H8	121.8 (11)	C17—C18—C13	120.32 (13)
C9—C8—H8	117.5 (11)	C17—C18—H18	120.3 (9)
C8—C9—C4	119.05 (14)	C13—C18—H18	119.4 (9)
C3—N1—N2—C1	−1.13 (14)	C6—C7—C8—C9	2.4 (3)
C4—N1—N2—C1	178.18 (11)	C7—C8—C9—C4	0.1 (2)
N1—N2—C1—C2	0.78 (14)	C5—C4—C9—C8	−3.0 (2)
N1—N2—C1—C10	−178.48 (12)	N1—C4—C9—C8	177.95 (13)
N2—C1—C2—C12	−178.39 (13)	C13—N3—C12—C2	−172.18 (12)
C10—C1—C2—C12	0.7 (2)	C13—N3—C12—C11	8.6 (2)
N2—C1—C2—C3	−0.19 (14)	C1—C2—C12—N3	179.71 (13)
C10—C1—C2—C3	178.94 (14)	C3—C2—C12—N3	1.77 (18)
N2—N1—C3—O1	−178.75 (12)	C1—C2—C12—C11	−1.1 (2)
C4—N1—C3—O1	2.0 (2)	C3—C2—C12—C11	−179.04 (12)
N2—N1—C3—C2	0.99 (14)	C12—N3—C13—C18	58.78 (19)
C4—N1—C3—C2	−178.23 (12)	C12—N3—C13—C14	−127.44 (14)
C12—C2—C3—O1	−2.3 (2)	C18—C13—C14—N4	−179.68 (13)
C1—C2—C3—O1	179.25 (13)	N3—C13—C14—N4	6.59 (19)
C12—C2—C3—N1	177.93 (11)	C18—C13—C14—C15	−0.54 (19)
C1—C2—C3—N1	−0.48 (13)	N3—C13—C14—C15	−174.28 (12)
C3—N1—C4—C5	21.3 (2)	N4—C14—C15—C16	179.20 (13)
N2—N1—C4—C5	−157.89 (12)	C13—C14—C15—C16	0.1 (2)
C3—N1—C4—C9	−159.63 (13)	C14—C15—C16—C17	−0.2 (2)
N2—N1—C4—C9	21.19 (17)	C15—C16—C17—C18	0.8 (2)
C9—C4—C5—C6	3.4 (2)	C16—C17—C18—C13	−1.3 (2)
N1—C4—C5—C6	−177.52 (13)	C14—C13—C18—C17	1.2 (2)
C4—C5—C6—C7	−1.0 (2)	N3—C13—C18—C17	174.77 (13)
C5—C6—C7—C8	−1.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.955 (18)	1.863 (18)	2.6965 (14)	144.3 (15)
N4—H4A···N2^i	0.92 (2)	2.47 (2)	3.2542 (17)	144.1 (16)
N4—H4B···O1^ii	0.93 (2)	2.14 (2)	3.0090 (16)	153.3 (17)
C9—H9···N4^i	1.008 (17)	2.567 (17)	3.571 (2)	173.7 (13)
C11—H11C···N1^iii	0.98 (2)	2.68 (2)	3.5669 (19)	152.0 (16)
C18—H18···N2^iii	0.997 (17)	2.439 (17)	3.3984 (18)	161.2 (13)

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