2-Amino-4-(2-chloro­phen­yl)-7,7-dimethyl-1-(4-methyl­phen­yl)-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carbonitrile

The title compound, C₂₅H₂₄ClN₃O, was synthesized by the reaction of 2-chloro­phenyl­methyl­idenemalononitrile and 3-(4-tolyl­amino)-5,5-dimethyl­cyclo­hex-2-enone in the presence of triethyl­benzyl­ammonium chloride in an aqueous medium. All bond lengths and angles are normal. In the crystal structure, inter­molecular N—H...O hydrogen bonds link the mol­ecules into chains extending in the [101] direction.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.029
• wR factor = 0.076
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2A    ...          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.34
           From the CIF: _reflns_number_total               3434
           Count of symmetry unique reflns         1956
           Completeness (_total/calc)            175.56%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1478
           Fraction of Friedel pairs measured     0.756
           Are heavy atom types Z>Si present        yes

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

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

2-Amino-4-(2-chlorophenyl)-7,7-dimethyl-1-(4-methylphenyl)-5-oxo- 1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile

Crystal data

C25H24ClN3O	F(000) = 880
Mr = 417.92	Dx = 1.290 Mg m^−3
Monoclinic, Cc	Melting point = 525–527 K
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71070 Å
a = 19.541 (2) Å	Cell parameters from 4284 reflections
b = 9.0199 (8) Å	θ = 3.3–25.3°
c = 14.8424 (16) Å	µ = 0.20 mm^−1
β = 124.628 (2)°	T = 173 K
V = 2152.7 (4) Å^3	Block, yellow
Z = 4	0.59 × 0.50 × 0.30 mm

Data collection

Rigaku Mercury diffractometer	3434 independent reflections
Radiation source: fine-focus sealed tube	3389 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
Detector resolution: 7.31 pixels mm^-1	θmax = 25.3°, θmin = 3.3°
ω scans	h = −23→21
Absorption correction: multi-scan (Jacobson, 1998)	k = −10→10
Tmin = 0.892, Tmax = 0.943	l = −15→17
10014 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.029	H-atom parameters constrained
wR(F^2) = 0.076	w = 1/[σ^2(Fo^2) + (0.0474P)^2 + 0.7163P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3434 reflections	Δρmax = 0.20 e Å^−3
275 parameters	Δρmin = −0.22 e Å^−3
2 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (5)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
Cl1	0.11182 (3)	0.63285 (6)	0.52440 (4)	0.04007 (14)
O1	0.16847 (7)	0.89011 (14)	0.38735 (10)	0.0276 (3)
N1	0.43998 (9)	0.69136 (15)	0.57710 (11)	0.0223 (3)
N2	0.49479 (9)	0.52581 (16)	0.72348 (12)	0.0271 (3)
H2A	0.4908	0.4697	0.7688	0.033*
H2B	0.5418	0.5294	0.7283	0.033*
N3	0.34240 (10)	0.46284 (19)	0.77399 (13)	0.0330 (4)
C1	0.42815 (10)	0.60712 (18)	0.64575 (14)	0.0213 (4)
C2	0.35368 (10)	0.60707 (18)	0.63348 (13)	0.0212 (4)
C3	0.27622 (10)	0.68359 (19)	0.53900 (13)	0.0208 (3)
H3	0.2501	0.7414	0.5695	0.025*
C4	0.30222 (10)	0.79093 (19)	0.48522 (14)	0.0209 (3)
C5	0.37797 (10)	0.78864 (18)	0.50187 (14)	0.0207 (3)
C6	0.34704 (10)	0.5277 (2)	0.71020 (14)	0.0233 (4)
C7	0.23899 (10)	0.89547 (18)	0.40799 (13)	0.0222 (4)
C8	0.26021 (12)	1.0085 (2)	0.35351 (16)	0.0291 (4)
H8A	0.2327	1.1031	0.3491	0.035*
H8B	0.2366	0.9754	0.2776	0.035*
C9	0.35307 (11)	1.03799 (19)	0.41000 (15)	0.0266 (4)
C10	0.39848 (12)	0.88811 (19)	0.43857 (16)	0.0272 (4)
H10A	0.3828	0.8376	0.3701	0.033*
H10B	0.4592	0.9058	0.4826	0.033*
C11	0.36675 (14)	1.1220 (2)	0.33161 (18)	0.0382 (5)
H11A	0.4264	1.1393	0.3674	0.057*
H11B	0.3376	1.2174	0.3123	0.057*
H11C	0.3450	1.0631	0.2651	0.057*
C12	0.38838 (13)	1.1305 (2)	0.51343 (18)	0.0365 (5)
H12A	0.3811	1.0772	0.5649	0.055*
H12B	0.3590	1.2256	0.4944	0.055*
H12C	0.4477	1.1482	0.5474	0.055*
C13	0.21269 (10)	0.57131 (18)	0.45663 (13)	0.0212 (4)
C14	0.22888 (12)	0.49432 (19)	0.38891 (15)	0.0263 (4)
H14	0.2791	0.5130	0.3947	0.032*
C15	0.17322 (13)	0.3916 (2)	0.31366 (15)	0.0325 (4)
H15	0.1850	0.3416	0.2676	0.039*
C16	0.10035 (13)	0.3613 (2)	0.30533 (16)	0.0366 (5)
H16	0.0627	0.2892	0.2545	0.044*
C17	0.08261 (13)	0.4354 (2)	0.37049 (17)	0.0357 (5)
H17	0.0326	0.4151	0.3649	0.043*
C18	0.13823 (11)	0.5404 (2)	0.44477 (14)	0.0269 (4)
C19	0.51664 (10)	0.67763 (18)	0.58396 (13)	0.0207 (3)
C20	0.58113 (11)	0.77590 (18)	0.64816 (14)	0.0243 (4)
H20	0.5770	0.8466	0.6923	0.029*
C21	0.65187 (11)	0.77038 (19)	0.64761 (15)	0.0268 (4)
H21	0.6958	0.8388	0.6908	0.032*
C22	0.65938 (11)	0.6666 (2)	0.58493 (14)	0.0250 (4)
C23	0.59529 (11)	0.5653 (2)	0.52389 (15)	0.0276 (4)
H23	0.6004	0.4914	0.4825	0.033*
C24	0.52368 (11)	0.5712 (2)	0.52293 (15)	0.0270 (4)
H24	0.4799	0.5022	0.4805	0.032*
C25	0.73520 (12)	0.6641 (2)	0.58194 (17)	0.0321 (4)
H25A	0.7829	0.7043	0.6507	0.048*
H25B	0.7249	0.7246	0.5205	0.048*
H25C	0.7471	0.5618	0.5727	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0313 (3)	0.0516 (3)	0.0494 (3)	−0.0052 (2)	0.0301 (2)	−0.0061 (2)
O1	0.0176 (7)	0.0309 (7)	0.0307 (7)	0.0029 (5)	0.0116 (6)	0.0000 (5)
N1	0.0177 (7)	0.0240 (7)	0.0266 (8)	0.0014 (6)	0.0134 (6)	0.0045 (6)
N2	0.0180 (8)	0.0337 (8)	0.0284 (8)	0.0016 (6)	0.0125 (7)	0.0097 (6)
N3	0.0262 (9)	0.0442 (9)	0.0279 (9)	−0.0045 (7)	0.0149 (7)	0.0042 (7)
C1	0.0179 (9)	0.0228 (8)	0.0210 (9)	−0.0010 (6)	0.0098 (7)	0.0001 (6)
C2	0.0177 (8)	0.0243 (8)	0.0208 (8)	−0.0017 (7)	0.0104 (7)	0.0007 (6)
C3	0.0159 (8)	0.0244 (9)	0.0212 (9)	0.0009 (6)	0.0100 (7)	−0.0002 (6)
C4	0.0200 (9)	0.0197 (8)	0.0221 (8)	−0.0009 (6)	0.0113 (7)	−0.0009 (6)
C5	0.0205 (9)	0.0187 (8)	0.0238 (9)	0.0003 (6)	0.0132 (7)	0.0003 (6)
C6	0.0159 (8)	0.0292 (9)	0.0217 (9)	−0.0032 (6)	0.0089 (7)	−0.0019 (7)
C7	0.0196 (9)	0.0219 (8)	0.0223 (9)	0.0002 (6)	0.0102 (8)	−0.0038 (6)
C8	0.0257 (10)	0.0242 (9)	0.0306 (10)	0.0034 (7)	0.0119 (8)	0.0062 (7)
C9	0.0250 (10)	0.0223 (8)	0.0331 (10)	0.0006 (7)	0.0168 (8)	0.0048 (7)
C10	0.0258 (10)	0.0269 (9)	0.0320 (10)	0.0037 (7)	0.0184 (9)	0.0075 (7)
C11	0.0368 (12)	0.0339 (10)	0.0417 (12)	0.0018 (8)	0.0209 (10)	0.0146 (8)
C12	0.0298 (11)	0.0323 (10)	0.0447 (12)	−0.0064 (8)	0.0196 (10)	−0.0038 (8)
C13	0.0178 (9)	0.0217 (8)	0.0216 (9)	0.0008 (6)	0.0097 (7)	0.0047 (6)
C14	0.0284 (10)	0.0251 (8)	0.0254 (9)	0.0045 (7)	0.0154 (8)	0.0047 (7)
C15	0.0440 (12)	0.0217 (9)	0.0279 (10)	0.0051 (8)	0.0182 (9)	0.0043 (7)
C16	0.0354 (12)	0.0269 (9)	0.0289 (10)	−0.0066 (8)	0.0072 (9)	0.0014 (7)
C17	0.0236 (10)	0.0359 (11)	0.0379 (11)	−0.0081 (8)	0.0116 (9)	0.0048 (8)
C18	0.0231 (9)	0.0288 (9)	0.0281 (10)	−0.0003 (7)	0.0141 (8)	0.0033 (7)
C19	0.0158 (9)	0.0240 (8)	0.0255 (9)	0.0028 (6)	0.0136 (7)	0.0048 (7)
C20	0.0254 (9)	0.0224 (8)	0.0291 (9)	−0.0007 (7)	0.0178 (8)	−0.0018 (7)
C21	0.0230 (9)	0.0279 (9)	0.0308 (10)	−0.0040 (7)	0.0160 (8)	−0.0024 (7)
C22	0.0202 (9)	0.0317 (9)	0.0235 (9)	0.0028 (7)	0.0126 (8)	0.0030 (7)
C23	0.0260 (10)	0.0315 (9)	0.0268 (9)	0.0019 (7)	0.0160 (8)	−0.0046 (7)
C24	0.0229 (9)	0.0262 (9)	0.0267 (9)	−0.0028 (7)	0.0110 (8)	−0.0031 (7)
C25	0.0253 (10)	0.0435 (11)	0.0336 (10)	0.0008 (8)	0.0204 (9)	−0.0007 (8)

Geometric parameters (Å, º)

Cl1—C18	1.7468 (19)	C11—H11C	0.9800
O1—C7	1.231 (2)	C12—H12A	0.9800
N1—C1	1.392 (2)	C12—H12B	0.9800
N1—C5	1.396 (2)	C12—H12C	0.9800
N1—C19	1.448 (2)	C13—C18	1.391 (2)
N2—C1	1.363 (2)	C13—C14	1.398 (3)
N2—H2A	0.8800	C14—C15	1.381 (3)
N2—H2B	0.8800	C14—H14	0.9500
N3—C6	1.159 (2)	C15—C16	1.385 (3)
C1—C2	1.360 (2)	C15—H15	0.9500
C2—C6	1.412 (2)	C16—C17	1.373 (3)
C2—C3	1.524 (2)	C16—H16	0.9500
C3—C4	1.514 (2)	C17—C18	1.390 (3)
C3—C13	1.529 (2)	C17—H17	0.9500
C3—H3	1.0000	C19—C24	1.379 (3)
C4—C5	1.355 (2)	C19—C20	1.385 (2)
C4—C7	1.456 (2)	C20—C21	1.388 (2)
C5—C10	1.509 (2)	C20—H20	0.9500
C7—C8	1.499 (3)	C21—C22	1.385 (3)
C8—C9	1.529 (3)	C21—H21	0.9500
C8—H8A	0.9900	C22—C23	1.391 (3)
C8—H8B	0.9900	C22—C25	1.507 (2)
C9—C12	1.525 (3)	C23—C24	1.392 (3)
C9—C11	1.534 (3)	C23—H23	0.9500
C9—C10	1.539 (2)	C24—H24	0.9500
C10—H10A	0.9900	C25—H25A	0.9800
C10—H10B	0.9900	C25—H25B	0.9800
C11—H11A	0.9800	C25—H25C	0.9800
C11—H11B	0.9800
C1—N1—C5	119.95 (14)	H11A—C11—H11C	109.5
C1—N1—C19	119.83 (13)	H11B—C11—H11C	109.5
C5—N1—C19	120.22 (13)	C9—C12—H12A	109.5
C1—N2—H2A	120.0	C9—C12—H12B	109.5
C1—N2—H2B	120.0	H12A—C12—H12B	109.5
H2A—N2—H2B	120.0	C9—C12—H12C	109.5
C2—C1—N2	123.24 (16)	H12A—C12—H12C	109.5
C2—C1—N1	120.82 (15)	H12B—C12—H12C	109.5
N2—C1—N1	115.94 (15)	C18—C13—C14	117.22 (16)
C1—C2—C6	118.28 (15)	C18—C13—C3	123.34 (15)
C1—C2—C3	123.42 (15)	C14—C13—C3	119.44 (15)
C6—C2—C3	118.26 (15)	C15—C14—C13	121.25 (18)
C4—C3—C2	108.62 (14)	C15—C14—H14	119.4
C4—C3—C13	111.42 (14)	C13—C14—H14	119.4
C2—C3—C13	111.50 (14)	C14—C15—C16	120.12 (19)
C4—C3—H3	108.4	C14—C15—H15	119.9
C2—C3—H3	108.4	C16—C15—H15	119.9
C13—C3—H3	108.4	C17—C16—C15	119.97 (18)
C5—C4—C7	120.25 (15)	C17—C16—H16	120.0
C5—C4—C3	123.57 (15)	C15—C16—H16	120.0
C7—C4—C3	116.11 (15)	C16—C17—C18	119.61 (19)
C4—C5—N1	121.15 (15)	C16—C17—H17	120.2
C4—C5—C10	121.77 (15)	C18—C17—H17	120.2
N1—C5—C10	117.06 (15)	C17—C18—C13	121.81 (18)
N3—C6—C2	179.3 (2)	C17—C18—Cl1	117.60 (15)
O1—C7—C4	119.98 (16)	C13—C18—Cl1	120.59 (14)
O1—C7—C8	120.41 (15)	C24—C19—C20	120.41 (15)
C4—C7—C8	119.61 (15)	C24—C19—N1	119.91 (15)
C7—C8—C9	115.37 (15)	C20—C19—N1	119.62 (15)
C7—C8—H8A	108.4	C19—C20—C21	119.53 (15)
C9—C8—H8A	108.4	C19—C20—H20	120.2
C7—C8—H8B	108.4	C21—C20—H20	120.2
C9—C8—H8B	108.4	C22—C21—C20	120.95 (16)
H8A—C8—H8B	107.5	C22—C21—H21	119.5
C12—C9—C8	111.37 (16)	C20—C21—H21	119.5
C12—C9—C11	108.60 (15)	C21—C22—C23	118.78 (16)
C8—C9—C11	109.52 (16)	C21—C22—C25	120.73 (16)
C12—C9—C10	110.07 (15)	C23—C22—C25	120.48 (16)
C8—C9—C10	108.49 (15)	C22—C23—C24	120.62 (16)
C11—C9—C10	108.76 (16)	C22—C23—H23	119.7
C5—C10—C9	112.24 (15)	C24—C23—H23	119.7
C5—C10—H10A	109.2	C19—C24—C23	119.63 (16)
C9—C10—H10A	109.2	C19—C24—H24	120.2
C5—C10—H10B	109.2	C23—C24—H24	120.2
C9—C10—H10B	109.2	C22—C25—H25A	109.5
H10A—C10—H10B	107.9	C22—C25—H25B	109.5
C9—C11—H11A	109.5	H25A—C25—H25B	109.5
C9—C11—H11B	109.5	C22—C25—H25C	109.5
H11A—C11—H11B	109.5	H25A—C25—H25C	109.5
C9—C11—H11C	109.5	H25B—C25—H25C	109.5
C5—N1—C1—C2	6.5 (2)	N1—C5—C10—C9	−148.58 (15)
C19—N1—C1—C2	−173.42 (15)	C12—C9—C10—C5	69.6 (2)
C5—N1—C1—N2	−174.03 (15)	C8—C9—C10—C5	−52.5 (2)
C19—N1—C1—N2	6.0 (2)	C11—C9—C10—C5	−171.54 (15)
N2—C1—C2—C6	4.9 (3)	C4—C3—C13—C18	−130.08 (16)
N1—C1—C2—C6	−175.67 (15)	C2—C3—C13—C18	108.37 (18)
N2—C1—C2—C3	−172.82 (16)	C4—C3—C13—C14	49.9 (2)
N1—C1—C2—C3	6.6 (3)	C2—C3—C13—C14	−71.60 (19)
C1—C2—C3—C4	−16.2 (2)	C18—C13—C14—C15	−0.2 (2)
C6—C2—C3—C4	166.04 (15)	C3—C13—C14—C15	179.78 (15)
C1—C2—C3—C13	106.94 (19)	C13—C14—C15—C16	−1.0 (3)
C6—C2—C3—C13	−70.8 (2)	C14—C15—C16—C17	1.2 (3)
C2—C3—C4—C5	15.2 (2)	C15—C16—C17—C18	−0.2 (3)
C13—C3—C4—C5	−108.05 (19)	C16—C17—C18—C13	−1.1 (3)
C2—C3—C4—C7	−167.93 (14)	C16—C17—C18—Cl1	179.27 (15)
C13—C3—C4—C7	68.86 (18)	C14—C13—C18—C17	1.3 (2)
C7—C4—C5—N1	178.71 (15)	C3—C13—C18—C17	−178.70 (16)
C3—C4—C5—N1	−4.5 (3)	C14—C13—C18—Cl1	−179.12 (13)
C7—C4—C5—C10	−2.7 (2)	C3—C13—C18—Cl1	0.9 (2)
C3—C4—C5—C10	174.13 (16)	C1—N1—C19—C24	87.9 (2)
C1—N1—C5—C4	−7.6 (2)	C5—N1—C19—C24	−92.0 (2)
C19—N1—C5—C4	172.33 (15)	C1—N1—C19—C20	−94.92 (19)
C1—N1—C5—C10	173.69 (15)	C5—N1—C19—C20	85.14 (19)
C19—N1—C5—C10	−6.4 (2)	C24—C19—C20—C21	2.4 (3)
C5—C4—C7—O1	174.84 (16)	N1—C19—C20—C21	−174.72 (15)
C3—C4—C7—O1	−2.2 (2)	C19—C20—C21—C22	−0.9 (3)
C5—C4—C7—C8	−4.7 (2)	C20—C21—C22—C23	−1.3 (3)
C3—C4—C7—C8	178.24 (15)	C20—C21—C22—C25	178.12 (17)
O1—C7—C8—C9	161.36 (16)	C21—C22—C23—C24	2.1 (3)
C4—C7—C8—C9	−19.1 (2)	C25—C22—C23—C24	−177.35 (17)
C7—C8—C9—C12	−74.7 (2)	C20—C19—C24—C23	−1.7 (3)
C7—C8—C9—C11	165.13 (15)	N1—C19—C24—C23	175.47 (15)
C7—C8—C9—C10	46.6 (2)	C22—C23—C24—C19	−0.6 (3)
C4—C5—C10—C9	32.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1^i	0.88	2.36	2.937 (2)	123

Symmetry code: (i) x+1/2, −y+3/2, z+1/2.