1-(p-Chloro­phenyl)-3,4-di­methyl-­5,6,7,8-tetra­hydro­pyrazolo­[3,4-b]­quinoline

The title compound, C₁₈H₁₈ClN₃, shows no unusual features. There is no hydrogen-bonding or π–π stacking.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.128
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

1-(p-Chlorophenyl)-3,4-dimethyl-5,6,7,8-tetrahydropyrazolo[3,4-b]quinoline

Crystal data

C18H18ClN3	F(000) = 656
Mr = 311.80	Dx = 1.379 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.2097 (6) Å	Cell parameters from 3431 reflections
b = 7.5773 (3) Å	θ = 3.4–27.6°
c = 20.6921 (12) Å	µ = 0.25 mm^−1
β = 110.203 (3)°	T = 120 K
V = 1502.29 (14) Å^3	Plate, colourless
Z = 4	0.32 × 0.12 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	3431 independent reflections
Radiation source: fine-focus sealed X-ray tube	2068 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.097
φ scans and ω scans with κ offsets	θmax = 27.6°, θmin = 3.4°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −13→13
Tmin = 0.947, Tmax = 0.987	k = −9→9
22681 measured reflections	l = −26→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0682P)^2] where P = (Fo^2 + 2Fc^2)/3
3431 reflections	(Δ/σ)max = 0.001
220 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl14	1.22307 (6)	0.59681 (8)	0.22896 (3)	0.03141 (19)
N1	0.68101 (18)	0.3536 (2)	0.03180 (9)	0.0226 (4)
N2	0.65961 (19)	0.3644 (2)	−0.03784 (10)	0.0246 (4)
C11	0.8083 (2)	0.4149 (3)	0.07943 (12)	0.0222 (5)
C12	0.8423 (2)	0.3851 (3)	0.14960 (12)	0.0295 (6)
C13	0.9692 (2)	0.4423 (3)	0.19559 (12)	0.0296 (6)
C14	1.0613 (2)	0.5305 (3)	0.17136 (12)	0.0249 (5)
C15	1.0280 (2)	0.5639 (3)	0.10201 (12)	0.0265 (5)
C16	0.9014 (2)	0.5062 (3)	0.05599 (13)	0.0247 (5)
C3	0.5339 (2)	0.3012 (3)	−0.07098 (12)	0.0243 (5)
C31	0.4786 (2)	0.3035 (4)	−0.14761 (12)	0.0305 (6)
C3A	0.4681 (2)	0.2446 (3)	−0.02350 (11)	0.0230 (5)
C4	0.3411 (2)	0.1655 (3)	−0.02711 (12)	0.0229 (5)
C41	0.2379 (2)	0.1071 (3)	−0.09536 (12)	0.0279 (5)
C4A	0.3182 (2)	0.1422 (3)	0.03487 (12)	0.0239 (5)
C5	0.1824 (2)	0.0602 (3)	0.03553 (12)	0.0269 (5)
C6	0.1503 (5)	0.0959 (9)	0.1014 (2)	0.0309 (13)	0.738 (13)
C7	0.2783 (5)	0.0559 (10)	0.1637 (2)	0.0296 (13)	0.738 (13)
C6A	0.1946 (15)	0.002 (3)	0.1091 (6)	0.032 (4)	0.262 (13)
C7A	0.2567 (15)	0.146 (3)	0.1611 (8)	0.033 (4)	0.262 (13)
C8	0.3988 (2)	0.1796 (3)	0.16554 (12)	0.0294 (6)
C8A	0.4218 (2)	0.1931 (3)	0.09756 (12)	0.0235 (5)
N9	0.54664 (18)	0.2602 (3)	0.10215 (9)	0.0236 (4)
C9A	0.5642 (2)	0.2835 (3)	0.04166 (11)	0.0221 (5)
H12	0.7783	0.3253	0.1661	0.035*
H13	0.9927	0.4210	0.2435	0.035*
H15	1.0915	0.6260	0.0859	0.032*
H16	0.8780	0.5291	0.0082	0.030*
H31A	0.5491	0.3530	−0.1647	0.046*
H31B	0.3940	0.3762	−0.1637	0.046*
H31C	0.4561	0.1828	−0.1649	0.046*
H41A	0.1760	0.0170	−0.0877	0.042*
H41B	0.2882	0.0578	−0.1239	0.042*
H41C	0.1823	0.2086	−0.1189	0.042*
H5A	0.1868	−0.0690	0.0295	0.032*	0.738 (13)
H5B	0.1045	0.1063	−0.0043	0.032*	0.738 (13)
H5C	0.1592	−0.0435	0.0045	0.032*	0.262 (13)
H5D	0.1058	0.1470	0.0181	0.032*	0.262 (13)
H6A	0.1231	0.2210	0.1025	0.037*	0.738 (13)
H6B	0.0715	0.0209	0.1022	0.037*	0.738 (13)
H7A	0.3070	−0.0682	0.1617	0.036*	0.738 (13)
H7B	0.2559	0.0712	0.2062	0.036*	0.738 (13)
H6C	0.1008	−0.0285	0.1098	0.038*	0.262 (13)
H6D	0.2538	−0.1046	0.1220	0.038*	0.262 (13)
H7C	0.2006	0.2547	0.1473	0.040*	0.262 (13)
H7D	0.2551	0.1089	0.2068	0.040*	0.262 (13)
H8A	0.3792	0.2988	0.1795	0.035*	0.738 (13)
H8B	0.4857	0.1367	0.2009	0.035*	0.738 (13)
H8C	0.4588	0.0840	0.1928	0.035*	0.262 (13)
H8D	0.4299	0.2913	0.1911	0.035*	0.262 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl14	0.0244 (3)	0.0414 (4)	0.0271 (3)	−0.0059 (3)	0.0072 (2)	−0.0056 (3)
N1	0.0217 (9)	0.0290 (11)	0.0166 (11)	−0.0001 (8)	0.0060 (8)	0.0014 (8)
N2	0.0240 (10)	0.0308 (11)	0.0190 (10)	0.0028 (8)	0.0074 (8)	0.0016 (8)
C11	0.0205 (11)	0.0237 (12)	0.0226 (13)	0.0017 (10)	0.0076 (10)	0.0002 (9)
C12	0.0253 (12)	0.0383 (14)	0.0249 (13)	−0.0052 (11)	0.0087 (10)	0.0056 (11)
C13	0.0278 (12)	0.0403 (15)	0.0197 (13)	−0.0039 (11)	0.0069 (10)	0.0020 (11)
C14	0.0217 (11)	0.0286 (13)	0.0243 (14)	0.0011 (10)	0.0079 (10)	−0.0027 (10)
C15	0.0231 (11)	0.0307 (14)	0.0290 (14)	−0.0015 (10)	0.0132 (10)	0.0010 (10)
C16	0.0241 (11)	0.0288 (13)	0.0227 (13)	0.0016 (10)	0.0100 (10)	0.0005 (10)
C3	0.0239 (11)	0.0262 (12)	0.0225 (13)	0.0047 (10)	0.0076 (10)	0.0016 (10)
C31	0.0279 (12)	0.0417 (15)	0.0212 (13)	0.0017 (11)	0.0076 (10)	0.0002 (11)
C3A	0.0225 (11)	0.0254 (13)	0.0211 (13)	0.0044 (10)	0.0074 (10)	0.0002 (10)
C4	0.0233 (12)	0.0225 (12)	0.0225 (13)	0.0035 (9)	0.0071 (10)	−0.0015 (9)
C41	0.0205 (11)	0.0340 (14)	0.0282 (14)	0.0022 (10)	0.0071 (10)	−0.0055 (11)
C4A	0.0224 (11)	0.0215 (13)	0.0271 (13)	0.0021 (9)	0.0078 (10)	−0.0010 (9)
C5	0.0246 (12)	0.0301 (14)	0.0247 (14)	−0.0040 (10)	0.0068 (10)	−0.0019 (10)
C6	0.023 (2)	0.038 (3)	0.032 (2)	−0.002 (2)	0.0104 (17)	−0.001 (2)
C7	0.027 (2)	0.037 (3)	0.026 (2)	−0.004 (2)	0.0109 (18)	0.001 (2)
C6A	0.023 (6)	0.034 (9)	0.044 (7)	−0.007 (6)	0.018 (5)	−0.003 (6)
C7A	0.038 (7)	0.032 (9)	0.035 (7)	−0.001 (6)	0.020 (6)	−0.006 (7)
C8	0.0274 (12)	0.0382 (14)	0.0220 (13)	−0.0022 (11)	0.0079 (10)	0.0018 (11)
C8A	0.0199 (11)	0.0251 (12)	0.0251 (13)	0.0025 (10)	0.0074 (10)	0.0012 (10)
N9	0.0206 (9)	0.0276 (11)	0.0228 (11)	0.0005 (8)	0.0077 (8)	0.0020 (8)
C9A	0.0203 (11)	0.0230 (12)	0.0226 (13)	0.0028 (9)	0.0070 (9)	0.0012 (9)

Geometric parameters (Å, º)

Cl14—C14	1.744 (2)	C4A—C8A	1.415 (3)
N1—N2	1.383 (3)	C4A—C5	1.524 (3)
N1—C9A	1.384 (3)	C5—C6	1.532 (5)
N1—C11	1.411 (3)	C5—C6A	1.548 (13)
N2—C3	1.319 (3)	C5—H5A	0.99
C11—C12	1.390 (3)	C5—H5B	0.99
C11—C16	1.391 (3)	C5—H5C	0.99
C12—C13	1.386 (3)	C5—H5D	0.99
C12—H12	0.95	C6—C7	1.515 (9)
C13—C14	1.381 (3)	C6—H6A	0.99
C13—H13	0.95	C6—H6B	0.99
C14—C15	1.379 (3)	C7—C8	1.536 (5)
C15—C16	1.385 (3)	C7—H7A	0.99
C15—H15	0.95	C7—H7B	0.99
C16—H16	0.95	C6A—C7A	1.51 (2)
C3—C3A	1.434 (3)	C6A—H6C	0.99
C3—C31	1.488 (3)	C6A—H6D	0.99
C31—H31A	0.98	C7A—C8	1.445 (14)
C31—H31B	0.98	C7A—H7C	0.99
C31—H31C	0.98	C7A—H7D	0.99
C3A—C9A	1.398 (3)	C8—C8A	1.507 (3)
C3A—C4	1.407 (3)	C8—H8A	0.99
C4—C4A	1.392 (3)	C8—H8B	0.99
C4—C41	1.508 (3)	C8—H8C	0.99
C41—H41A	0.98	C8—H8D	0.99
C41—H41B	0.98	C8A—N9	1.345 (3)
C41—H41C	0.98	N9—C9A	1.336 (3)
N2—N1—C9A	110.02 (17)	C6—C5—H5B	108.7
N2—N1—C11	118.96 (17)	H5A—C5—H5B	107.6
C9A—N1—C11	131.00 (19)	C4A—C5—H5C	109.4
C3—N2—N1	107.18 (17)	C6A—C5—H5C	109.4
C12—C11—C16	119.4 (2)	C4A—C5—H5D	109.4
C12—C11—N1	120.91 (19)	C6A—C5—H5D	109.4
C16—C11—N1	119.7 (2)	H5C—C5—H5D	108.0
C13—C12—C11	120.2 (2)	C7—C6—C5	109.5 (5)
C13—C12—H12	119.9	C7—C6—H6A	109.8
C11—C12—H12	119.9	C5—C6—H6A	109.8
C14—C13—C12	119.6 (2)	C7—C6—H6B	109.8
C14—C13—H13	120.2	C5—C6—H6B	109.8
C12—C13—H13	120.2	H6A—C6—H6B	108.2
C15—C14—C13	120.8 (2)	C6—C7—C8	110.3 (5)
C15—C14—Cl14	119.54 (17)	C6—C7—H7A	109.6
C13—C14—Cl14	119.62 (18)	C8—C7—H7A	109.6
C14—C15—C16	119.6 (2)	C6—C7—H7B	109.6
C14—C15—H15	120.2	C8—C7—H7B	109.6
C16—C15—H15	120.2	H7A—C7—H7B	108.1
C15—C16—C11	120.3 (2)	C7A—C6A—C5	111.6 (14)
C15—C16—H16	119.8	C7A—C6A—H6C	109.3
C11—C16—H16	119.8	C5—C6A—H6C	109.3
N2—C3—C3A	110.8 (2)	C7A—C6A—H6D	109.3
N2—C3—C31	119.5 (2)	C5—C6A—H6D	109.3
C3A—C3—C31	129.7 (2)	H6C—C6A—H6D	108.0
C3—C31—H31A	109.5	C8—C7A—C6A	109.9 (13)
C3—C31—H31B	109.5	C8—C7A—H7C	109.7
H31A—C31—H31B	109.5	C6A—C7A—H7C	109.7
C3—C31—H31C	109.5	C8—C7A—H7D	109.7
H31A—C31—H31C	109.5	C6A—C7A—H7D	109.7
H31B—C31—H31C	109.5	H7C—C7A—H7D	108.2
C9A—C3A—C4	117.9 (2)	C7A—C8—C8A	115.4 (6)
C9A—C3A—C3	105.03 (19)	C8A—C8—C7	113.5 (3)
C4—C3A—C3	137.1 (2)	C8A—C8—H8A	108.9
C4A—C4—C3A	116.8 (2)	C7—C8—H8A	108.9
C4A—C4—C41	122.7 (2)	C8A—C8—H8B	108.9
C3A—C4—C41	120.5 (2)	C7—C8—H8B	108.9
C4—C41—H41A	109.5	H8A—C8—H8B	107.7
C4—C41—H41B	109.5	C7A—C8—H8C	108.4
H41A—C41—H41B	109.5	C8A—C8—H8C	108.4
C4—C41—H41C	109.5	C7A—C8—H8D	108.4
H41A—C41—H41C	109.5	C8A—C8—H8D	108.4
H41B—C41—H41C	109.5	H8C—C8—H8D	107.5
C4—C4A—C8A	120.0 (2)	N9—C8A—C4A	123.9 (2)
C4—C4A—C5	120.2 (2)	N9—C8A—C8	114.1 (2)
C8A—C4A—C5	119.8 (2)	C4A—C8A—C8	122.0 (2)
C4A—C5—C6	114.2 (2)	C9A—N9—C8A	114.46 (19)
C4A—C5—C6A	111.1 (4)	N9—C9A—N1	126.2 (2)
C4A—C5—H5A	108.7	N9—C9A—C3A	126.9 (2)
C6—C5—H5A	108.7	N1—C9A—C3A	106.98 (19)
C4A—C5—H5B	108.7
C9A—N1—N2—C3	−0.7 (2)	C4—C4A—C5—C6A	165.1 (8)
C11—N1—N2—C3	−179.32 (19)	C8A—C4A—C5—C6A	−14.3 (9)
N2—N1—C11—C12	−171.2 (2)	C4A—C5—C6—C7	−48.6 (7)
C9A—N1—C11—C12	10.6 (4)	C6A—C5—C6—C7	42.5 (9)
N2—N1—C11—C16	8.7 (3)	C5—C6—C7—C8	63.0 (8)
C9A—N1—C11—C16	−169.6 (2)	C4A—C5—C6A—C7A	48.0 (17)
C16—C11—C12—C13	−1.5 (4)	C6—C5—C6A—C7A	−54.3 (14)
N1—C11—C12—C13	178.4 (2)	C5—C6A—C7A—C8	−65 (2)
C11—C12—C13—C14	0.5 (4)	C6A—C7A—C8—C8A	45.0 (19)
C12—C13—C14—C15	0.7 (4)	C6A—C7A—C8—C7	−47.4 (15)
C12—C13—C14—Cl14	−178.15 (19)	C6—C7—C8—C7A	52.6 (14)
C13—C14—C15—C16	−0.9 (4)	C6—C7—C8—C8A	−47.7 (7)
Cl14—C14—C15—C16	177.93 (18)	C4—C4A—C8A—N9	−2.0 (3)
C14—C15—C16—C11	−0.1 (3)	C5—C4A—C8A—N9	177.4 (2)
C12—C11—C16—C15	1.2 (3)	C4—C4A—C8A—C8	176.6 (2)
N1—C11—C16—C15	−178.6 (2)	C5—C4A—C8A—C8	−3.9 (3)
N1—N2—C3—C3A	−0.5 (2)	C7A—C8—C8A—N9	166.9 (9)
N1—N2—C3—C31	177.2 (2)	C7—C8—C8A—N9	−163.0 (4)
N2—C3—C3A—C9A	1.5 (3)	C7A—C8—C8A—C4A	−11.9 (10)
C31—C3—C3A—C9A	−175.9 (2)	C7—C8—C8A—C4A	18.2 (4)
N2—C3—C3A—C4	−178.2 (3)	C4A—C8A—N9—C9A	3.0 (3)
C31—C3—C3A—C4	4.4 (4)	C8—C8A—N9—C9A	−175.8 (2)
C9A—C3A—C4—C4A	3.7 (3)	C8A—N9—C9A—N1	178.5 (2)
C3—C3A—C4—C4A	−176.5 (2)	C8A—N9—C9A—C3A	−0.5 (3)
C9A—C3A—C4—C41	−175.2 (2)	N2—N1—C9A—N9	−177.5 (2)
C3—C3A—C4—C41	4.5 (4)	C11—N1—C9A—N9	0.9 (4)
C3A—C4—C4A—C8A	−1.5 (3)	N2—N1—C9A—C3A	1.7 (2)
C41—C4—C4A—C8A	177.4 (2)	C11—N1—C9A—C3A	−179.9 (2)
C3A—C4—C4A—C5	179.0 (2)	C4—C3A—C9A—N9	−2.9 (3)
C41—C4—C4A—C5	−2.1 (3)	C3—C3A—C9A—N9	177.3 (2)
C4—C4A—C5—C6	−161.3 (4)	C4—C3A—C9A—N1	177.91 (19)
C8A—C4A—C5—C6	19.3 (4)	C3—C3A—C9A—N1	−1.9 (2)