2-Chloro-3-(pyrrolidin-1-yl)-1,4-naphtho­quinone

The structure of the title compound, C₁₄H₁₂ClNO₂, (I), comprises essentially planar mol­ecules which crystallize in a monoclinic lattice. C-H...O interactions exist to both naphtho­quinone O atoms and the Cl atom.

S1. Comment

NO COMMENT

S2. Experimental

Crystals of (I) were obtained from Spa Contract Synthesis.

S3. Refinement

All H atoms were included in the refinement, at calculated positions, as riding models with C—H set to 0.95 (Ar—H) and 0.99 Å (CH₂).

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

2-Chloro-3-pyrrolidino-1,4-naphthoquinone

Crystal data

C14H12ClNO2	Dx = 1.462 Mg m^−3
Mr = 261.70	Melting point: 371 - 373 K K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.2926 (6) Å	Cell parameters from 6683 reflections
b = 10.4429 (4) Å	θ = 2.9–27.5°
c = 11.2028 (4) Å	µ = 0.31 mm^−1
β = 115.829 (15)°	T = 150 K
V = 1189.14 (9) Å^3	Prism, red
Z = 4	0.20 × 0.17 × 0.10 mm
F(000) = 544

Data collection

Enraf Nonius KappaCCD area-detector diffractometer	2729 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1779 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.109
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.7°
ϕ and ω scans	h = −14→14
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −13→13
Tmin = 0.940, Tmax = 0.969	l = −14→14
18192 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0635P)^2] where P = (Fo^2 + 2Fc^2)/3
2729 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

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

	x	y	z	Uiso*/Ueq
C1	0.72406 (19)	0.57168 (17)	0.20910 (17)	0.0340 (4)
O1	0.80999 (13)	0.49279 (13)	0.27202 (13)	0.0455 (4)
C2	0.58666 (18)	0.54950 (15)	0.17490 (17)	0.0311 (4)
Cl2	0.55843 (5)	0.39676 (4)	0.21805 (5)	0.04187 (19)
C3	0.48609 (18)	0.63550 (15)	0.10887 (16)	0.0295 (4)
N31	0.36071 (15)	0.62397 (13)	0.09139 (14)	0.0333 (4)
C32	0.24495 (18)	0.69738 (19)	−0.00469 (19)	0.0400 (5)
H321	0.2378	0.6911	−0.0958	0.050*
H322	0.2505	0.7887	0.0208	0.050*
C33	0.1295 (2)	0.6316 (2)	0.0057 (2)	0.0495 (5)
H331	0.0534	0.6902	−0.0198	0.062*
H332	0.1018	0.5540	−0.0505	0.062*
C34	0.1864 (2)	0.5978 (2)	0.1514 (2)	0.0500 (6)
H341	0.1319	0.5330	0.1688	0.062*
H342	0.1948	0.6745	0.2065	0.062*
C35	0.3197 (2)	0.54435 (19)	0.17666 (19)	0.0405 (5)
H351	0.3826	0.5529	0.2713	0.051*
H352	0.3132	0.4530	0.1511	0.051*
C4	0.52273 (18)	0.75446 (16)	0.05398 (16)	0.0312 (4)
O4	0.43884 (13)	0.83136 (11)	−0.01240 (13)	0.0410 (4)
C5	0.6960 (2)	0.88599 (16)	0.03419 (19)	0.0389 (5)
H5	0.6298	0.9448	−0.0189	0.049*
C6	0.8252 (2)	0.90886 (18)	0.0622 (2)	0.0461 (5)
H6	0.8479	0.9830	0.0276	0.058*
C7	0.9229 (2)	0.82417 (19)	0.1408 (2)	0.0476 (5)
H7	1.0123	0.8411	0.1613	0.060*
C8	0.88945 (19)	0.71527 (19)	0.1892 (2)	0.0434 (5)
H8	0.9561	0.6567	0.2421	0.054*
C9	0.75917 (18)	0.69085 (16)	0.16107 (17)	0.0339 (4)
C10	0.66167 (18)	0.77668 (16)	0.08350 (17)	0.0312 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0365 (12)	0.0342 (9)	0.0304 (10)	0.0066 (8)	0.0137 (9)	−0.0013 (8)
O1	0.0406 (8)	0.0440 (7)	0.0480 (8)	0.0154 (6)	0.0156 (7)	0.0106 (6)
C2	0.0383 (11)	0.0274 (9)	0.0292 (9)	0.0021 (8)	0.0162 (8)	0.0017 (7)
Cl2	0.0555 (4)	0.0306 (3)	0.0446 (3)	0.0030 (2)	0.0265 (3)	0.00587 (19)
C3	0.0338 (11)	0.0302 (9)	0.0260 (9)	0.0006 (7)	0.0144 (8)	−0.0036 (7)
N31	0.0307 (9)	0.0378 (8)	0.0313 (8)	0.0018 (6)	0.0133 (7)	−0.0002 (7)
C32	0.0324 (11)	0.0472 (11)	0.0353 (11)	0.0054 (9)	0.0100 (9)	−0.0002 (8)
C33	0.0314 (12)	0.0703 (14)	0.0444 (12)	−0.0009 (10)	0.0143 (10)	−0.0043 (10)
C34	0.0349 (12)	0.0737 (15)	0.0435 (12)	−0.0062 (10)	0.0190 (10)	−0.0048 (11)
C35	0.0379 (12)	0.0514 (12)	0.0348 (10)	−0.0034 (9)	0.0182 (9)	0.0010 (9)
C4	0.0381 (11)	0.0284 (9)	0.0288 (9)	0.0035 (8)	0.0161 (8)	−0.0028 (7)
O4	0.0414 (8)	0.0355 (7)	0.0453 (8)	0.0106 (6)	0.0183 (7)	0.0082 (6)
C5	0.0467 (13)	0.0322 (10)	0.0401 (11)	−0.0013 (8)	0.0210 (10)	−0.0011 (8)
C6	0.0540 (15)	0.0407 (11)	0.0502 (13)	−0.0127 (10)	0.0288 (11)	−0.0071 (9)
C7	0.0376 (13)	0.0502 (12)	0.0579 (14)	−0.0092 (10)	0.0234 (11)	−0.0097 (10)
C8	0.0319 (12)	0.0469 (11)	0.0463 (12)	0.0019 (9)	0.0124 (10)	−0.0047 (9)
C9	0.0355 (12)	0.0344 (9)	0.0323 (10)	0.0013 (8)	0.0151 (9)	−0.0041 (8)
C10	0.0358 (11)	0.0301 (9)	0.0278 (9)	0.0003 (8)	0.0140 (8)	−0.0039 (7)

Geometric parameters (Å, º)

C1—O1	1.233 (2)	C34—H341	0.9900
C1—C2	1.446 (3)	C34—H342	0.9900
C1—C9	1.477 (3)	C35—H351	0.9900
C2—C3	1.383 (2)	C35—H352	0.9900
C2—Cl2	1.7361 (17)	C4—O4	1.217 (2)
C3—N31	1.348 (2)	C4—C10	1.474 (3)
C3—C4	1.521 (2)	C5—C6	1.373 (3)
N31—C35	1.484 (2)	C5—C10	1.395 (3)
N31—C32	1.493 (2)	C5—H5	0.9500
C32—C33	1.523 (3)	C6—C7	1.389 (3)
C32—H321	0.9900	C6—H6	0.9500
C32—H322	0.9900	C7—C8	1.381 (3)
C33—C34	1.512 (3)	C7—H7	0.9500
C33—H331	0.9900	C8—C9	1.387 (3)
C33—H332	0.9900	C8—H8	0.9500
C34—C35	1.513 (3)	C9—C10	1.392 (2)
O1—C1—C2	122.06 (17)	H341—C34—H342	109.2
O1—C1—C9	120.12 (18)	N31—C35—C34	103.70 (15)
C2—C1—C9	117.77 (15)	N31—C35—H351	111.0
C3—C2—C1	125.05 (16)	C34—C35—H351	111.0
C3—C2—Cl2	122.55 (15)	N31—C35—H352	111.0
C1—C2—Cl2	112.30 (13)	C34—C35—H352	111.0
N31—C3—C2	125.86 (17)	H351—C35—H352	109.0
N31—C3—C4	117.90 (15)	O4—C4—C10	120.15 (16)
C2—C3—C4	116.23 (16)	O4—C4—C3	120.62 (17)
C3—N31—C35	123.99 (15)	C10—C4—C3	119.22 (15)
C3—N31—C32	126.39 (15)	C6—C5—C10	120.20 (18)
C35—N31—C32	109.33 (15)	C6—C5—H5	119.9
N31—C32—C33	102.90 (15)	C10—C5—H5	119.9
N31—C32—H321	111.2	C5—C6—C7	120.36 (19)
C33—C32—H321	111.2	C5—C6—H6	119.8
N31—C32—H322	111.2	C7—C6—H6	119.8
C33—C32—H322	111.2	C8—C7—C6	119.7 (2)
H321—C32—H322	109.1	C8—C7—H7	120.1
C34—C33—C32	102.27 (16)	C6—C7—H7	120.1
C34—C33—H331	111.3	C7—C8—C9	120.42 (19)
C32—C33—H331	111.3	C7—C8—H8	119.8
C34—C33—H332	111.3	C9—C8—H8	119.8
C32—C33—H332	111.3	C8—C9—C10	119.71 (18)
H331—C33—H332	109.2	C8—C9—C1	119.91 (17)
C33—C34—C35	102.05 (16)	C10—C9—C1	120.34 (17)
C33—C34—H341	111.4	C9—C10—C5	119.58 (18)
C35—C34—H341	111.4	C9—C10—C4	120.93 (16)
C33—C34—H342	111.4	C5—C10—C4	119.49 (16)
C35—C34—H342	111.4
O1—C1—C2—C3	177.58 (17)	N31—C3—C4—C10	173.60 (15)
C9—C1—C2—C3	−5.0 (3)	C2—C3—C4—C10	−5.3 (2)
O1—C1—C2—Cl2	−5.8 (2)	C10—C5—C6—C7	−0.6 (3)
C9—C1—C2—Cl2	171.59 (13)	C5—C6—C7—C8	1.1 (3)
C1—C2—C3—N31	−170.73 (16)	C6—C7—C8—C9	−0.8 (3)
Cl2—C2—C3—N31	13.0 (3)	C7—C8—C9—C10	0.1 (3)
C1—C2—C3—C4	8.0 (3)	C7—C8—C9—C1	177.69 (17)
Cl2—C2—C3—C4	−168.27 (12)	O1—C1—C9—C8	−1.4 (3)
C2—C3—N31—C35	22.3 (3)	C2—C1—C9—C8	−178.79 (16)
C4—C3—N31—C35	−156.50 (16)	O1—C1—C9—C10	176.27 (16)
C2—C3—N31—C32	−164.55 (17)	C2—C1—C9—C10	−1.2 (2)
C4—C3—N31—C32	16.7 (2)	C8—C9—C10—C5	0.4 (3)
C3—N31—C32—C33	172.23 (16)	C1—C9—C10—C5	−177.22 (16)
C35—N31—C32—C33	−13.74 (19)	C8—C9—C10—C4	−178.88 (16)
N31—C32—C33—C34	35.81 (19)	C1—C9—C10—C4	3.5 (3)
C32—C33—C34—C35	−44.7 (2)	C6—C5—C10—C9	−0.1 (3)
C3—N31—C35—C34	160.45 (16)	C6—C5—C10—C4	179.19 (16)
C32—N31—C35—C34	−13.76 (19)	O4—C4—C10—C9	178.93 (16)
C33—C34—C35—N31	35.9 (2)	C3—C4—C10—C9	−0.3 (2)
N31—C3—C4—O4	−5.6 (2)	O4—C4—C10—C5	−0.4 (3)
C2—C3—C4—O4	175.52 (16)	C3—C4—C10—C5	−179.58 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4^i	0.95	2.53	3.281 (2)	136
C7—H7···O1^ii	0.95	2.41	3.254 (2)	149
C35—H351···O4^iii	0.99	2.53	3.398 (2)	146
C35—H352···Cl2	0.99	2.60	2.961 (2)	101

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