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

The structure of the title compound, C₁₄H₁₂ClNO₃, (I), comprises essentially planar mol­ecules stacked parallel to the a axis. C-H...O hydrogen-bonding interactions exist to both naphtho­quinone O atoms and the Cl atom, but not to the morpholine O atom.

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.

2-Chloro-3-(4-morpholino)-1,4-naphthoquinone

Crystal data

C14H12ClNO3	F(000) = 288
Mr = 277.70	Dx = 1.518 Mg m^−3
Triclinic, P1	Melting point: 428 - 430 K K
a = 5.0386 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3948 (2) Å	Cell parameters from 4135 reflections
c = 12.7421 (3) Å	θ = 2.9–27.5°
α = 67.2038 (12)°	µ = 0.32 mm^−1
β = 84.4066 (10)°	T = 150 K
γ = 81.2678 (12)°	Plate, red
V = 607.56 (2) Å^3	0.40 × 0.20 × 0.08 mm
Z = 2

Data collection

Enraf Nonius KappaCCD area-detector diffractometer	2761 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2449 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
φ and ω scans	h = −6→6
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −13→13
Tmin = 0.884, Tmax = 0.977	l = −15→16
6621 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
2761 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.37 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	0.5044 (3)	0.20176 (14)	0.10486 (11)	0.0230 (3)
O1	0.4184 (2)	0.28268 (11)	0.01277 (9)	0.0345 (3)
C2	0.4346 (3)	0.05762 (14)	0.15913 (11)	0.0209 (3)
Cl2	0.20776 (6)	0.01615 (3)	0.08691 (3)	0.02830 (17)
C3	0.5264 (2)	−0.03813 (13)	0.26084 (11)	0.0203 (3)
N31	0.4885 (2)	−0.17681 (12)	0.30333 (10)	0.0247 (3)
C32	0.4332 (3)	−0.26062 (15)	0.42384 (12)	0.0280 (3)
H111	0.3748	−0.1981	0.4661	0.035*
H112	0.5974	−0.3226	0.4581	0.035*
C33	0.2117 (3)	−0.34858 (15)	0.43056 (13)	0.0329 (3)
H121	0.1748	−0.4083	0.5112	0.041*
H122	0.0451	−0.2853	0.4012	0.041*
O34	0.2832 (2)	−0.43609 (10)	0.36633 (9)	0.0344 (3)
C35	0.3313 (3)	−0.35325 (15)	0.24931 (13)	0.0303 (3)
H131	0.1645	−0.2919	0.2177	0.038*
H132	0.3831	−0.4156	0.2065	0.038*
C36	0.5524 (3)	−0.26367 (14)	0.23482 (12)	0.0244 (3)
H141	0.7240	−0.3250	0.2586	0.030*
H142	0.5746	−0.2023	0.1535	0.030*
C4	0.6912 (3)	0.01070 (14)	0.32853 (12)	0.0230 (3)
O4	0.7648 (3)	−0.06883 (11)	0.42194 (10)	0.0419 (3)
C5	0.9383 (3)	0.19717 (14)	0.33317 (12)	0.0242 (3)
H5	0.9982	0.1350	0.4061	0.030*
C6	1.0187 (3)	0.33047 (15)	0.28378 (13)	0.0293 (3)
H6	1.1341	0.3596	0.3227	0.037*
C7	0.9300 (3)	0.42136 (14)	0.17709 (13)	0.0304 (3)
H7	0.9838	0.5129	0.1438	0.038*
C8	0.7641 (3)	0.37966 (14)	0.11893 (12)	0.0274 (3)
H8	0.7053	0.4422	0.0459	0.034*
C9	0.6838 (3)	0.24580 (13)	0.16766 (11)	0.0203 (3)
C10	0.7691 (3)	0.15463 (13)	0.27548 (11)	0.0206 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0255 (7)	0.0223 (7)	0.0224 (7)	0.0005 (5)	−0.0045 (5)	−0.0100 (5)
O1	0.0511 (7)	0.0251 (5)	0.0262 (6)	−0.0009 (5)	−0.0165 (5)	−0.0064 (4)
C2	0.0199 (6)	0.0245 (6)	0.0225 (7)	−0.0037 (5)	−0.0035 (5)	−0.0124 (5)
Cl2	0.0250 (2)	0.0357 (3)	0.0301 (3)	−0.00578 (16)	−0.00844 (16)	−0.01645 (18)
C3	0.0202 (6)	0.0223 (6)	0.0212 (7)	−0.0059 (5)	−0.0001 (5)	−0.0103 (5)
N31	0.0335 (7)	0.0221 (6)	0.0221 (6)	−0.0111 (5)	0.0015 (5)	−0.0101 (5)
C32	0.0349 (8)	0.0251 (7)	0.0240 (7)	−0.0115 (6)	0.0004 (6)	−0.0070 (6)
C33	0.0363 (8)	0.0305 (8)	0.0325 (8)	−0.0139 (6)	0.0072 (6)	−0.0109 (6)
O34	0.0421 (6)	0.0267 (5)	0.0379 (6)	−0.0167 (5)	0.0042 (5)	−0.0129 (5)
C35	0.0319 (7)	0.0291 (7)	0.0357 (8)	−0.0140 (6)	0.0003 (6)	−0.0152 (6)
C36	0.0248 (7)	0.0241 (6)	0.0290 (7)	−0.0080 (5)	0.0010 (5)	−0.0138 (6)
C4	0.0274 (7)	0.0198 (6)	0.0229 (7)	−0.0038 (5)	−0.0065 (5)	−0.0078 (5)
O4	0.0642 (8)	0.0265 (6)	0.0332 (6)	−0.0144 (5)	−0.0259 (6)	−0.0006 (5)
C5	0.0280 (7)	0.0243 (6)	0.0239 (7)	−0.0047 (5)	−0.0044 (5)	−0.0119 (6)
C6	0.0313 (7)	0.0303 (7)	0.0335 (8)	−0.0102 (6)	−0.0014 (6)	−0.0176 (6)
C7	0.0372 (8)	0.0225 (7)	0.0355 (8)	−0.0117 (6)	0.0024 (6)	−0.0135 (6)
C8	0.0327 (7)	0.0228 (7)	0.0253 (7)	−0.0032 (6)	−0.0019 (6)	−0.0075 (6)
C9	0.0230 (6)	0.0185 (6)	0.0213 (6)	−0.0013 (5)	−0.0021 (5)	−0.0097 (5)
C10	0.0229 (7)	0.0187 (6)	0.0219 (7)	−0.0016 (5)	−0.0027 (5)	−0.0094 (5)

Geometric parameters (Å, º)

C1—O1	1.2229 (17)	C35—H131	0.9900
C1—C2	1.4685 (19)	C35—H132	0.9900
C1—C9	1.4892 (17)	C36—H141	0.9900
C2—C3	1.3645 (19)	C36—H142	0.9900
C2—Cl2	1.7322 (12)	C4—O4	1.2116 (18)
C3—N31	1.3661 (16)	C4—C10	1.4806 (18)
C3—C4	1.5160 (17)	C5—C6	1.3875 (19)
N31—C32	1.4657 (18)	C5—C10	1.3968 (17)
N31—C36	1.4658 (15)	C5—H5	0.9500
C32—C33	1.5230 (18)	C6—C7	1.391 (2)
C32—H111	0.9900	C6—H6	0.9500
C32—H112	0.9900	C7—C8	1.384 (2)
C33—O34	1.4307 (16)	C7—H7	0.9500
C33—H121	0.9900	C8—C9	1.3922 (19)
C33—H122	0.9900	C8—H8	0.9500
O34—C35	1.4218 (18)	C9—C10	1.3975 (18)
C35—C36	1.5110 (17)
O1—C1—C2	121.87 (12)	C36—C35—H132	109.5
O1—C1—C9	121.24 (12)	H131—C35—H132	108.1
C2—C1—C9	116.88 (11)	N31—C36—C35	110.60 (10)
C3—C2—C1	124.69 (11)	N31—C36—H141	109.5
C3—C2—Cl2	120.44 (10)	C35—C36—H141	109.5
C1—C2—Cl2	114.82 (10)	N31—C36—H142	109.5
C2—C3—N31	124.03 (11)	C35—C36—H142	109.5
C2—C3—C4	118.06 (11)	H141—C36—H142	108.1
N31—C3—C4	117.85 (12)	O4—C4—C10	121.35 (12)
C3—N31—C32	124.81 (11)	O4—C4—C3	120.22 (12)
C3—N31—C36	121.78 (11)	C10—C4—C3	118.37 (12)
C32—N31—C36	112.39 (11)	C6—C5—C10	119.88 (13)
N31—C32—C33	107.81 (12)	C6—C5—H5	120.1
N31—C32—H111	110.1	C10—C5—H5	120.1
C33—C32—H111	110.1	C5—C6—C7	119.87 (12)
N31—C32—H112	110.1	C5—C6—H6	120.1
C33—C32—H112	110.1	C7—C6—H6	120.1
H111—C32—H112	108.5	C8—C7—C6	120.63 (12)
O34—C33—C32	111.99 (11)	C8—C7—H7	119.7
O34—C33—H121	109.2	C6—C7—H7	119.7
C32—C33—H121	109.2	C7—C8—C9	119.83 (13)
O34—C33—H122	109.2	C7—C8—H8	120.1
C32—C33—H122	109.2	C9—C8—H8	120.1
H121—C33—H122	107.9	C8—C9—C10	119.84 (12)
C35—O34—C33	110.69 (10)	C8—C9—C1	119.58 (12)
O34—C35—C36	110.76 (11)	C10—C9—C1	120.57 (12)
O34—C35—H131	109.5	C5—C10—C9	119.93 (12)
C36—C35—H131	109.5	C5—C10—C4	118.96 (12)
O34—C35—H132	109.5	C9—C10—C4	121.07 (11)
O1—C1—C2—C3	179.13 (13)	C2—C3—C4—C10	−6.58 (19)
C9—C1—C2—C3	−1.4 (2)	N31—C3—C4—C10	170.77 (11)
O1—C1—C2—Cl2	−3.65 (18)	C10—C5—C6—C7	0.2 (2)
C9—C1—C2—Cl2	175.86 (8)	C5—C6—C7—C8	−0.7 (2)
C1—C2—C3—N31	−171.18 (12)	C6—C7—C8—C9	0.3 (2)
Cl2—C2—C3—N31	11.74 (19)	C7—C8—C9—C10	0.5 (2)
C1—C2—C3—C4	6.0 (2)	C7—C8—C9—C1	179.75 (11)
Cl2—C2—C3—C4	−171.09 (9)	O1—C1—C9—C8	−2.6 (2)
C2—C3—N31—C32	−142.17 (14)	C2—C1—C9—C8	177.94 (11)
C4—C3—N31—C32	40.65 (19)	O1—C1—C9—C10	176.66 (12)
C2—C3—N31—C36	50.26 (19)	C2—C1—C9—C10	−2.85 (19)
C4—C3—N31—C36	−126.92 (13)	C6—C5—C10—C9	0.7 (2)
C3—N31—C32—C33	136.77 (13)	C6—C5—C10—C4	178.52 (12)
C36—N31—C32—C33	−54.65 (15)	C8—C9—C10—C5	−1.1 (2)
N31—C32—C33—O34	57.20 (16)	C1—C9—C10—C5	179.73 (11)
C32—C33—O34—C35	−60.29 (16)	C8—C9—C10—C4	−178.81 (12)
C33—O34—C35—C36	58.29 (15)	C1—C9—C10—C4	2.0 (2)
C3—N31—C36—C35	−136.06 (13)	O4—C4—C10—C5	2.2 (2)
C32—N31—C36—C35	54.96 (16)	C3—C4—C10—C5	−175.08 (11)
O34—C35—C36—N31	−55.48 (15)	O4—C4—C10—C9	179.94 (14)
C2—C3—C4—O4	176.14 (13)	C3—C4—C10—C9	2.69 (19)
N31—C3—C4—O4	−6.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4^i	0.95	2.41	3.2914 (18)	155
C33—H122···O4^ii	0.99	2.56	3.3692 (19)	139
C36—H142···Cl2	0.99	2.61	3.1439 (14)	114
C36—H142···O1^iii	0.99	2.56	3.2246 (17)	125

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