4-Bromo-N-(3-thienylmeth­yl)-1,8-naphthalimide

The title compound, C₁₇H₁₀BrNO₂S, is a new fluorescent 1,8-naphthalimide derivative. The thio­phene ring is disordered over two positions. The dihedral angle between the major disorder component of the thio­phene ring and the plane of the naphthalimide is 76.1 (4)°. π–π Stacking inter­actions stabilize the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.051
• wR factor = 0.144
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        S1'

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.06
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C14'
PLAT301_ALERT_3_C Main Residue  Disorder .........................      19.00 Perc.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       3.20 Deg.
              C13  -C17  -C13'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       2.70 Deg.
              H17A -C17  -H17C    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       2.70 Deg.
              H17B -C17  -H17D    1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 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
   7 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

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Computing details

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

4-Bromo-N-(3-thienylmethyl)-1,8-naphthalimide

Crystal data

C17H10BrNO2S	F(000) = 744
Mr = 372.23	Dx = 1.697 Mg m^−3
Monoclinic, P21/c	Melting point: 468 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71070 Å
a = 11.4000 (16) Å	Cell parameters from 2957 reflections
b = 7.2252 (12) Å	θ = 1.8–27.8°
c = 18.211 (2) Å	µ = 2.97 mm^−1
β = 103.721 (6)°	T = 294 K
V = 1457.2 (4) Å^3	Platelet, colourless
Z = 4	0.24 × 0.16 × 0.10 mm

Data collection

Rigaku Saturn diffractometer	3445 independent reflections
Radiation source: rotating anode	1897 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.047
Detector resolution: 7.31 pixels mm^-1	θmax = 27.8°, θmin = 1.8°
ω scans	h = −14→14
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −9→9
Tmin = 0.536, Tmax = 0.756	l = −23→23
13117 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0725P)^2] where P = (Fo^2 + 2Fc^2)/3
3445 reflections	(Δ/σ)max = 0.001
245 parameters	Δρmax = 1.00 e Å^−3
145 restraints	Δρmin = −0.49 e Å^−3

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	Occ. (<1)
Br1	0.70639 (4)	0.39106 (6)	−0.09228 (3)	0.0747 (2)
O1	0.1568 (3)	0.1254 (4)	−0.03356 (17)	0.0746 (9)
O2	0.3749 (3)	0.0836 (4)	0.20873 (16)	0.0748 (9)
N1	0.2665 (3)	0.1027 (4)	0.08753 (17)	0.0510 (8)
C1	0.2555 (4)	0.1378 (5)	0.0107 (2)	0.0517 (10)
C2	0.3652 (3)	0.1942 (5)	−0.01211 (19)	0.0449 (8)
C3	0.3606 (4)	0.2288 (5)	−0.0870 (2)	0.0584 (10)
H3A	0.2881	0.2139	−0.1228	0.070*
C4	0.4635 (4)	0.2861 (5)	−0.1101 (2)	0.0583 (10)
H4A	0.4587	0.3085	−0.1610	0.070*
C5	0.5701 (4)	0.3091 (5)	−0.0587 (2)	0.0550 (10)
C6	0.5814 (3)	0.2746 (4)	0.0202 (2)	0.0473 (9)
C7	0.4758 (3)	0.2166 (4)	0.04166 (19)	0.0430 (8)
C8	0.4816 (3)	0.1816 (5)	0.1187 (2)	0.0458 (8)
C9	0.5880 (4)	0.2066 (6)	0.1719 (2)	0.0602 (10)
H9A	0.5908	0.1846	0.2226	0.072*
C10	0.6917 (4)	0.2647 (5)	0.1507 (2)	0.0676 (12)
H10A	0.7631	0.2817	0.1873	0.081*
C11	0.6891 (3)	0.2967 (5)	0.0765 (2)	0.0585 (10)
H11A	0.7592	0.3335	0.0629	0.070*
C12	0.3743 (4)	0.1190 (5)	0.1427 (2)	0.0528 (10)
C17	0.1560 (3)	0.0561 (6)	0.1127 (2)	0.0622 (11)
H17A	0.1747	−0.0347	0.1523	0.075*	0.594 (6)
H17B	0.0969	0.0045	0.0712	0.075*	0.594 (6)
H17C	0.1754	−0.0299	0.1540	0.075*	0.406 (6)
H17D	0.0985	−0.0012	0.0720	0.075*	0.406 (6)
S1	0.0610 (5)	0.4902 (6)	0.2214 (2)	0.1033 (15)	0.594 (6)
C13	0.1056 (17)	0.2263 (15)	0.1417 (7)	0.0590 (18)	0.594 (6)
C14	0.1384 (11)	0.2956 (13)	0.2111 (8)	0.074 (2)	0.594 (6)
H14	0.1974	0.2432	0.2497	0.089*	0.594 (6)
C15	−0.0044 (16)	0.506 (2)	0.1259 (5)	0.079 (3)	0.594 (6)
H15A	−0.0580	0.5972	0.1027	0.095*	0.594 (6)
C16	0.0349 (11)	0.3639 (14)	0.0905 (7)	0.068 (2)	0.594 (6)
H16A	0.0188	0.3539	0.0381	0.081*	0.594 (6)
S1'	−0.0054 (8)	0.5270 (11)	0.1523 (4)	0.102 (2)	0.406 (6)
C13'	0.101 (3)	0.229 (2)	0.1374 (10)	0.061 (2)	0.406 (6)
C14'	0.0145 (17)	0.339 (2)	0.0995 (10)	0.066 (3)	0.406 (6)
H14B	−0.0299	0.3167	0.0505	0.080*	0.406 (6)
C15'	0.073 (2)	0.428 (2)	0.2347 (8)	0.075 (3)	0.406 (6)
H15B	0.0830	0.4783	0.2828	0.090*	0.406 (6)
C16'	0.1182 (15)	0.2645 (19)	0.2183 (10)	0.067 (3)	0.406 (6)
H16B	0.1568	0.1816	0.2553	0.080*	0.406 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0866 (4)	0.0526 (3)	0.1021 (4)	−0.0024 (2)	0.0567 (3)	−0.0012 (2)
O1	0.0538 (18)	0.097 (2)	0.0665 (18)	−0.0075 (16)	0.0023 (16)	−0.0078 (16)
O2	0.085 (2)	0.090 (2)	0.0524 (17)	0.0014 (17)	0.0222 (16)	0.0142 (15)
N1	0.052 (2)	0.046 (2)	0.057 (2)	0.0000 (14)	0.0188 (17)	0.0031 (14)
C1	0.054 (2)	0.047 (2)	0.054 (2)	−0.0004 (18)	0.013 (2)	−0.0065 (18)
C2	0.056 (2)	0.0346 (19)	0.0457 (19)	0.0036 (17)	0.0143 (18)	−0.0035 (16)
C3	0.066 (3)	0.056 (3)	0.051 (2)	0.008 (2)	0.008 (2)	−0.0019 (19)
C4	0.077 (3)	0.053 (3)	0.051 (2)	0.008 (2)	0.028 (2)	0.0032 (19)
C5	0.071 (3)	0.034 (2)	0.067 (2)	0.0046 (19)	0.030 (2)	−0.0047 (19)
C6	0.056 (2)	0.0300 (19)	0.059 (2)	0.0024 (16)	0.0202 (19)	−0.0040 (17)
C7	0.050 (2)	0.0313 (19)	0.0484 (19)	0.0018 (15)	0.0135 (17)	−0.0054 (15)
C8	0.050 (2)	0.0386 (19)	0.049 (2)	0.0051 (17)	0.0126 (18)	−0.0005 (17)
C9	0.061 (3)	0.060 (3)	0.056 (2)	0.003 (2)	0.008 (2)	−0.002 (2)
C10	0.056 (3)	0.064 (3)	0.071 (3)	0.002 (2)	−0.009 (2)	−0.010 (2)
C11	0.047 (2)	0.052 (2)	0.075 (3)	−0.0025 (19)	0.011 (2)	−0.010 (2)
C12	0.059 (3)	0.043 (2)	0.057 (2)	0.0083 (18)	0.016 (2)	0.0007 (18)
C17	0.060 (3)	0.057 (2)	0.074 (3)	−0.009 (2)	0.027 (2)	0.002 (2)
S1	0.082 (2)	0.106 (3)	0.122 (3)	0.005 (2)	0.024 (2)	−0.051 (2)
C13	0.047 (3)	0.061 (3)	0.075 (3)	−0.011 (3)	0.026 (3)	−0.001 (3)
C14	0.064 (4)	0.082 (4)	0.081 (4)	−0.001 (3)	0.028 (3)	−0.009 (3)
C15	0.052 (4)	0.085 (5)	0.102 (6)	0.002 (4)	0.024 (5)	0.001 (5)
C16	0.046 (4)	0.081 (4)	0.085 (4)	−0.004 (3)	0.035 (3)	0.004 (4)
S1'	0.081 (3)	0.101 (3)	0.132 (5)	0.019 (2)	0.044 (4)	0.002 (3)
C13'	0.049 (4)	0.065 (4)	0.076 (4)	−0.010 (4)	0.027 (4)	−0.003 (4)
C14'	0.045 (5)	0.077 (5)	0.082 (5)	−0.008 (4)	0.026 (4)	0.000 (4)
C15'	0.068 (6)	0.076 (6)	0.083 (5)	−0.009 (5)	0.024 (5)	−0.018 (5)
C16'	0.058 (4)	0.074 (4)	0.076 (4)	−0.008 (4)	0.031 (4)	−0.002 (4)

Geometric parameters (Å, º)

Br1—C5	1.894 (4)	C11—H11A	0.9300
O1—C1	1.223 (5)	C17—C13	1.505 (7)
O2—C12	1.228 (5)	C17—C13'	1.512 (8)
N1—C12	1.396 (5)	C17—H17A	0.9600
N1—C1	1.397 (5)	C17—H17B	0.9600
N1—C17	1.478 (5)	C17—H17C	0.9600
C1—C2	1.466 (5)	C17—H17D	0.9601
C2—C3	1.375 (5)	S1—C14	1.694 (8)
C2—C7	1.410 (5)	S1—C15	1.726 (9)
C3—C4	1.399 (5)	C13—C14	1.328 (8)
C3—H3A	0.9300	C13—C16	1.467 (8)
C4—C5	1.357 (5)	C14—H14	0.9300
C4—H4A	0.9300	C15—C16	1.343 (9)
C5—C6	1.434 (5)	C15—H15A	0.9300
C6—C11	1.410 (5)	C16—H16A	0.9300
C6—C7	1.415 (5)	S1'—C15'	1.710 (10)
C7—C8	1.411 (5)	S1'—C14'	1.711 (9)
C8—C9	1.373 (5)	C13'—C14'	1.328 (9)
C8—C12	1.465 (5)	C13'—C16'	1.463 (9)
C9—C10	1.393 (6)	C14'—H14B	0.9300
C9—H9A	0.9300	C15'—C16'	1.349 (10)
C10—C11	1.363 (5)	C15'—H15B	0.9300
C10—H10A	0.9300	C16'—H16B	0.9300
C12—N1—C1	124.1 (3)	C13—C17—H17A	109.3
C12—N1—C17	117.7 (3)	C13'—C17—H17A	112.1
C1—N1—C17	118.1 (3)	N1—C17—H17B	109.6
O1—C1—N1	119.8 (4)	C13—C17—H17B	109.7
O1—C1—C2	123.2 (4)	C13'—C17—H17B	107.0
N1—C1—C2	117.0 (3)	H17A—C17—H17B	108.3
C3—C2—C7	119.1 (3)	N1—C17—H17C	109.6
C3—C2—C1	119.8 (3)	C13—C17—H17C	106.9
C7—C2—C1	121.1 (3)	C13'—C17—H17C	109.7
C2—C3—C4	121.0 (4)	H17A—C17—H17C	2.7
C2—C3—H3A	119.5	H17B—C17—H17C	110.7
C4—C3—H3A	119.5	N1—C17—H17D	109.6
C5—C4—C3	120.4 (4)	C13—C17—H17D	112.0
C5—C4—H4A	119.8	C13'—C17—H17D	109.3
C3—C4—H4A	119.8	H17A—C17—H17D	106.0
C4—C5—C6	121.5 (4)	H17B—C17—H17D	2.7
C4—C5—Br1	119.0 (3)	H17C—C17—H17D	108.3
C6—C5—Br1	119.5 (3)	C14—S1—C15	93.1 (6)
C11—C6—C7	118.9 (3)	C14—C13—C16	109.7 (7)
C11—C6—C5	124.4 (4)	C14—C13—C17	126.7 (10)
C7—C6—C5	116.6 (3)	C16—C13—C17	121.9 (8)
C2—C7—C8	119.6 (3)	C13—C14—S1	112.5 (7)
C2—C7—C6	121.4 (3)	C13—C14—H14	123.8
C8—C7—C6	119.0 (3)	S1—C14—H14	123.8
C9—C8—C7	120.2 (3)	C16—C15—S1	108.7 (10)
C9—C8—C12	119.3 (3)	C16—C15—H15A	125.7
C7—C8—C12	120.4 (3)	S1—C15—H15A	125.7
C8—C9—C10	120.7 (4)	C15—C16—C13	114.1 (9)
C8—C9—H9A	119.7	C15—C16—H16A	123.0
C10—C9—H9A	119.7	C13—C16—H16A	123.0
C11—C10—C9	120.4 (4)	C15'—S1'—C14'	92.8 (9)
C11—C10—H10A	119.8	C14'—C13'—C16'	108.8 (9)
C9—C10—H10A	119.8	C14'—C13'—C17	130.5 (15)
C10—C11—C6	120.8 (4)	C16'—C13'—C17	118.6 (12)
C10—C11—H11A	119.6	C13'—C14'—S1'	111.4 (9)
C6—C11—H11A	119.6	C13'—C14'—H14B	124.3
O2—C12—N1	119.1 (4)	S1'—C14'—H14B	124.3
O2—C12—C8	123.1 (4)	C16'—C15'—S1'	108.7 (12)
N1—C12—C8	117.7 (3)	C16'—C15'—H15B	125.7
N1—C17—C13	110.3 (7)	S1'—C15'—H15B	125.7
N1—C17—C13'	110.2 (10)	C15'—C16'—C13'	114.2 (11)
C13—C17—C13'	3.2 (14)	C15'—C16'—H16B	122.9
N1—C17—H17A	109.6	C13'—C16'—H16B	122.9
C12—N1—C1—O1	−177.8 (3)	C1—N1—C12—O2	−179.4 (3)
C17—N1—C1—O1	−1.6 (5)	C17—N1—C12—O2	4.3 (5)
C12—N1—C1—C2	0.3 (5)	C1—N1—C12—C8	1.7 (5)
C17—N1—C1—C2	176.6 (3)	C17—N1—C12—C8	−174.6 (3)
O1—C1—C2—C3	−2.6 (6)	C9—C8—C12—O2	−1.5 (6)
N1—C1—C2—C3	179.3 (3)	C7—C8—C12—O2	178.7 (3)
O1—C1—C2—C7	176.4 (3)	C9—C8—C12—N1	177.3 (3)
N1—C1—C2—C7	−1.7 (5)	C7—C8—C12—N1	−2.4 (5)
C7—C2—C3—C4	−0.2 (6)	C12—N1—C17—C13	80.4 (7)
C1—C2—C3—C4	178.8 (3)	C1—N1—C17—C13	−96.1 (7)
C2—C3—C4—C5	−0.2 (6)	C12—N1—C17—C13'	83.8 (10)
C3—C4—C5—C6	0.5 (6)	C1—N1—C17—C13'	−92.7 (10)
C3—C4—C5—Br1	−178.9 (3)	N1—C17—C13—C14	−84.9 (15)
C4—C5—C6—C11	−179.7 (3)	C13'—C17—C13—C14	−174 (31)
Br1—C5—C6—C11	−0.3 (5)	N1—C17—C13—C16	78.7 (15)
C4—C5—C6—C7	−0.4 (5)	C13'—C17—C13—C16	−10 (28)
Br1—C5—C6—C7	179.0 (2)	C16—C13—C14—S1	14.2 (16)
C3—C2—C7—C8	180.0 (3)	C17—C13—C14—S1	179.6 (11)
C1—C2—C7—C8	0.9 (5)	C15—S1—C14—C13	−8.8 (13)
C3—C2—C7—C6	0.4 (5)	C14—S1—C15—C16	0.0 (13)
C1—C2—C7—C6	−178.7 (3)	S1—C15—C16—C13	8.1 (17)
C11—C6—C7—C2	179.3 (3)	C14—C13—C16—C15	−14.7 (18)
C5—C6—C7—C2	−0.1 (5)	C17—C13—C16—C15	179.2 (15)
C11—C6—C7—C8	−0.3 (5)	N1—C17—C13'—C14'	95 (3)
C5—C6—C7—C8	−179.7 (3)	C13—C17—C13'—C14'	−173 (32)
C2—C7—C8—C9	−178.6 (3)	N1—C17—C13'—C16'	−103.3 (18)
C6—C7—C8—C9	1.0 (5)	C13—C17—C13'—C16'	−11 (28)
C2—C7—C8—C12	1.1 (5)	C16'—C13'—C14'—S1'	22 (2)
C6—C7—C8—C12	−179.2 (3)	C17—C13'—C14'—S1'	−175.5 (18)
C7—C8—C9—C10	−0.7 (6)	C15'—S1'—C14'—C13'	−15.9 (19)
C12—C8—C9—C10	179.5 (3)	C14'—S1'—C15'—C16'	4.5 (18)
C8—C9—C10—C11	−0.3 (6)	S1'—C15'—C16'—C13'	7 (2)
C9—C10—C11—C6	1.0 (6)	C14'—C13'—C16'—C15'	−19 (3)
C7—C6—C11—C10	−0.7 (5)	C17—C13'—C16'—C15'	176 (2)
C5—C6—C11—C10	178.6 (3)