Di­bromo­methyl- and bromo­methyl- or bromo-substituted ben­zenes and naph­tha­lenes: C—Br...Br inter­actions

The structures of six ben­zene and three naph­tha­lene derivatives involving bromo, bromo­methyl and di­bromo­methyl substituents, namely, 1,3-di­bromo-5-(di­bromo­meth­yl)ben­zene, C₇H₄Br₄, 1,4-di­bromo-2,5-bis­(bromo­meth­yl)ben­zene, C₈H₄Br₆, 1,4-di­bromo-2-(di­bromo­meth­yl)ben­zene, C₇H₄Br₄, 1,2-bis­(di­bromo­meth­yl)ben­zene, C₈H₆Br₄, 1-(bromo­meth­yl)-2-(di­bromo­meth­yl)ben­zene, C₈H₇Br₃, 2-(bromo­meth­yl)-3-(di­bromo­meth­yl)naph­tha­lene, C₁₂H₉Br₃, 2,3-bis­(di­bromo­meth­yl)naph­tha­lene, C₁₂H₈Br₄, 1-(bromo­meth­yl)-2-(di­bromo­meth­yl)naph­tha­lene, C₁₂H₉Br₃, and 1,3-bis­(di­bromo­meth­yl)ben­zene, C₈H₆Br₄, are presented. The packing patterns of these com­pounds are dominated by Br...Br contacts and C—H...Br hydrogen bonds. The Br...Br contacts, shorter than twice the van der Waals radius of bromine (3.7 Å), seem to play a crucial role in the crystal packing of all these com­pounds. The occurrence of Type I and Type II inter­actions is also discussed briefly, considering the effective atomic radius of bromine, as is their impact on the packing of mol­ecules in the individual structures.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2007) for (1); APEX2 (Bruker, 2012) for (2); CrysAlis PRO (Rigaku OD, 2015) for (3), (4), (5), (6), (8), (9); CrysAlis PRO (Agilent, 2012) for (7). Cell refinement: CrysAlis RED (Oxford Diffraction, 2007) for (1); SAINT (Bruker, 2012) for (2); CrysAlis PRO (Rigaku OD, 2015) for (3), (4), (5), (6), (8), (9); CrysAlis PRO (Agilent, 2012) for (7). Data reduction: CrysAlis RED (Oxford Diffraction, 2007) for (1); SAINT (Bruker, 2012) for (2); CrysAlis PRO (Rigaku OD, 2015) for (3), (4), (5), (6), (8), (9); CrysAlis PRO (Agilent, 2012) for (7). For all structures, program(s) used to solve structure: SHELXT (Sheldrick, 2015a). Program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b) for (1), (2); SHELXL2019 (Sheldrick, 2015b) for (3), (4), (5), (6), (7), (8), (9).

1,3-Dibromo-5-(dibromomethyl)benzene (1)

Crystal data

C7H4Br4	F(000) = 1488
Mr = 407.74	Dx = 2.800 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 13.8720 (4) Å	Cell parameters from 13619 reflections
b = 8.8259 (2) Å	θ = 2.6–32.5°
c = 17.2229 (4) Å	µ = 16.58 mm^−1
β = 113.472 (3)°	T = 100 K
V = 1934.17 (9) Å^3	Prism, colourless
Z = 8	0.23 × 0.13 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur S diffractometer	3279 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2626 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 16.1057 pixels mm^-1	θmax = 32.0°, θmin = 2.6°
ω–scan	h = −20→20
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −13→13
Tmin = 0.223, Tmax = 1.000	l = −25→25
25302 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.019	H-atom parameters constrained
wR(F^2) = 0.040	w = 1/[σ^2(Fo^2) + (0.0214P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.001
3279 reflections	Δρmax = 0.62 e Å^−3
100 parameters	Δρmin = −0.79 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.61652 (14)	0.3411 (2)	0.49141 (12)	0.0114 (4)
C2	0.64411 (14)	0.4555 (2)	0.55174 (12)	0.0118 (4)
H2	0.668076	0.432429	0.610311	0.014*
C3	0.63578 (14)	0.6030 (2)	0.52437 (12)	0.0116 (4)
C4	0.60150 (14)	0.6399 (2)	0.43927 (12)	0.0118 (4)
H4	0.596019	0.742745	0.421723	0.014*
C5	0.57543 (14)	0.5235 (2)	0.38041 (12)	0.0111 (4)
C6	0.58299 (14)	0.3733 (2)	0.40601 (11)	0.0116 (4)
H6	0.565410	0.293818	0.365528	0.014*
C7	0.53853 (15)	0.5644 (2)	0.28877 (12)	0.0142 (4)
H7	0.549262	0.675600	0.284409	0.017*
Br1	0.62533 (2)	0.13759 (2)	0.52660 (2)	0.01603 (5)
Br2	0.67295 (2)	0.75894 (2)	0.60630 (2)	0.01647 (5)
Br3	0.61440 (2)	0.45650 (2)	0.23244 (2)	0.01944 (5)
Br4	0.38913 (2)	0.51950 (3)	0.22849 (2)	0.02066 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0114 (8)	0.0106 (9)	0.0136 (9)	0.0003 (7)	0.0065 (7)	0.0019 (7)
C2	0.0101 (8)	0.0159 (10)	0.0091 (8)	−0.0016 (7)	0.0036 (7)	−0.0006 (7)
C3	0.0096 (8)	0.0131 (9)	0.0123 (8)	−0.0038 (7)	0.0046 (7)	−0.0043 (7)
C4	0.0097 (8)	0.0089 (8)	0.0157 (9)	−0.0002 (7)	0.0039 (7)	0.0013 (7)
C5	0.0092 (8)	0.0143 (10)	0.0100 (9)	−0.0010 (7)	0.0040 (7)	0.0009 (7)
C6	0.0128 (8)	0.0116 (9)	0.0106 (8)	−0.0028 (7)	0.0048 (7)	−0.0018 (7)
C7	0.0162 (9)	0.0129 (10)	0.0125 (9)	−0.0029 (8)	0.0046 (7)	0.0008 (7)
Br1	0.02336 (10)	0.01063 (9)	0.01469 (9)	0.00022 (8)	0.00819 (8)	0.00314 (7)
Br2	0.02092 (10)	0.01303 (10)	0.01409 (9)	−0.00382 (8)	0.00553 (8)	−0.00524 (7)
Br3	0.02662 (11)	0.02131 (11)	0.01474 (10)	−0.00250 (8)	0.01284 (8)	0.00021 (8)
Br4	0.01584 (10)	0.02573 (12)	0.01490 (10)	−0.00453 (8)	0.00031 (8)	0.00240 (8)

Geometric parameters (Å, º)

C1—C6	1.384 (2)	C4—H4	0.9500
C1—C2	1.389 (3)	C5—C6	1.388 (3)
C1—Br1	1.8841 (19)	C5—C7	1.497 (3)
C2—C3	1.373 (3)	C6—H6	0.9500
C2—H2	0.9500	C7—Br3	1.941 (2)
C3—C4	1.388 (3)	C7—Br4	1.9535 (19)
C3—Br2	1.8899 (19)	C7—H7	1.0000
C4—C5	1.386 (3)
C6—C1—C2	121.43 (18)	C4—C5—C6	120.72 (17)
C6—C1—Br1	119.27 (15)	C4—C5—C7	118.20 (17)
C2—C1—Br1	119.29 (14)	C6—C5—C7	121.08 (17)
C3—C2—C1	118.15 (17)	C1—C6—C5	118.99 (18)
C3—C2—H2	120.9	C1—C6—H6	120.5
C1—C2—H2	120.9	C5—C6—H6	120.5
C2—C3—C4	122.13 (18)	C5—C7—Br3	112.52 (13)
C2—C3—Br2	118.25 (14)	C5—C7—Br4	110.88 (13)
C4—C3—Br2	119.63 (15)	Br3—C7—Br4	107.85 (9)
C5—C4—C3	118.57 (18)	C5—C7—H7	108.5
C5—C4—H4	120.7	Br3—C7—H7	108.5
C3—C4—H4	120.7	Br4—C7—H7	108.5
C6—C1—C2—C3	1.0 (3)	C2—C1—C6—C5	−1.0 (3)
Br1—C1—C2—C3	−179.22 (13)	Br1—C1—C6—C5	179.21 (14)
C1—C2—C3—C4	−0.3 (3)	C4—C5—C6—C1	0.3 (3)
C1—C2—C3—Br2	179.86 (13)	C7—C5—C6—C1	−179.37 (17)
C2—C3—C4—C5	−0.3 (3)	C4—C5—C7—Br3	129.01 (16)
Br2—C3—C4—C5	179.53 (13)	C6—C5—C7—Br3	−51.3 (2)
C3—C4—C5—C6	0.3 (3)	C4—C5—C7—Br4	−110.11 (17)
C3—C4—C5—C7	180.00 (16)	C6—C5—C7—Br4	69.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Br3^i	0.95	3.16	3.8884 (18)	135
C6—H6···Br4^ii	0.95	3.11	3.9976 (19)	156

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

1,4-Dibromo-2,5-bis(bromomethyl)benzene (2)

Crystal data

C8H4Br6	Z = 1
Mr = 579.57	F(000) = 262
Triclinic, P1	Dx = 3.077 Mg m^−3
a = 4.7187 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.0758 (10) Å	Cell parameters from 9991 reflections
c = 8.3527 (12) Å	θ = 2.5–33.3°
α = 99.836 (6)°	µ = 19.21 mm^−1
β = 92.165 (8)°	T = 100 K
γ = 93.137 (6)°	Plate, colourless
V = 312.79 (8) Å^3	0.23 × 0.16 × 0.02 mm

Data collection

Bruker APEXII CCD area detector diffractometer	2411 independent reflections
Radiation source: fine-focus sealed tube	2240 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
phi and ω scans	θmax = 33.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→7
Tmin = 0.270, Tmax = 0.700	k = −12→12
18782 measured reflections	l = −12→12

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.020	H-atom parameters constrained
wR(F^2) = 0.054	w = 1/[σ^2(Fo^2) + (0.0303P)^2 + 0.2141P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2411 reflections	Δρmax = 1.02 e Å^−3
64 parameters	Δρmin = −0.83 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Br1	0.97547 (4)	0.75420 (2)	0.37834 (2)	0.01197 (5)
Br2	0.46236 (4)	0.03458 (2)	0.24296 (2)	0.01510 (5)
Br3	0.14505 (4)	0.28654 (2)	0.05232 (2)	0.01760 (5)
C1	0.7037 (4)	0.6075 (2)	0.4519 (2)	0.0111 (3)
C2	0.5727 (4)	0.4786 (2)	0.3386 (2)	0.0115 (3)
H2	0.624560	0.464748	0.228519	0.014*
C3	0.3649 (4)	0.3690 (2)	0.3846 (2)	0.0105 (3)
C4	0.2257 (4)	0.2274 (2)	0.2637 (2)	0.0120 (3)
H4	0.040982	0.193184	0.307248	0.014*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01301 (8)	0.01178 (8)	0.01133 (9)	−0.00074 (6)	0.00105 (6)	0.00296 (6)
Br2	0.01625 (9)	0.00975 (8)	0.01826 (10)	0.00050 (6)	0.00076 (7)	−0.00042 (6)
Br3	0.02167 (10)	0.01983 (10)	0.01046 (9)	0.00086 (7)	−0.00383 (7)	0.00141 (7)
C1	0.0112 (6)	0.0101 (6)	0.0119 (7)	0.0007 (5)	0.0015 (6)	0.0020 (6)
C2	0.0120 (7)	0.0121 (7)	0.0099 (7)	0.0007 (5)	0.0000 (6)	0.0010 (6)
C3	0.0106 (6)	0.0107 (6)	0.0098 (7)	0.0016 (5)	0.0004 (5)	0.0007 (5)
C4	0.0128 (7)	0.0128 (7)	0.0098 (7)	0.0006 (5)	−0.0001 (6)	0.0000 (6)

Geometric parameters (Å, º)

Br1—C1	1.8891 (18)	C2—C3	1.394 (2)
Br2—C4	1.9530 (18)	C2—H2	0.9500
Br3—C4	1.9360 (18)	C3—C4	1.494 (2)
C1—C2	1.382 (3)	C4—H4	1.0000
C1—C3^i	1.399 (2)
C2—C1—C3^i	121.45 (16)	C1^i—C3—C4	120.97 (16)
C2—C1—Br1	117.79 (13)	C3—C4—Br3	113.61 (12)
C3^i—C1—Br1	120.76 (13)	C3—C4—Br2	109.46 (12)
C1—C2—C3	120.49 (16)	Br3—C4—Br2	110.24 (9)
C1—C2—H2	119.8	C3—C4—H4	107.8
C3—C2—H2	119.8	Br3—C4—H4	107.8
C2—C3—C1^i	118.06 (16)	Br2—C4—H4	107.8
C2—C3—C4	120.95 (16)
C3^i—C1—C2—C3	0.6 (3)	C2—C3—C4—Br3	−39.6 (2)
Br1—C1—C2—C3	−178.30 (13)	C1^i—C3—C4—Br3	142.25 (14)
C1—C2—C3—C1^i	−0.6 (3)	C2—C3—C4—Br2	84.14 (18)
C1—C2—C3—C4	−178.86 (16)	C1^i—C3—C4—Br2	−94.06 (16)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Br1^i	1.00	2.59	3.1527 (19)	115
C4—H4···Br2^ii	1.00	2.94	3.8308 (18)	149

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

1,4-Dibromo-2-(dibromomethyl)benzene (3)

Crystal data

C7H4Br4	F(000) = 1488
Mr = 407.74	Dx = 2.798 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.1587 (5) Å	Cell parameters from 9209 reflections
b = 7.7779 (1) Å	θ = 3.4–35.5°
c = 13.7815 (4) Å	µ = 16.57 mm^−1
β = 109.503 (3)°	T = 100 K
V = 1935.81 (9) Å^3	Parallelepiped, colourless
Z = 8	0.11 × 0.07 × 0.02 mm

Data collection

SuperNova diffractometer (Agilent Technologies) with Atlas detector	8767 independent reflections
Radiation source: micro-focus sealed X-ray tube	6490 reflections with I > 2σ(I)
Detector resolution: 10.4498 pixels mm^-1	Rint = 0.047
ω scans	θmax = 36.2°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −30→31
Tmin = 0.313, Tmax = 1.000	k = −12→12
28098 measured reflections	l = −22→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.069	w = 1/[σ^2(Fo^2) + (0.0173P)^2 + 1.6927P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.003
8767 reflections	Δρmax = 1.09 e Å^−3
199 parameters	Δρmin = −1.27 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Br11	0.39052 (2)	−0.22999 (4)	0.31582 (3)	0.01599 (7)
Br12	0.59409 (2)	0.46578 (4)	0.43579 (3)	0.01591 (7)
Br13	0.29234 (2)	0.18261 (4)	0.39993 (3)	0.01996 (7)
Br14	0.29610 (2)	0.33656 (4)	0.18859 (3)	0.02193 (8)
C11	0.44837 (18)	−0.0257 (4)	0.3442 (2)	0.0118 (5)
C12	0.41361 (17)	0.1356 (4)	0.3277 (2)	0.0118 (5)
C13	0.45878 (18)	0.2822 (4)	0.3555 (2)	0.0139 (6)
H13	0.436939	0.393279	0.346222	0.017*
C14	0.53413 (17)	0.2655 (4)	0.3959 (2)	0.0125 (6)
C15	0.56862 (18)	0.1050 (4)	0.4105 (2)	0.0142 (6)
H15	0.621031	0.095663	0.437653	0.017*
C16	0.52439 (18)	−0.0410 (4)	0.3844 (2)	0.0141 (6)
H16	0.546603	−0.151698	0.394225	0.017*
C17	0.33157 (18)	0.1498 (4)	0.2864 (2)	0.0147 (6)
H17	0.311275	0.039502	0.250867	0.018*
Br21	0.89440 (2)	0.70008 (4)	0.08853 (2)	0.01416 (6)
Br22	1.10018 (2)	0.01106 (4)	0.14636 (3)	0.01586 (7)
Br23	0.78713 (2)	0.30088 (4)	−0.06853 (2)	0.01756 (7)
Br24	0.80709 (2)	0.12548 (4)	0.14679 (3)	0.02074 (7)
C21	0.95233 (17)	0.4964 (4)	0.1115 (2)	0.0115 (5)
C22	0.91904 (17)	0.3342 (4)	0.1046 (2)	0.0103 (5)
C23	0.96460 (17)	0.1895 (4)	0.1165 (2)	0.0119 (5)
H23	0.943756	0.077671	0.111576	0.014*
C24	1.03977 (18)	0.2083 (4)	0.1353 (2)	0.0123 (5)
C25	1.07282 (17)	0.3698 (4)	0.1441 (2)	0.0126 (6)
H25	1.124637	0.380913	0.157993	0.015*
C26	1.02779 (18)	0.5145 (4)	0.1318 (2)	0.0138 (6)
H26	1.048950	0.626060	0.137339	0.017*
C27	0.83737 (17)	0.3191 (4)	0.0811 (2)	0.0132 (6)
H27	0.819752	0.426693	0.105264	0.016*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br11	0.01949 (16)	0.00967 (12)	0.01860 (16)	−0.00150 (11)	0.00610 (13)	0.00100 (11)
Br12	0.01612 (15)	0.01273 (13)	0.01785 (16)	−0.00257 (11)	0.00431 (12)	0.00018 (11)
Br13	0.01508 (15)	0.01897 (15)	0.02953 (19)	0.00153 (12)	0.01240 (14)	0.00433 (13)
Br14	0.01486 (16)	0.02258 (16)	0.02493 (18)	0.00347 (12)	0.00209 (13)	0.01123 (13)
C11	0.0166 (15)	0.0094 (12)	0.0103 (14)	−0.0005 (10)	0.0059 (12)	0.0021 (10)
C12	0.0113 (13)	0.0105 (12)	0.0133 (14)	0.0005 (10)	0.0039 (11)	−0.0010 (10)
C13	0.0147 (14)	0.0089 (12)	0.0167 (15)	0.0011 (10)	0.0035 (12)	0.0004 (10)
C14	0.0123 (14)	0.0100 (12)	0.0157 (15)	−0.0001 (10)	0.0054 (12)	0.0000 (10)
C15	0.0151 (15)	0.0140 (13)	0.0142 (15)	0.0031 (11)	0.0060 (12)	0.0012 (11)
C16	0.0153 (15)	0.0103 (12)	0.0180 (16)	0.0035 (10)	0.0076 (12)	0.0015 (11)
C17	0.0149 (15)	0.0117 (13)	0.0171 (15)	0.0023 (11)	0.0048 (12)	0.0040 (11)
Br21	0.01618 (15)	0.00934 (12)	0.01850 (15)	0.00178 (10)	0.00783 (12)	0.00137 (10)
Br22	0.01553 (15)	0.01243 (13)	0.01967 (16)	0.00378 (11)	0.00596 (12)	−0.00006 (11)
Br23	0.01471 (15)	0.01882 (15)	0.01580 (15)	0.00300 (11)	0.00065 (12)	0.00241 (11)
Br24	0.01398 (15)	0.02173 (16)	0.02546 (18)	−0.00254 (12)	0.00517 (13)	0.01050 (13)
C21	0.0126 (14)	0.0105 (12)	0.0109 (14)	0.0009 (10)	0.0033 (11)	−0.0004 (10)
C22	0.0110 (13)	0.0092 (12)	0.0110 (13)	0.0000 (9)	0.0040 (11)	0.0005 (10)
C23	0.0133 (14)	0.0101 (12)	0.0114 (13)	−0.0011 (10)	0.0028 (11)	−0.0003 (10)
C24	0.0150 (14)	0.0114 (12)	0.0105 (13)	0.0023 (10)	0.0042 (11)	0.0006 (10)
C25	0.0114 (14)	0.0141 (13)	0.0129 (14)	−0.0002 (10)	0.0047 (11)	−0.0010 (11)
C26	0.0140 (15)	0.0096 (12)	0.0170 (15)	−0.0021 (10)	0.0041 (12)	0.0002 (10)
C27	0.0121 (14)	0.0131 (13)	0.0147 (15)	0.0000 (10)	0.0049 (12)	0.0018 (11)

Geometric parameters (Å, º)

Br11—C11	1.902 (3)	Br21—C21	1.899 (3)
Br12—C14	1.904 (3)	Br22—C24	1.897 (3)
Br13—C17	1.965 (3)	Br23—C27	1.969 (3)
Br14—C17	1.944 (3)	Br24—C27	1.943 (3)
C11—C16	1.380 (4)	C21—C26	1.385 (4)
C11—C12	1.403 (4)	C21—C22	1.402 (4)
C12—C13	1.405 (4)	C22—C23	1.400 (4)
C12—C17	1.486 (4)	C22—C27	1.493 (4)
C13—C14	1.369 (4)	C23—C24	1.383 (4)
C13—H13	0.9500	C23—H23	0.9500
C14—C15	1.396 (4)	C24—C25	1.393 (4)
C15—C16	1.390 (4)	C25—C26	1.394 (4)
C15—H15	0.9500	C25—H25	0.9500
C16—H16	0.9500	C26—H26	0.9500
C17—H17	1.0000	C27—H27	1.0000
C16—C11—C12	121.5 (3)	C26—C21—C22	121.7 (3)
C16—C11—Br11	118.4 (2)	C26—C21—Br21	117.5 (2)
C12—C11—Br11	120.1 (2)	C22—C21—Br21	120.8 (2)
C11—C12—C13	117.7 (3)	C23—C22—C21	117.6 (3)
C11—C12—C17	120.8 (3)	C23—C22—C27	121.9 (3)
C13—C12—C17	121.4 (3)	C21—C22—C27	120.4 (3)
C14—C13—C12	120.3 (3)	C24—C23—C22	120.4 (3)
C14—C13—H13	119.9	C24—C23—H23	119.8
C12—C13—H13	119.9	C22—C23—H23	119.8
C13—C14—C15	121.8 (3)	C23—C24—C25	121.8 (3)
C13—C14—Br12	119.5 (2)	C23—C24—Br22	119.9 (2)
C15—C14—Br12	118.6 (2)	C25—C24—Br22	118.3 (2)
C16—C15—C14	118.4 (3)	C24—C25—C26	118.2 (3)
C16—C15—H15	120.8	C24—C25—H25	120.9
C14—C15—H15	120.8	C26—C25—H25	120.9
C11—C16—C15	120.3 (3)	C21—C26—C25	120.3 (3)
C11—C16—H16	119.9	C21—C26—H26	119.8
C15—C16—H16	119.9	C25—C26—H26	119.8
C12—C17—Br14	113.6 (2)	C22—C27—Br24	114.5 (2)
C12—C17—Br13	110.0 (2)	C22—C27—Br23	110.1 (2)
Br14—C17—Br13	108.49 (15)	Br24—C27—Br23	108.34 (15)
C12—C17—H17	108.2	C22—C27—H27	107.9
Br14—C17—H17	108.2	Br24—C27—H27	107.9
Br13—C17—H17	108.2	Br23—C27—H27	107.9
C16—C11—C12—C13	−1.3 (5)	C26—C21—C22—C23	−1.6 (5)
Br11—C11—C12—C13	176.4 (2)	Br21—C21—C22—C23	176.3 (2)
C16—C11—C12—C17	−178.7 (3)	C26—C21—C22—C27	−179.1 (3)
Br11—C11—C12—C17	−1.0 (4)	Br21—C21—C22—C27	−1.2 (4)
C11—C12—C13—C14	0.8 (5)	C21—C22—C23—C24	0.7 (4)
C17—C12—C13—C14	178.3 (3)	C27—C22—C23—C24	178.1 (3)
C12—C13—C14—C15	0.3 (5)	C22—C23—C24—C25	0.6 (5)
C12—C13—C14—Br12	−178.7 (2)	C22—C23—C24—Br22	−177.8 (2)
C13—C14—C15—C16	−1.0 (5)	C23—C24—C25—C26	−0.9 (4)
Br12—C14—C15—C16	177.9 (2)	Br22—C24—C25—C26	177.4 (2)
C12—C11—C16—C15	0.6 (5)	C22—C21—C26—C25	1.2 (5)
Br11—C11—C16—C15	−177.1 (2)	Br21—C21—C26—C25	−176.7 (2)
C14—C15—C16—C11	0.6 (5)	C24—C25—C26—C21	0.0 (5)
C11—C12—C17—Br14	−141.1 (3)	C23—C22—C27—Br24	35.9 (4)
C13—C12—C17—Br14	41.6 (4)	C21—C22—C27—Br24	−146.7 (2)
C11—C12—C17—Br13	97.1 (3)	C23—C22—C27—Br23	−86.4 (3)
C13—C12—C17—Br13	−80.3 (3)	C21—C22—C27—Br23	91.0 (3)

1,2-Bis(dibromomethyl)benzene (4)

Crystal data

C8H6Br4	Z = 2
Mr = 421.77	F(000) = 388
Triclinic, P1	Dx = 2.687 Mg m^−3
a = 6.9650 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6186 (10) Å	Cell parameters from 2078 reflections
c = 10.4619 (12) Å	θ = 3.8–32.7°
α = 108.632 (11)°	µ = 15.38 mm^−1
β = 97.171 (7)°	T = 200 K
γ = 90.297 (7)°	Plate, colourless
V = 521.34 (10) Å^3	0.60 × 0.16 × 0.04 mm

Data collection

SuperNova diffractometer (Agilent Technologies) with Atlas detector	7277 independent reflections
Radiation source: micro-focus sealed X-ray tube	3697 reflections with I > 2σ(I)
Detector resolution: 10.4498 pixels mm^-1	Rint = 0.109
ω scans	θmax = 36.1°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −10→10
Tmin = 0.889, Tmax = 1.000	k = −12→12
7277 measured reflections	l = −17→17

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.108	H-atom parameters constrained
wR(F^2) = 0.342	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
7277 reflections	Δρmax = 2.21 e Å^−3
110 parameters	Δρmin = −1.81 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

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

	x	y	z	Uiso*/Ueq
Br1	0.41134 (17)	0.8208 (2)	0.09302 (12)	0.0315 (3)
Br2	0.86441 (19)	0.8203 (2)	0.07588 (13)	0.0348 (4)
Br3	0.46903 (19)	0.42010 (19)	0.27237 (14)	0.0341 (4)
Br4	0.91405 (19)	0.41249 (19)	0.23450 (14)	0.0347 (4)
C1	0.7036 (15)	0.9045 (16)	0.3256 (11)	0.022 (2)
C2	0.7288 (17)	1.0710 (17)	0.4348 (13)	0.028 (2)
H2	0.715568	1.185043	0.416531	0.034*
C3	0.7720 (17)	1.0744 (18)	0.5676 (12)	0.029 (3)
H3	0.788550	1.188609	0.640288	0.035*
C4	0.7907 (18)	0.9089 (18)	0.5923 (13)	0.030 (3)
H4	0.822075	0.908007	0.683077	0.036*
C5	0.7643 (18)	0.7436 (16)	0.4865 (11)	0.024 (2)
H5	0.778467	0.630240	0.505706	0.029*
C6	0.7180 (15)	0.7394 (15)	0.3546 (11)	0.020 (2)
C7	0.6622 (17)	0.9234 (18)	0.1888 (12)	0.027 (2)
H7	0.663628	1.059305	0.201844	0.032*
C8	0.6859 (16)	0.5625 (17)	0.2445 (11)	0.026 (2)
H8	0.653309	0.587254	0.156214	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0229 (6)	0.0471 (8)	0.0242 (6)	0.0055 (5)	−0.0001 (4)	0.0120 (5)
Br2	0.0259 (6)	0.0558 (9)	0.0270 (6)	0.0016 (6)	0.0093 (5)	0.0173 (6)
Br3	0.0280 (7)	0.0321 (7)	0.0403 (7)	−0.0065 (5)	0.0070 (5)	0.0085 (6)
Br4	0.0268 (7)	0.0357 (7)	0.0390 (7)	0.0099 (5)	0.0055 (5)	0.0079 (6)
C1	0.017 (5)	0.026 (5)	0.021 (5)	0.000 (4)	0.001 (4)	0.005 (4)
C2	0.023 (6)	0.027 (6)	0.037 (6)	0.002 (4)	0.005 (5)	0.012 (5)
C3	0.028 (6)	0.031 (6)	0.025 (6)	0.004 (5)	0.007 (5)	0.002 (5)
C4	0.028 (6)	0.038 (7)	0.025 (6)	0.003 (5)	0.003 (5)	0.012 (5)
C5	0.031 (6)	0.019 (5)	0.024 (5)	0.000 (4)	0.003 (4)	0.008 (4)
C6	0.014 (5)	0.023 (5)	0.023 (5)	0.003 (4)	0.006 (4)	0.006 (4)
C7	0.029 (6)	0.032 (6)	0.023 (5)	0.010 (5)	0.002 (5)	0.014 (5)
C8	0.016 (5)	0.039 (7)	0.018 (5)	−0.002 (5)	0.003 (4)	0.004 (5)

Geometric parameters (Å, º)

Br1—C7	1.928 (12)	C3—C4	1.369 (18)
Br2—C7	1.957 (12)	C3—H3	0.9500
Br3—C8	1.959 (12)	C4—C5	1.379 (17)
Br4—C8	1.956 (12)	C4—H4	0.9500
C1—C6	1.387 (15)	C5—C6	1.367 (15)
C1—C2	1.403 (16)	C5—H5	0.9500
C1—C7	1.476 (16)	C6—C8	1.461 (15)
C2—C3	1.377 (17)	C7—H7	1.0000
C2—H2	0.9500	C8—H8	1.0000
C6—C1—C2	118.1 (10)	C5—C6—C1	119.6 (10)
C6—C1—C7	126.1 (11)	C5—C6—C8	120.4 (10)
C2—C1—C7	115.8 (11)	C1—C6—C8	120.0 (10)
C3—C2—C1	122.1 (11)	C1—C7—Br1	114.2 (8)
C3—C2—H2	119.0	C1—C7—Br2	111.8 (8)
C1—C2—H2	119.0	Br1—C7—Br2	110.0 (6)
C4—C3—C2	118.3 (11)	C1—C7—H7	106.8
C4—C3—H3	120.9	Br1—C7—H7	106.8
C2—C3—H3	120.9	Br2—C7—H7	106.8
C3—C4—C5	120.6 (11)	C6—C8—Br4	112.1 (8)
C3—C4—H4	119.7	C6—C8—Br3	109.8 (7)
C5—C4—H4	119.7	Br4—C8—Br3	108.2 (6)
C6—C5—C4	121.4 (11)	C6—C8—H8	108.9
C6—C5—H5	119.3	Br4—C8—H8	108.9
C4—C5—H5	119.3	Br3—C8—H8	108.9
C6—C1—C2—C3	1.8 (17)	C7—C1—C6—C8	−1.8 (17)
C7—C1—C2—C3	−178.6 (11)	C6—C1—C7—Br1	63.2 (14)
C1—C2—C3—C4	0.0 (18)	C2—C1—C7—Br1	−116.4 (10)
C2—C3—C4—C5	−0.8 (18)	C6—C1—C7—Br2	−62.5 (14)
C3—C4—C5—C6	−0.3 (19)	C2—C1—C7—Br2	117.9 (10)
C4—C5—C6—C1	2.2 (18)	C5—C6—C8—Br4	−59.7 (12)
C4—C5—C6—C8	−178.4 (11)	C1—C6—C8—Br4	119.6 (10)
C2—C1—C6—C5	−2.8 (16)	C5—C6—C8—Br3	60.6 (12)
C7—C1—C6—C5	177.6 (11)	C1—C6—C8—Br3	−120.0 (10)
C2—C1—C6—C8	177.8 (10)

1-(Bromomethyl)-2-(dibromomethyl)benzene (5)

Crystal data

C8H7Br3	F(000) = 640
Mr = 342.87	Dx = 2.373 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.7746 (3) Å	Cell parameters from 3492 reflections
b = 10.0967 (4) Å	θ = 3.2–29.9°
c = 12.2376 (5) Å	µ = 12.55 mm^−1
β = 92.552 (4)°	T = 250 K
V = 959.67 (7) Å^3	Plate, colourless
Z = 4	0.60 × 0.14 × 0.10 mm

Data collection

SuperNova diffractometer (Agilent Technologies) with Atlas detector	4311 independent reflections
Radiation source: micro-focus sealed X-ray tube	2128 reflections with I > 2σ(I)
Detector resolution: 10.4498 pixels mm^-1	Rint = 0.051
ω scans	θmax = 36.1°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −12→11
Tmin = 0.023, Tmax = 1.000	k = −16→15
13265 measured reflections	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.133	w = 1/[σ^2(Fo^2) + (0.0423P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max < 0.001
4311 reflections	Δρmax = 1.23 e Å^−3
100 parameters	Δρmin = −1.27 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Br1	0.57702 (7)	0.32409 (5)	0.12948 (4)	0.05619 (17)
Br2	0.54674 (7)	0.53573 (5)	0.31575 (5)	0.05977 (17)
Br3	1.09020 (6)	0.43848 (5)	0.38621 (4)	0.04887 (15)
C1	0.8154 (5)	0.5343 (4)	0.1644 (3)	0.0335 (8)
C2	0.7416 (6)	0.6354 (4)	0.1025 (3)	0.0395 (9)
H2	0.621269	0.645685	0.099141	0.047*
C3	0.8416 (6)	0.7208 (5)	0.0458 (4)	0.0448 (10)
H3	0.790066	0.788310	0.002830	0.054*
C4	1.0173 (6)	0.7071 (5)	0.0522 (3)	0.0453 (11)
H4	1.086658	0.767348	0.015518	0.054*
C5	1.0906 (5)	0.6074 (5)	0.1110 (3)	0.0415 (10)
H5	1.210967	0.598064	0.113026	0.050*
C6	0.9934 (5)	0.5182 (4)	0.1684 (3)	0.0334 (8)
C7	0.7055 (5)	0.4440 (4)	0.2254 (3)	0.0356 (9)
H7	0.781996	0.389809	0.274323	0.043*
C8	1.0808 (6)	0.4074 (5)	0.2279 (3)	0.0430 (10)
H8A	1.198021	0.397818	0.202718	0.052*
H8B	1.018626	0.324775	0.211727	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0570 (3)	0.0548 (3)	0.0566 (3)	−0.0201 (2)	−0.0002 (2)	−0.0109 (2)
Br2	0.0669 (3)	0.0501 (3)	0.0650 (3)	−0.0030 (2)	0.0326 (3)	−0.0062 (2)
Br3	0.0432 (3)	0.0659 (4)	0.0373 (2)	0.0049 (2)	−0.00168 (18)	0.00501 (19)
C1	0.0338 (19)	0.039 (2)	0.0278 (17)	−0.0015 (16)	0.0025 (14)	−0.0032 (15)
C2	0.042 (2)	0.042 (2)	0.035 (2)	0.0031 (18)	0.0001 (17)	0.0022 (17)
C3	0.055 (3)	0.038 (2)	0.040 (2)	−0.003 (2)	−0.0054 (19)	0.0030 (18)
C4	0.056 (3)	0.047 (3)	0.033 (2)	−0.016 (2)	0.0071 (19)	−0.0020 (18)
C5	0.034 (2)	0.056 (3)	0.035 (2)	−0.0076 (19)	0.0037 (16)	−0.0004 (19)
C6	0.036 (2)	0.038 (2)	0.0267 (17)	−0.0036 (16)	0.0001 (14)	−0.0066 (15)
C7	0.033 (2)	0.037 (2)	0.036 (2)	0.0002 (16)	−0.0011 (15)	−0.0051 (16)
C8	0.043 (2)	0.047 (3)	0.039 (2)	0.008 (2)	0.0063 (17)	−0.0055 (19)

Geometric parameters (Å, º)

Br1—C7	1.933 (4)	C3—H3	0.9400
Br2—C7	1.930 (4)	C4—C5	1.349 (6)
Br3—C8	1.961 (4)	C4—H4	0.9400
C1—C2	1.381 (6)	C5—C6	1.387 (6)
C1—C6	1.392 (5)	C5—H5	0.9400
C1—C7	1.475 (6)	C6—C8	1.483 (6)
C2—C3	1.370 (6)	C7—H7	0.9900
C2—H2	0.9400	C8—H8A	0.9800
C3—C4	1.372 (6)	C8—H8B	0.9800
C2—C1—C6	119.6 (4)	C5—C6—C1	118.0 (4)
C2—C1—C7	119.9 (4)	C5—C6—C8	119.4 (4)
C6—C1—C7	120.5 (4)	C1—C6—C8	122.6 (4)
C3—C2—C1	120.8 (4)	C1—C7—Br2	113.1 (3)
C3—C2—H2	119.6	C1—C7—Br1	112.0 (3)
C1—C2—H2	119.6	Br2—C7—Br1	108.80 (19)
C2—C3—C4	119.6 (4)	C1—C7—H7	107.5
C2—C3—H3	120.2	Br2—C7—H7	107.5
C4—C3—H3	120.2	Br1—C7—H7	107.5
C5—C4—C3	120.1 (4)	C6—C8—Br3	111.1 (3)
C5—C4—H4	120.0	C6—C8—H8A	109.4
C3—C4—H4	120.0	Br3—C8—H8A	109.4
C4—C5—C6	121.9 (4)	C6—C8—H8B	109.4
C4—C5—H5	119.1	Br3—C8—H8B	109.4
C6—C5—H5	119.1	H8A—C8—H8B	108.0
C6—C1—C2—C3	−0.7 (6)	C2—C1—C6—C8	−176.3 (4)
C7—C1—C2—C3	179.6 (4)	C7—C1—C6—C8	3.4 (6)
C1—C2—C3—C4	−1.1 (7)	C2—C1—C7—Br2	−51.5 (4)
C2—C3—C4—C5	2.2 (7)	C6—C1—C7—Br2	128.8 (3)
C3—C4—C5—C6	−1.6 (7)	C2—C1—C7—Br1	72.0 (4)
C4—C5—C6—C1	−0.2 (6)	C6—C1—C7—Br1	−107.8 (4)
C4—C5—C6—C8	177.5 (4)	C5—C6—C8—Br3	105.9 (4)
C2—C1—C6—C5	1.3 (6)	C1—C6—C8—Br3	−76.4 (4)
C7—C1—C6—C5	−179.0 (4)

2-(Bromomethyl)-3-(dibromomethyl)naphthalene (6)

Crystal data

C12H9Br3	F(000) = 744
Mr = 392.92	Dx = 2.203 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 4.8140 (2) Å	Cell parameters from 5091 reflections
b = 10.1694 (3) Å	θ = 3.9–32.5°
c = 24.2052 (9) Å	µ = 10.18 mm^−1
β = 90.711 (3)°	T = 200 K
V = 1184.89 (7) Å^3	Plate, colourless
Z = 4	0.21 × 0.04 × 0.04 mm

Data collection

SuperNova diffractometer (Agilent Technologies) with Atlas detector	5379 independent reflections
Radiation source: micro-focus sealed X-ray tube	3335 reflections with I > 2σ(I)
Detector resolution: 10.4498 pixels mm^-1	Rint = 0.044
ω scans	θmax = 36.2°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −7→7
Tmin = 0.472, Tmax = 1.000	k = −16→13
17302 measured reflections	l = −39→39

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0338P)^2 + 1.9947P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
5379 reflections	Δρmax = 0.93 e Å^−3
136 parameters	Δρmin = −0.99 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Br1	0.78256 (9)	0.80688 (4)	0.17241 (2)	0.03945 (11)
Br2	1.14468 (9)	0.83875 (4)	0.06533 (2)	0.04077 (11)
Br3	1.14003 (9)	1.05749 (4)	0.27073 (2)	0.03982 (11)
C1	0.7412 (7)	1.0819 (3)	0.09060 (14)	0.0258 (6)
H1	0.668957	1.012418	0.068480	0.031*
C2	0.9457 (7)	1.0550 (3)	0.12852 (14)	0.0255 (6)
C3	1.0536 (7)	1.1578 (4)	0.16220 (14)	0.0275 (7)
C4	0.9491 (8)	1.2813 (4)	0.15526 (15)	0.0309 (7)
H4	1.021166	1.350291	0.177664	0.037*
C4A	0.7407 (8)	1.3106 (3)	0.11667 (15)	0.0292 (7)
C5	0.6353 (10)	1.4392 (4)	0.10847 (18)	0.0397 (9)
H5	0.708868	1.509973	0.129652	0.048*
C6	0.4323 (10)	1.4623 (4)	0.07110 (19)	0.0462 (11)
H6	0.362221	1.548979	0.066556	0.055*
C7	0.3233 (9)	1.3601 (4)	0.03885 (18)	0.0414 (10)
H7	0.178785	1.377828	0.012816	0.050*
C8	0.4218 (8)	1.2366 (4)	0.04443 (16)	0.0344 (8)
H8	0.347647	1.167912	0.022095	0.041*
C8A	0.6348 (7)	1.2091 (3)	0.08336 (14)	0.0267 (7)
C9	1.0491 (7)	0.9181 (4)	0.13535 (16)	0.0303 (7)
H9	1.221456	0.921329	0.158800	0.036*
C10	1.2808 (8)	1.1373 (4)	0.20320 (15)	0.0345 (8)
H10A	1.368647	1.222802	0.212177	0.041*
H10B	1.424278	1.079483	0.187139	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0374 (2)	0.03034 (19)	0.0506 (3)	0.00059 (15)	0.00073 (17)	0.01124 (16)
Br2	0.0430 (2)	0.0360 (2)	0.0433 (2)	0.00720 (17)	0.00150 (17)	−0.01260 (17)
Br3	0.0461 (2)	0.0454 (2)	0.02807 (18)	0.00442 (18)	0.00168 (15)	0.00543 (16)
C1	0.0275 (16)	0.0251 (15)	0.0250 (15)	−0.0008 (12)	0.0010 (12)	−0.0040 (12)
C2	0.0268 (16)	0.0243 (15)	0.0257 (15)	−0.0009 (12)	0.0029 (12)	−0.0014 (12)
C3	0.0279 (16)	0.0324 (17)	0.0223 (15)	−0.0054 (13)	0.0050 (12)	−0.0026 (13)
C4	0.040 (2)	0.0273 (17)	0.0256 (16)	−0.0080 (14)	0.0079 (14)	−0.0049 (13)
C4A	0.0361 (18)	0.0248 (16)	0.0270 (16)	−0.0002 (14)	0.0096 (14)	0.0007 (13)
C5	0.056 (3)	0.0255 (18)	0.038 (2)	0.0042 (17)	0.0169 (18)	0.0008 (15)
C6	0.059 (3)	0.035 (2)	0.044 (2)	0.018 (2)	0.018 (2)	0.0132 (18)
C7	0.043 (2)	0.047 (2)	0.035 (2)	0.0139 (19)	0.0063 (17)	0.0121 (18)
C8	0.0360 (19)	0.039 (2)	0.0278 (18)	0.0046 (16)	0.0054 (14)	0.0045 (15)
C8A	0.0282 (16)	0.0275 (16)	0.0247 (15)	0.0026 (13)	0.0071 (12)	0.0034 (12)
C9	0.0264 (16)	0.0302 (17)	0.0341 (18)	0.0003 (13)	−0.0011 (14)	−0.0034 (14)
C10	0.0324 (18)	0.046 (2)	0.0255 (17)	−0.0059 (16)	0.0040 (14)	−0.0051 (15)

Geometric parameters (Å, º)

Br1—C9	1.939 (4)	C4A—C5	1.415 (5)
Br2—C9	1.938 (4)	C5—C6	1.344 (7)
Br3—C10	1.954 (4)	C5—H5	0.9500
C1—C2	1.366 (5)	C6—C7	1.398 (7)
C1—C8A	1.401 (5)	C6—H6	0.9500
C1—H1	0.9500	C7—C8	1.349 (6)
C2—C3	1.420 (5)	C7—H7	0.9500
C2—C9	1.487 (5)	C8—C8A	1.412 (5)
C3—C4	1.363 (5)	C8—H8	0.9500
C3—C10	1.483 (5)	C9—H9	1.0000
C4—C4A	1.395 (5)	C10—H10A	0.9900
C4—H4	0.9500	C10—H10B	0.9900
C4A—C8A	1.402 (5)
C2—C1—C8A	121.9 (3)	C8—C7—C6	120.5 (4)
C2—C1—H1	119.0	C8—C7—H7	119.8
C8A—C1—H1	119.0	C6—C7—H7	119.8
C1—C2—C3	119.6 (3)	C7—C8—C8A	120.2 (4)
C1—C2—C9	120.0 (3)	C7—C8—H8	119.9
C3—C2—C9	120.4 (3)	C8A—C8—H8	119.9
C4—C3—C2	118.4 (3)	C1—C8A—C4A	118.6 (3)
C4—C3—C10	118.7 (3)	C1—C8A—C8	121.8 (3)
C2—C3—C10	122.8 (3)	C4A—C8A—C8	119.6 (3)
C3—C4—C4A	122.8 (3)	C2—C9—Br2	112.0 (3)
C3—C4—H4	118.6	C2—C9—Br1	112.0 (2)
C4A—C4—H4	118.6	Br2—C9—Br1	109.13 (18)
C4—C4A—C8A	118.8 (3)	C2—C9—H9	107.8
C4—C4A—C5	123.0 (4)	Br2—C9—H9	107.8
C8A—C4A—C5	118.2 (4)	Br1—C9—H9	107.8
C6—C5—C4A	120.8 (4)	C3—C10—Br3	111.0 (2)
C6—C5—H5	119.6	C3—C10—H10A	109.4
C4A—C5—H5	119.6	Br3—C10—H10A	109.4
C5—C6—C7	120.7 (4)	C3—C10—H10B	109.4
C5—C6—H6	119.6	Br3—C10—H10B	109.4
C7—C6—H6	119.6	H10A—C10—H10B	108.0
C8A—C1—C2—C3	0.6 (5)	C2—C1—C8A—C4A	−0.7 (5)
C8A—C1—C2—C9	179.0 (3)	C2—C1—C8A—C8	−179.5 (3)
C1—C2—C3—C4	−0.3 (5)	C4—C4A—C8A—C1	0.6 (5)
C9—C2—C3—C4	−178.7 (3)	C5—C4A—C8A—C1	179.0 (3)
C1—C2—C3—C10	−178.3 (3)	C4—C4A—C8A—C8	179.4 (3)
C9—C2—C3—C10	3.3 (5)	C5—C4A—C8A—C8	−2.2 (5)
C2—C3—C4—C4A	0.2 (5)	C7—C8—C8A—C1	179.6 (4)
C10—C3—C4—C4A	178.2 (3)	C7—C8—C8A—C4A	0.8 (5)
C3—C4—C4A—C8A	−0.3 (5)	C1—C2—C9—Br2	50.1 (4)
C3—C4—C4A—C5	−178.7 (4)	C3—C2—C9—Br2	−131.5 (3)
C4—C4A—C5—C6	−179.4 (4)	C1—C2—C9—Br1	−72.9 (4)
C8A—C4A—C5—C6	2.3 (6)	C3—C2—C9—Br1	105.5 (3)
C4A—C5—C6—C7	−0.9 (6)	C4—C3—C10—Br3	102.9 (3)
C5—C6—C7—C8	−0.5 (6)	C2—C3—C10—Br3	−79.2 (4)
C6—C7—C8—C8A	0.6 (6)

2,3-Bis(dibromomethyl)naphthalene (7)

Crystal data

C12H8Br4	F(000) = 880
Mr = 471.82	Dx = 2.338 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.5581 (2) Å	Cell parameters from 5724 reflections
b = 12.4074 (3) Å	θ = 3.3–34.7°
c = 10.2943 (2) Å	µ = 11.98 mm^−1
β = 96.363 (2)°	T = 298 K
V = 1340.23 (5) Å^3	Polyhedron, colourless
Z = 4	0.38 × 0.29 × 0.24 mm

Data collection

Xcalibur diffractometer (Oxford Diffraction) with Sapphire3 detector	5310 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3179 reflections with I > 2σ(I)
Detector resolution: 16.0328 pixels mm^-1	Rint = 0.057
ω scans	θmax = 34.8°, θmin = 3.3°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −16→16
Tmin = 0.432, Tmax = 1.000	k = −19→16
31095 measured reflections	l = −15→13

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0205P)^2 + 3.2815P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.001
5310 reflections	Δρmax = 0.70 e Å^−3
145 parameters	Δρmin = −1.03 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Br1	0.15396 (5)	0.13904 (4)	0.62716 (5)	0.05199 (14)
Br2	0.23360 (5)	−0.04114 (5)	0.43146 (5)	0.05596 (16)
Br3	0.00797 (5)	−0.07618 (5)	0.84843 (5)	0.05205 (15)
Br4	0.08087 (5)	−0.26658 (4)	0.66327 (6)	0.05615 (16)
C1	0.4601 (4)	−0.0221 (4)	0.7514 (4)	0.0358 (9)
H1	0.511481	0.025823	0.711631	0.043*
C2	0.3338 (4)	−0.0301 (3)	0.7033 (4)	0.0307 (8)
C3	0.2548 (4)	−0.1036 (3)	0.7639 (4)	0.0295 (8)
C4	0.3063 (4)	−0.1626 (3)	0.8680 (4)	0.0360 (9)
H4	0.253922	−0.209708	0.907708	0.043*
C4A	0.4358 (4)	−0.1555 (3)	0.9180 (4)	0.0357 (9)
C5	0.4887 (5)	−0.2176 (4)	1.0268 (5)	0.0451 (11)
H5	0.437568	−0.265289	1.067344	0.054*
C6	0.6142 (5)	−0.2072 (4)	1.0714 (5)	0.0517 (13)
H6	0.648611	−0.248607	1.142016	0.062*
C7	0.6925 (5)	−0.1352 (5)	1.0126 (5)	0.0518 (13)
H7	0.777937	−0.128800	1.044943	0.062*
C8	0.6446 (4)	−0.0745 (4)	0.9086 (5)	0.0466 (11)
H8	0.697670	−0.026927	0.870492	0.056*
C8A	0.5150 (4)	−0.0830 (4)	0.8580 (4)	0.0342 (9)
C9	0.2897 (4)	0.0410 (4)	0.5905 (4)	0.0387 (10)
H9	0.362488	0.085202	0.572005	0.046*
C10	0.1168 (4)	−0.1177 (3)	0.7156 (4)	0.0329 (9)
H10	0.096513	−0.071300	0.639084	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0446 (3)	0.0430 (3)	0.0683 (3)	0.0108 (2)	0.0061 (2)	0.0094 (2)
Br2	0.0595 (3)	0.0758 (4)	0.0332 (2)	0.0016 (3)	0.0079 (2)	0.0041 (2)
Br3	0.0356 (2)	0.0746 (4)	0.0480 (3)	0.0080 (2)	0.0141 (2)	0.0100 (2)
Br4	0.0514 (3)	0.0511 (3)	0.0632 (3)	−0.0172 (2)	−0.0061 (2)	−0.0070 (2)
C1	0.026 (2)	0.040 (2)	0.042 (2)	−0.0031 (18)	0.0116 (17)	−0.0013 (19)
C2	0.0259 (19)	0.031 (2)	0.036 (2)	0.0010 (16)	0.0088 (16)	0.0017 (17)
C3	0.0267 (19)	0.030 (2)	0.0321 (19)	−0.0024 (16)	0.0052 (16)	−0.0020 (16)
C4	0.033 (2)	0.034 (2)	0.040 (2)	−0.0085 (18)	0.0011 (18)	0.0028 (18)
C4A	0.036 (2)	0.031 (2)	0.039 (2)	0.0015 (18)	−0.0017 (18)	−0.0040 (17)
C5	0.043 (3)	0.041 (3)	0.048 (3)	0.000 (2)	−0.007 (2)	0.005 (2)
C6	0.050 (3)	0.050 (3)	0.051 (3)	0.013 (2)	−0.014 (2)	−0.004 (2)
C7	0.031 (2)	0.065 (3)	0.057 (3)	0.006 (2)	−0.007 (2)	−0.013 (3)
C8	0.031 (2)	0.057 (3)	0.053 (3)	0.003 (2)	0.008 (2)	−0.009 (2)
C8A	0.0258 (19)	0.041 (2)	0.036 (2)	0.0018 (18)	0.0045 (16)	−0.0073 (18)
C9	0.031 (2)	0.044 (3)	0.042 (2)	−0.0008 (19)	0.0081 (18)	0.0094 (19)
C10	0.028 (2)	0.040 (2)	0.031 (2)	−0.0021 (17)	0.0037 (16)	0.0027 (17)

Geometric parameters (Å, º)

Br1—C9	1.948 (4)	C4A—C8A	1.415 (6)
Br2—C9	1.964 (5)	C4A—C5	1.422 (6)
Br3—C10	1.950 (4)	C5—C6	1.360 (7)
Br4—C10	1.950 (4)	C5—H5	0.9300
C1—C2	1.374 (6)	C6—C7	1.399 (8)
C1—C8A	1.403 (6)	C6—H6	0.9300
C1—H1	0.9300	C7—C8	1.360 (7)
C2—C3	1.425 (5)	C7—H7	0.9300
C2—C9	1.492 (6)	C8—C8A	1.413 (6)
C3—C4	1.361 (6)	C8—H8	0.9300
C3—C10	1.497 (6)	C9—H9	0.9800
C4—C4A	1.409 (6)	C10—H10	0.9800
C4—H4	0.9300
C2—C1—C8A	122.9 (4)	C8—C7—C6	120.6 (4)
C2—C1—H1	118.6	C8—C7—H7	119.7
C8A—C1—H1	118.6	C6—C7—H7	119.7
C1—C2—C3	118.7 (4)	C7—C8—C8A	120.6 (5)
C1—C2—C9	116.4 (4)	C7—C8—H8	119.7
C3—C2—C9	124.9 (4)	C8A—C8—H8	119.7
C4—C3—C2	119.1 (4)	C1—C8A—C8	123.2 (4)
C4—C3—C10	119.2 (4)	C1—C8A—C4A	118.1 (4)
C2—C3—C10	121.7 (4)	C8—C8A—C4A	118.8 (4)
C3—C4—C4A	122.7 (4)	C2—C9—Br1	113.1 (3)
C3—C4—H4	118.6	C2—C9—Br2	112.4 (3)
C4A—C4—H4	118.6	Br1—C9—Br2	109.0 (2)
C4—C4A—C8A	118.5 (4)	C2—C9—H9	107.4
C4—C4A—C5	122.3 (4)	Br1—C9—H9	107.4
C8A—C4A—C5	119.3 (4)	Br2—C9—H9	107.4
C6—C5—C4A	119.8 (5)	C3—C10—Br3	111.3 (3)
C6—C5—H5	120.1	C3—C10—Br4	110.8 (3)
C4A—C5—H5	120.1	Br3—C10—Br4	109.42 (19)
C5—C6—C7	121.0 (5)	C3—C10—H10	108.4
C5—C6—H6	119.5	Br3—C10—H10	108.4
C7—C6—H6	119.5	Br4—C10—H10	108.4
C8A—C1—C2—C3	−0.1 (6)	C2—C1—C8A—C4A	−0.2 (6)
C8A—C1—C2—C9	179.3 (4)	C7—C8—C8A—C1	179.6 (4)
C1—C2—C3—C4	0.6 (6)	C7—C8—C8A—C4A	0.4 (7)
C9—C2—C3—C4	−178.8 (4)	C4—C4A—C8A—C1	−0.1 (6)
C1—C2—C3—C10	−179.2 (4)	C5—C4A—C8A—C1	−179.5 (4)
C9—C2—C3—C10	1.5 (6)	C4—C4A—C8A—C8	179.3 (4)
C2—C3—C4—C4A	−0.8 (6)	C5—C4A—C8A—C8	−0.2 (6)
C10—C3—C4—C4A	178.9 (4)	C1—C2—C9—Br1	−120.3 (4)
C3—C4—C4A—C8A	0.6 (6)	C3—C2—C9—Br1	59.0 (5)
C3—C4—C4A—C5	−180.0 (4)	C1—C2—C9—Br2	115.7 (4)
C4—C4A—C5—C6	−179.8 (5)	C3—C2—C9—Br2	−64.9 (5)
C8A—C4A—C5—C6	−0.3 (7)	C4—C3—C10—Br3	62.8 (5)
C4A—C5—C6—C7	0.7 (8)	C2—C3—C10—Br3	−117.5 (4)
C5—C6—C7—C8	−0.5 (8)	C4—C3—C10—Br4	−59.2 (4)
C6—C7—C8—C8A	0.0 (8)	C2—C3—C10—Br4	120.5 (4)
C2—C1—C8A—C8	−179.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Br1	0.98	2.69	3.348 (4)	125
C10—H10···Br2	0.98	2.74	3.432 (4)	128

1-(Bromomethyl)-2-(dibromomethyl)naphthalene (8)

Crystal data

C12H9Br3	Z = 2
Mr = 392.92	F(000) = 372
Triclinic, P1	Dx = 2.182 Mg m^−3
a = 7.2881 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4508 (4) Å	Cell parameters from 3204 reflections
c = 9.9371 (4) Å	θ = 3.6–36.0°
α = 78.382 (4)°	µ = 10.08 mm^−1
β = 87.102 (3)°	T = 100 K
γ = 86.663 (4)°	Polyhedron, colourless
V = 598.00 (5) Å^3	0.60 × 0.31 × 0.09 mm

Data collection

SuperNova diffractometer (Agilent Technologies) with Atlas detector	5194 independent reflections
Radiation source: micro-focus sealed X-ray tube	2876 reflections with I > 2σ(I)
Detector resolution: 10.4498 pixels mm^-1	Rint = 0.060
ω scans	θmax = 36.2°, θmin = 3.4°
Absorption correction: multi-scan CrysAlis PRO (Rigaku OD, 2015)	h = −12→11
Tmin = 0.074, Tmax = 1.000	k = −13→13
8918 measured reflections	l = −15→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.075	H-atom parameters constrained
wR(F^2) = 0.207	w = 1/[σ^2(Fo^2) + (0.0715P)^2 + 1.8986P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
5194 reflections	Δρmax = 1.34 e Å^−3
136 parameters	Δρmin = −1.24 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Br1	0.28015 (8)	0.92558 (9)	0.45289 (6)	0.03841 (18)
Br2	0.40506 (10)	0.39139 (10)	0.37129 (8)	0.0510 (2)
Br3	−0.02179 (10)	0.42173 (9)	0.31504 (8)	0.0465 (2)
C1	0.1841 (7)	0.8316 (7)	0.2022 (6)	0.0265 (10)
C2	0.2250 (7)	0.6707 (7)	0.2028 (6)	0.0303 (11)
C3	0.2955 (8)	0.6199 (8)	0.0818 (7)	0.0358 (12)
H3	0.321402	0.508018	0.083500	0.043*
C4	0.3263 (8)	0.7295 (8)	−0.0364 (6)	0.0337 (12)
H4	0.371440	0.693502	−0.117039	0.040*
C4A	0.2915 (7)	0.8969 (8)	−0.0403 (6)	0.0304 (11)
C5	0.3296 (8)	1.0124 (9)	−0.1630 (6)	0.0373 (14)
H5	0.378980	0.977219	−0.242921	0.045*
C6	0.2950 (9)	1.1739 (9)	−0.1655 (7)	0.0425 (16)
H6	0.320198	1.250640	−0.247321	0.051*
C7	0.2230 (8)	1.2260 (8)	−0.0486 (7)	0.0409 (15)
H7	0.197932	1.338331	−0.052434	0.049*
C8	0.1873 (8)	1.1187 (8)	0.0721 (7)	0.0348 (12)
H8	0.140219	1.157621	0.150924	0.042*
C8A	0.2203 (7)	0.9497 (7)	0.0798 (6)	0.0293 (11)
C9	0.0956 (7)	0.8842 (7)	0.3263 (6)	0.0297 (11)
H9A	0.014943	0.799131	0.375563	0.036*
H9B	0.017821	0.983958	0.296693	0.036*
C10	0.1955 (8)	0.5447 (8)	0.3301 (7)	0.0362 (13)
H10	0.172094	0.600708	0.409304	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0383 (3)	0.0474 (4)	0.0316 (3)	−0.0061 (2)	−0.0033 (2)	−0.0113 (3)
Br2	0.0538 (4)	0.0470 (4)	0.0492 (4)	0.0106 (3)	−0.0103 (3)	−0.0045 (3)
Br3	0.0458 (4)	0.0437 (4)	0.0475 (4)	−0.0114 (3)	0.0069 (3)	−0.0023 (3)
C1	0.021 (2)	0.031 (3)	0.030 (3)	−0.0013 (18)	−0.0011 (18)	−0.012 (2)
C2	0.028 (2)	0.032 (3)	0.030 (3)	0.000 (2)	0.004 (2)	−0.007 (2)
C3	0.037 (3)	0.036 (3)	0.038 (3)	0.002 (2)	−0.002 (2)	−0.016 (2)
C4	0.033 (3)	0.039 (3)	0.032 (3)	−0.003 (2)	0.001 (2)	−0.013 (2)
C4A	0.020 (2)	0.045 (3)	0.025 (2)	−0.005 (2)	0.0019 (18)	−0.003 (2)
C5	0.029 (3)	0.055 (4)	0.027 (3)	−0.007 (2)	−0.001 (2)	−0.004 (3)
C6	0.036 (3)	0.048 (4)	0.039 (3)	−0.008 (3)	−0.011 (3)	0.007 (3)
C7	0.036 (3)	0.033 (3)	0.052 (4)	−0.004 (2)	−0.014 (3)	0.000 (3)
C8	0.029 (2)	0.039 (3)	0.038 (3)	−0.002 (2)	−0.005 (2)	−0.010 (2)
C8A	0.020 (2)	0.037 (3)	0.031 (3)	−0.0003 (19)	−0.0053 (18)	−0.005 (2)
C9	0.024 (2)	0.038 (3)	0.030 (3)	0.0033 (19)	−0.0025 (19)	−0.014 (2)
C10	0.041 (3)	0.032 (3)	0.036 (3)	0.003 (2)	0.000 (2)	−0.008 (2)

Geometric parameters (Å, º)

Br1—C9	1.979 (5)	C4A—C5	1.426 (8)
Br2—C10	1.949 (6)	C5—C6	1.369 (11)
Br3—C10	1.972 (7)	C5—H5	0.9500
C1—C2	1.374 (8)	C6—C7	1.391 (11)
C1—C8A	1.433 (8)	C6—H6	0.9500
C1—C9	1.497 (8)	C7—C8	1.374 (9)
C2—C3	1.419 (8)	C7—H7	0.9500
C2—C10	1.496 (8)	C8—C8A	1.422 (9)
C3—C4	1.360 (9)	C8—H8	0.9500
C3—H3	0.9500	C9—H9A	0.9900
C4—C4A	1.416 (9)	C9—H9B	0.9900
C4—H4	0.9500	C10—H10	1.0000
C4A—C8A	1.420 (8)
C2—C1—C8A	119.6 (5)	C8—C7—C6	121.5 (7)
C2—C1—C9	120.7 (5)	C8—C7—H7	119.2
C8A—C1—C9	119.7 (5)	C6—C7—H7	119.2
C1—C2—C3	120.6 (5)	C7—C8—C8A	120.3 (6)
C1—C2—C10	121.1 (5)	C7—C8—H8	119.8
C3—C2—C10	118.3 (5)	C8A—C8—H8	119.8
C4—C3—C2	120.7 (6)	C4A—C8A—C8	117.9 (5)
C4—C3—H3	119.7	C4A—C8A—C1	119.1 (5)
C2—C3—H3	119.7	C8—C8A—C1	123.0 (6)
C3—C4—C4A	120.5 (6)	C1—C9—Br1	111.9 (3)
C3—C4—H4	119.8	C1—C9—H9A	109.2
C4A—C4—H4	119.8	Br1—C9—H9A	109.2
C4—C4A—C8A	119.5 (5)	C1—C9—H9B	109.2
C4—C4A—C5	120.5 (6)	Br1—C9—H9B	109.2
C8A—C4A—C5	120.0 (6)	H9A—C9—H9B	107.9
C6—C5—C4A	120.0 (6)	C2—C10—Br2	113.6 (4)
C6—C5—H5	120.0	C2—C10—Br3	110.6 (4)
C4A—C5—H5	120.0	Br2—C10—Br3	108.2 (3)
C5—C6—C7	120.2 (6)	C2—C10—H10	108.1
C5—C6—H6	119.9	Br2—C10—H10	108.1
C7—C6—H6	119.9	Br3—C10—H10	108.1
C8A—C1—C2—C3	−2.7 (8)	C5—C4A—C8A—C8	0.7 (7)
C9—C1—C2—C3	175.0 (5)	C4—C4A—C8A—C1	−0.4 (7)
C8A—C1—C2—C10	177.7 (5)	C5—C4A—C8A—C1	−179.6 (5)
C9—C1—C2—C10	−4.6 (8)	C7—C8—C8A—C4A	0.3 (8)
C1—C2—C3—C4	0.9 (9)	C7—C8—C8A—C1	−179.3 (5)
C10—C2—C3—C4	−179.5 (5)	C2—C1—C8A—C4A	2.4 (7)
C2—C3—C4—C4A	1.1 (9)	C9—C1—C8A—C4A	−175.3 (5)
C3—C4—C4A—C8A	−1.3 (8)	C2—C1—C8A—C8	−178.0 (5)
C3—C4—C4A—C5	177.9 (5)	C9—C1—C8A—C8	4.3 (7)
C4—C4A—C5—C6	179.8 (5)	C2—C1—C9—Br1	89.4 (6)
C8A—C4A—C5—C6	−0.9 (8)	C8A—C1—C9—Br1	−93.0 (5)
C4A—C5—C6—C7	0.1 (9)	C1—C2—C10—Br2	−132.4 (5)
C5—C6—C7—C8	1.0 (9)	C3—C2—C10—Br2	48.0 (7)
C6—C7—C8—C8A	−1.2 (9)	C1—C2—C10—Br3	105.8 (6)
C4—C4A—C8A—C8	179.9 (5)	C3—C2—C10—Br3	−73.8 (6)

1,3-Bis(dibromomethyl)benzene (9)

Crystal data

C8H6Br4	F(000) = 776
Mr = 421.77	Dx = 2.609 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.0060 (3) Å	Cell parameters from 7961 reflections
b = 6.09685 (11) Å	θ = 3.3–35.8°
c = 14.7104 (3) Å	µ = 14.94 mm^−1
β = 94.201 (2)°	T = 100 K
V = 1073.90 (4) Å^3	Parallelepiped, colorless
Z = 4	0.30 × 0.15 × 0.07 mm

Data collection

SuperNova diffractometer (Agilent Technologies) with Atlas detector	4762 independent reflections
Radiation source: micro-focus sealed X-ray tube	3800 reflections with I > 2σ(I)
Detector resolution: 10.4498 pixels mm^-1	Rint = 0.035
ω scans	θmax = 35.9°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −13→19
Tmin = 0.181, Tmax = 1.000	k = −9→9
14593 measured reflections	l = −23→24

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0422P)^2 + 2.5893P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
4762 reflections	Δρmax = 1.86 e Å^−3
109 parameters	Δρmin = −1.74 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Br1	0.32963 (3)	1.11032 (5)	0.45526 (2)	0.01661 (8)
Br2	0.43121 (3)	1.55571 (5)	0.38181 (2)	0.01892 (8)
Br3	0.61848 (3)	0.48600 (6)	0.13012 (3)	0.02499 (9)
Br4	0.75290 (3)	0.92849 (6)	0.10397 (2)	0.01652 (7)
C1	0.5458 (3)	1.0063 (5)	0.2812 (2)	0.0130 (5)
H1	0.603349	0.984055	0.328189	0.016*
C2	0.4544 (3)	1.1378 (5)	0.2971 (2)	0.0129 (5)
C3	0.3701 (3)	1.1716 (6)	0.2278 (2)	0.0193 (6)
H3	0.307946	1.262182	0.238334	0.023*
C4	0.3775 (3)	1.0724 (7)	0.1436 (2)	0.0216 (7)
H4	0.320037	1.094662	0.096579	0.026*
C5	0.4683 (3)	0.9411 (6)	0.1277 (2)	0.0184 (6)
H5	0.472850	0.873793	0.069858	0.022*
C6	0.5530 (3)	0.9073 (5)	0.1965 (2)	0.0133 (5)
C7	0.4495 (3)	1.2396 (5)	0.3894 (2)	0.0141 (5)
H7	0.521897	1.208715	0.425019	0.017*
C8	0.6545 (3)	0.7717 (5)	0.1822 (2)	0.0160 (6)
H8	0.696048	0.748803	0.242854	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01907 (16)	0.01562 (14)	0.01619 (14)	−0.00083 (11)	0.00843 (11)	0.00105 (11)
Br2	0.02052 (16)	0.01306 (14)	0.02327 (16)	−0.00087 (11)	0.00210 (12)	−0.00014 (11)
Br3	0.0332 (2)	0.01435 (15)	0.02843 (18)	−0.00225 (13)	0.00873 (15)	−0.00420 (13)
Br4	0.01571 (15)	0.01850 (15)	0.01610 (13)	−0.00009 (11)	0.00622 (11)	−0.00005 (11)
C1	0.0170 (14)	0.0108 (12)	0.0114 (11)	−0.0014 (10)	0.0028 (10)	−0.0002 (9)
C2	0.0134 (13)	0.0137 (12)	0.0122 (11)	−0.0011 (10)	0.0049 (10)	0.0003 (10)
C3	0.0142 (14)	0.0277 (17)	0.0159 (13)	0.0034 (12)	0.0016 (11)	−0.0032 (12)
C4	0.0162 (15)	0.0326 (19)	0.0157 (13)	0.0009 (13)	−0.0015 (11)	−0.0050 (13)
C5	0.0188 (15)	0.0240 (16)	0.0127 (12)	0.0000 (12)	0.0025 (11)	−0.0040 (11)
C6	0.0155 (14)	0.0112 (12)	0.0138 (12)	0.0000 (10)	0.0046 (10)	−0.0003 (10)
C7	0.0141 (13)	0.0143 (12)	0.0144 (12)	−0.0016 (10)	0.0041 (10)	−0.0001 (10)
C8	0.0193 (15)	0.0157 (13)	0.0136 (12)	0.0010 (11)	0.0059 (11)	−0.0005 (10)

Geometric parameters (Å, º)

Br1—C7	1.958 (3)	C3—C4	1.387 (5)
Br2—C7	1.942 (3)	C3—H3	0.9500
Br3—C8	1.939 (3)	C4—C5	1.386 (5)
Br4—C8	1.958 (3)	C4—H4	0.9500
C1—C2	1.393 (4)	C5—C6	1.396 (5)
C1—C6	1.393 (4)	C5—H5	0.9500
C1—H1	0.9500	C6—C8	1.500 (5)
C2—C3	1.399 (4)	C7—H7	1.0000
C2—C7	1.498 (4)	C8—H8	1.0000
C2—C1—C6	120.0 (3)	C1—C6—C5	119.7 (3)
C2—C1—H1	120.0	C1—C6—C8	117.9 (3)
C6—C1—H1	120.0	C5—C6—C8	122.4 (3)
C1—C2—C3	120.0 (3)	C2—C7—Br2	111.8 (2)
C1—C2—C7	118.3 (3)	C2—C7—Br1	111.2 (2)
C3—C2—C7	121.7 (3)	Br2—C7—Br1	110.10 (15)
C4—C3—C2	119.8 (3)	C2—C7—H7	107.9
C4—C3—H3	120.1	Br2—C7—H7	107.9
C2—C3—H3	120.1	Br1—C7—H7	107.9
C5—C4—C3	120.3 (3)	C6—C8—Br3	113.0 (2)
C5—C4—H4	119.8	C6—C8—Br4	110.2 (2)
C3—C4—H4	119.8	Br3—C8—Br4	109.46 (15)
C4—C5—C6	120.2 (3)	C6—C8—H8	108.0
C4—C5—H5	119.9	Br3—C8—H8	108.0
C6—C5—H5	119.9	Br4—C8—H8	108.0
C6—C1—C2—C3	−0.4 (5)	C4—C5—C6—C8	−178.3 (3)
C6—C1—C2—C7	179.5 (3)	C1—C2—C7—Br2	125.3 (3)
C1—C2—C3—C4	0.5 (5)	C3—C2—C7—Br2	−54.8 (4)
C7—C2—C3—C4	−179.4 (3)	C1—C2—C7—Br1	−111.2 (3)
C2—C3—C4—C5	−0.3 (6)	C3—C2—C7—Br1	68.7 (4)
C3—C4—C5—C6	0.1 (6)	C1—C6—C8—Br3	130.9 (3)
C2—C1—C6—C5	0.1 (5)	C5—C6—C8—Br3	−50.7 (4)
C2—C1—C6—C8	178.6 (3)	C1—C6—C8—Br4	−106.3 (3)
C4—C5—C6—C1	0.0 (5)	C5—C6—C8—Br4	72.1 (4)