The 1:1 co-crystal of 2-bromo­naphthalene-1,4-dione and 1,8-di­hydroxy­anthracene-9,10-dione: crystal structure and Hirshfeld surface analysis

The 1:1 co-crystal comprising two fused-ring mol­ecules features significant hydrogen bonding between the 1,8-di­hydroxy­anthra­quinone coformers with the main links between the resulting dimeric aggregates and the bromo­naphtho­quinone coformer being of the type C—H...O.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.025
• wR factor = 0.075
• Data-to-parameter ratio = 12.3

checkCIF/PLATON results

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Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         16 Report
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00003 Ang.
PLAT143_ALERT_4_G s.u. on c - Axis Small or Missing ..............    0.00016 Ang.
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C19    -C23           1.45 Ang.
PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C1     -C8A           1.45 Ang.
PLAT335_ALERT_2_G Check Large C6 Ring    C-C Range C1     -C8A           0.15 Ang.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         13 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         17 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
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  12 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
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   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


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PUBL024_ALERT_1_A The number of authors is greater than 5.
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Computing details

Data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell refinement: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

2-Bromo-1,4-dihydronaphthalene-1,4-dione–1,8-dihydroxy-9,10-dihydroanthracene-9,10-dione (1/1)

Crystal data

C10H5BrO2·C14H8O4	F(000) = 960
Mr = 477.25	Dx = 1.700 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 17.55090 (12) Å	Cell parameters from 22842 reflections
b = 4.85939 (3) Å	θ = 2.6–69.9°
c = 22.83423 (16) Å	µ = 3.39 mm^−1
β = 106.7429 (7)°	T = 100 K
V = 1864.90 (2) Å^3	Plate, orange
Z = 4	0.42 × 0.05 × 0.03 mm

Data collection

Rigaku Saturn724+ (2x2 bin mode) diffractometer	3507 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	3489 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scans	θmax = 70.2°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku Oxford Diffraction, 2015)	h = −21→21
Tmin = 0.697, Tmax = 1.000	k = −5→4
27708 measured reflections	l = −27→27

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.025	w = 1/[σ^2(Fo^2) + (0.0507P)^2 + 1.0878P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.075	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.39 e Å^−3
3507 reflections	Δρmin = −0.32 e Å^−3
286 parameters

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	0.03352 (2)	0.06602 (3)	0.19884 (2)	0.02850 (9)
O1	−0.00432 (7)	0.4511 (2)	0.08868 (6)	0.0283 (3)
O4	0.30880 (7)	0.4406 (2)	0.20139 (5)	0.0240 (3)
C1	0.06668 (9)	0.4618 (3)	0.11528 (7)	0.0212 (3)
C2	0.10318 (9)	0.2887 (3)	0.17016 (7)	0.0212 (3)
C3	0.18140 (9)	0.2861 (3)	0.19828 (7)	0.0220 (3)
H3	0.2015	0.1702	0.2328	0.026*
C4	0.23713 (9)	0.4592 (3)	0.17689 (7)	0.0193 (3)
C4A	0.20374 (8)	0.6514 (3)	0.12522 (6)	0.0189 (3)
C5	0.25340 (9)	0.8282 (3)	0.10564 (7)	0.0221 (3)
H5	0.3089	0.8299	0.1259	0.027*
C6	0.22192 (10)	1.0033 (4)	0.05623 (7)	0.0255 (3)
H6	0.2558	1.1259	0.0431	0.031*
C7	0.14060 (11)	0.9984 (4)	0.02611 (8)	0.0271 (3)
H7	0.1192	1.1172	−0.0077	0.032*
C8	0.09098 (9)	0.8207 (3)	0.04535 (7)	0.0248 (3)
H8	0.0357	0.8171	0.0244	0.030*
C8A	0.12158 (9)	0.6468 (3)	0.09523 (7)	0.0198 (3)
O11	0.36741 (7)	−0.0561 (2)	0.48553 (5)	0.0244 (3)
H11O	0.4113 (8)	0.004 (5)	0.4841 (10)	0.037*
O18	0.58338 (6)	0.5207 (3)	0.42739 (5)	0.0245 (2)
H18O	0.5660 (13)	0.396 (4)	0.4450 (9)	0.037*
O19	0.47299 (6)	0.2395 (2)	0.45660 (5)	0.0217 (2)
O20	0.24399 (6)	0.7932 (2)	0.29021 (5)	0.0261 (2)
C11	0.31370 (9)	0.0927 (3)	0.44373 (7)	0.0199 (3)
C12	0.23328 (10)	0.0292 (3)	0.43377 (7)	0.0229 (3)
H12	0.2184	−0.1123	0.4570	0.027*
C13	0.17525 (9)	0.1711 (4)	0.39025 (7)	0.0251 (3)
H13	0.1208	0.1253	0.3837	0.030*
C14	0.19585 (9)	0.3800 (4)	0.35607 (7)	0.0234 (3)
H14	0.1556	0.4771	0.3265	0.028*
C15	0.40221 (10)	0.9337 (3)	0.30130 (7)	0.0230 (3)
H15	0.3619	1.0299	0.2716	0.028*
C16	0.48208 (11)	0.9953 (4)	0.30923 (7)	0.0251 (3)
H16	0.4960	1.1350	0.2851	0.030*
C17	0.54127 (9)	0.8551 (3)	0.35188 (7)	0.0236 (3)
H17	0.5955	0.8990	0.3568	0.028*
C18	0.52207 (9)	0.6495 (3)	0.38783 (7)	0.0206 (3)
C19	0.41987 (9)	0.3695 (3)	0.41798 (6)	0.0183 (3)
C20	0.29639 (9)	0.6680 (3)	0.32790 (6)	0.0200 (3)
C21	0.38191 (9)	0.7318 (3)	0.33688 (7)	0.0197 (3)
C22	0.44137 (9)	0.5846 (3)	0.38098 (7)	0.0179 (3)
C23	0.33587 (8)	0.3038 (3)	0.40931 (6)	0.0180 (3)
C24	0.27558 (9)	0.4463 (3)	0.36537 (7)	0.0193 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02564 (12)	0.02819 (13)	0.03685 (13)	−0.00434 (6)	0.01723 (9)	−0.00040 (6)
O1	0.0168 (5)	0.0350 (7)	0.0321 (6)	0.0009 (4)	0.0054 (5)	−0.0024 (5)
O4	0.0182 (5)	0.0298 (7)	0.0237 (5)	0.0035 (4)	0.0055 (4)	0.0024 (4)
C1	0.0180 (7)	0.0225 (8)	0.0239 (7)	0.0026 (6)	0.0072 (6)	−0.0046 (6)
C2	0.0216 (7)	0.0202 (7)	0.0250 (7)	−0.0003 (6)	0.0118 (6)	−0.0018 (6)
C3	0.0239 (7)	0.0212 (7)	0.0220 (7)	0.0032 (6)	0.0085 (6)	0.0019 (6)
C4	0.0194 (7)	0.0199 (8)	0.0194 (7)	0.0020 (6)	0.0070 (6)	−0.0017 (5)
C4A	0.0179 (7)	0.0195 (7)	0.0201 (7)	0.0035 (6)	0.0066 (5)	−0.0010 (6)
C5	0.0211 (7)	0.0226 (8)	0.0242 (7)	0.0031 (6)	0.0091 (6)	−0.0004 (6)
C6	0.0303 (9)	0.0227 (7)	0.0277 (8)	0.0036 (7)	0.0151 (7)	0.0023 (7)
C7	0.0327 (9)	0.0261 (8)	0.0242 (8)	0.0094 (7)	0.0111 (7)	0.0046 (7)
C8	0.0233 (7)	0.0269 (8)	0.0229 (7)	0.0067 (6)	0.0049 (6)	0.0016 (6)
C8A	0.0180 (7)	0.0205 (7)	0.0212 (7)	0.0038 (6)	0.0064 (5)	−0.0019 (6)
O11	0.0228 (6)	0.0244 (6)	0.0265 (6)	−0.0019 (4)	0.0077 (5)	0.0069 (4)
O18	0.0180 (5)	0.0250 (6)	0.0315 (6)	−0.0010 (5)	0.0086 (4)	0.0047 (5)
O19	0.0182 (5)	0.0232 (5)	0.0233 (5)	0.0006 (4)	0.0052 (4)	0.0045 (4)
O20	0.0241 (5)	0.0279 (6)	0.0257 (5)	0.0058 (5)	0.0061 (4)	0.0049 (5)
C11	0.0211 (8)	0.0196 (7)	0.0193 (7)	−0.0003 (6)	0.0064 (6)	−0.0039 (5)
C12	0.0241 (8)	0.0239 (8)	0.0241 (7)	−0.0051 (6)	0.0125 (6)	−0.0023 (6)
C13	0.0186 (7)	0.0298 (9)	0.0294 (8)	−0.0038 (6)	0.0109 (6)	−0.0055 (7)
C14	0.0190 (7)	0.0272 (8)	0.0235 (7)	0.0019 (6)	0.0053 (6)	−0.0030 (6)
C15	0.0293 (8)	0.0195 (8)	0.0220 (7)	0.0024 (6)	0.0100 (6)	0.0006 (5)
C16	0.0352 (8)	0.0202 (7)	0.0253 (8)	−0.0024 (7)	0.0172 (7)	0.0009 (7)
C17	0.0233 (7)	0.0238 (8)	0.0280 (8)	−0.0037 (6)	0.0144 (6)	−0.0035 (7)
C18	0.0210 (7)	0.0195 (7)	0.0228 (7)	−0.0002 (6)	0.0088 (6)	−0.0039 (6)
C19	0.0196 (7)	0.0176 (7)	0.0185 (7)	0.0002 (6)	0.0066 (5)	−0.0032 (6)
C20	0.0226 (7)	0.0196 (7)	0.0184 (7)	0.0021 (6)	0.0068 (6)	−0.0016 (6)
C21	0.0225 (7)	0.0184 (7)	0.0197 (7)	0.0006 (6)	0.0085 (5)	−0.0019 (6)
C22	0.0194 (7)	0.0172 (7)	0.0190 (7)	−0.0005 (5)	0.0083 (6)	−0.0022 (5)
C23	0.0185 (7)	0.0179 (7)	0.0187 (6)	−0.0006 (6)	0.0072 (5)	−0.0020 (5)
C24	0.0196 (7)	0.0201 (8)	0.0195 (7)	0.0004 (5)	0.0074 (6)	−0.0026 (5)

Geometric parameters (Å, º)

Br1—C2	1.8857 (15)	O20—C20	1.2248 (18)
O1—C1	1.220 (2)	C11—C12	1.398 (2)
O4—C4	1.2239 (19)	C11—C23	1.413 (2)
C1—C8A	1.483 (2)	C12—C13	1.385 (2)
C1—C2	1.492 (2)	C12—H12	0.9500
C2—C3	1.338 (2)	C13—C14	1.390 (2)
C3—C4	1.476 (2)	C13—H13	0.9500
C3—H3	0.9500	C14—C24	1.391 (2)
C4—C4A	1.486 (2)	C14—H14	0.9500
C4A—C5	1.386 (2)	C15—C21	1.384 (2)
C4A—C8A	1.407 (2)	C15—C16	1.393 (2)
C5—C6	1.394 (2)	C15—H15	0.9500
C5—H5	0.9500	C16—C17	1.382 (2)
C6—C7	1.395 (2)	C16—H16	0.9500
C6—H6	0.9500	C17—C18	1.395 (2)
C7—C8	1.385 (3)	C17—H17	0.9500
C7—H7	0.9500	C18—C22	1.415 (2)
C8—C8A	1.395 (2)	C19—C22	1.460 (2)
C8—H8	0.9500	C19—C23	1.465 (2)
O11—C11	1.3433 (19)	C20—C24	1.485 (2)
O11—H11O	0.833 (10)	C20—C21	1.488 (2)
O18—C18	1.3436 (19)	C21—C22	1.417 (2)
O18—H18O	0.831 (10)	C23—C24	1.412 (2)
O19—C19	1.2541 (18)
O1—C1—C8A	122.25 (15)	C11—C12—H12	119.8
O1—C1—C2	121.59 (15)	C12—C13—C14	120.66 (14)
C8A—C1—C2	116.16 (13)	C12—C13—H13	119.7
C3—C2—C1	122.79 (14)	C14—C13—H13	119.7
C3—C2—Br1	120.42 (12)	C24—C14—C13	119.74 (14)
C1—C2—Br1	116.79 (11)	C24—C14—H14	120.1
C2—C3—C4	121.47 (14)	C13—C14—H14	120.1
C2—C3—H3	119.3	C21—C15—C16	119.69 (15)
C4—C3—H3	119.3	C21—C15—H15	120.2
O4—C4—C3	119.89 (14)	C16—C15—H15	120.2
O4—C4—C4A	121.84 (14)	C17—C16—C15	120.65 (15)
C3—C4—C4A	118.26 (13)	C17—C16—H16	119.7
C5—C4A—C8A	120.29 (14)	C15—C16—H16	119.7
C5—C4A—C4	120.30 (13)	C16—C17—C18	120.53 (15)
C8A—C4A—C4	119.38 (14)	C16—C17—H17	119.7
C4A—C5—C6	119.99 (14)	C18—C17—H17	119.7
C4A—C5—H5	120.0	O18—C18—C17	116.53 (14)
C6—C5—H5	120.0	O18—C18—C22	123.57 (14)
C7—C6—C5	119.96 (16)	C17—C18—C22	119.90 (14)
C7—C6—H6	120.0	O19—C19—C22	120.26 (13)
C5—C6—H6	120.0	O19—C19—C23	120.02 (14)
C8—C7—C6	120.14 (15)	C22—C19—C23	119.71 (13)
C8—C7—H7	119.9	O20—C20—C24	120.36 (14)
C6—C7—H7	119.9	O20—C20—C21	121.12 (14)
C7—C8—C8A	120.47 (15)	C24—C20—C21	118.52 (13)
C7—C8—H8	119.8	C15—C21—C22	120.88 (14)
C8A—C8—H8	119.8	C15—C21—C20	119.13 (14)
C8—C8A—C4A	119.15 (15)	C22—C21—C20	119.99 (14)
C8—C8A—C1	119.16 (14)	C18—C22—C21	118.35 (14)
C4A—C8A—C1	121.69 (14)	C18—C22—C19	120.85 (14)
C11—O11—H11O	104.5 (16)	C21—C22—C19	120.80 (14)
C18—O18—H18O	109.2 (16)	C24—C23—C11	118.74 (13)
O11—C11—C12	117.75 (14)	C24—C23—C19	120.53 (13)
O11—C11—C23	122.46 (14)	C11—C23—C19	120.71 (13)
C12—C11—C23	119.78 (14)	C14—C24—C23	120.66 (14)
C13—C12—C11	120.41 (15)	C14—C24—C20	118.90 (14)
C13—C12—H12	119.8	C23—C24—C20	120.44 (13)
O1—C1—C2—C3	176.47 (15)	C16—C15—C21—C20	−179.96 (14)
C8A—C1—C2—C3	−3.6 (2)	O20—C20—C21—C15	−0.9 (2)
O1—C1—C2—Br1	−3.0 (2)	C24—C20—C21—C15	178.56 (13)
C8A—C1—C2—Br1	176.89 (11)	O20—C20—C21—C22	179.75 (14)
C1—C2—C3—C4	0.7 (2)	C24—C20—C21—C22	−0.8 (2)
Br1—C2—C3—C4	−179.76 (11)	O18—C18—C22—C21	−178.89 (14)
C2—C3—C4—O4	−175.82 (15)	C17—C18—C22—C21	0.4 (2)
C2—C3—C4—C4A	3.7 (2)	O18—C18—C22—C19	0.5 (2)
O4—C4—C4A—C5	−3.8 (2)	C17—C18—C22—C19	179.80 (14)
C3—C4—C4A—C5	176.67 (14)	C15—C21—C22—C18	0.1 (2)
O4—C4—C4A—C8A	174.35 (14)	C20—C21—C22—C18	179.47 (13)
C3—C4—C4A—C8A	−5.2 (2)	C15—C21—C22—C19	−179.30 (14)
C8A—C4A—C5—C6	0.3 (2)	C20—C21—C22—C19	0.1 (2)
C4—C4A—C5—C6	178.50 (14)	O19—C19—C22—C18	0.2 (2)
C4A—C5—C6—C7	−0.7 (2)	C23—C19—C22—C18	−179.10 (13)
C5—C6—C7—C8	0.3 (3)	O19—C19—C22—C21	179.56 (13)
C6—C7—C8—C8A	0.5 (3)	C23—C19—C22—C21	0.3 (2)
C7—C8—C8A—C4A	−0.9 (2)	O11—C11—C23—C24	178.68 (13)
C7—C8—C8A—C1	179.08 (15)	C12—C11—C23—C24	0.0 (2)
C5—C4A—C8A—C8	0.5 (2)	O11—C11—C23—C19	0.1 (2)
C4—C4A—C8A—C8	−177.71 (14)	C12—C11—C23—C19	−178.57 (14)
C5—C4A—C8A—C1	−179.51 (14)	O19—C19—C23—C24	−179.12 (13)
C4—C4A—C8A—C1	2.3 (2)	C22—C19—C23—C24	0.2 (2)
O1—C1—C8A—C8	1.9 (2)	O19—C19—C23—C11	−0.6 (2)
C2—C1—C8A—C8	−178.02 (14)	C22—C19—C23—C11	178.72 (13)
O1—C1—C8A—C4A	−178.11 (15)	C13—C14—C24—C23	−0.1 (2)
C2—C1—C8A—C4A	2.0 (2)	C13—C14—C24—C20	179.34 (14)
O11—C11—C12—C13	−178.50 (14)	C11—C23—C24—C14	−0.1 (2)
C23—C11—C12—C13	0.2 (2)	C19—C23—C24—C14	178.52 (14)
C11—C12—C13—C14	−0.4 (2)	C11—C23—C24—C20	−179.52 (13)
C12—C13—C14—C24	0.4 (2)	C19—C23—C24—C20	−0.9 (2)
C21—C15—C16—C17	0.6 (2)	O20—C20—C24—C14	1.2 (2)
C15—C16—C17—C18	−0.1 (2)	C21—C20—C24—C14	−178.20 (13)
C16—C17—C18—O18	178.93 (14)	O20—C20—C24—C23	−179.31 (14)
C16—C17—C18—C22	−0.4 (2)	C21—C20—C24—C23	1.3 (2)
C16—C15—C21—C22	−0.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11O···O19	0.83 (2)	1.81 (2)	2.5766 (16)	153 (2)
O18—H18O···O19	0.83 (2)	1.89 (2)	2.6097 (16)	144 (2)
O11—H11O···O19^i	0.83 (2)	2.40 (2)	2.8730 (16)	117 (2)
O18—H18O···O11^i	0.83 (2)	2.35 (2)	2.9677 (17)	131 (2)
C3—H3···O20^ii	0.95	2.25	3.1657 (18)	161
C13—H13···O1^iii	0.95	2.46	3.348 (2)	156
C15—H15···O4^iv	0.95	2.56	3.4358 (18)	153
C17—H17···O4^v	0.95	2.43	3.228 (2)	141

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