4,7-Di­bromo­benzo­[c]­fur­azan 1-oxide–pyrene (1/1)

The 1:1 complex of 4,7-di­bromo­benzo­[c]­fur­azan 1-oxide and pyrene, C₆H₂N₂O₂Br₂·C₁₆H₁₀, contains π stacks of alternating mol­ecules. The mol­ecules are tilted by 2.5 (1)° with respect to each other and by 22.6 (1) and 25.0 (1)°, respectively, away from being normal to the direction of the stack. The average intermolecular distances in the stack alternate between 3.45 (2) and 3.49 (2) Å. There are no unusual contacts between adjacent stacks.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.051
• wR factor = 0.127
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.543
           From the CIF: _refine_ls_abs_structure_Flack_su    0.017
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       0.54
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C17    -   C18     ..       5.51 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.28
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         11

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.53
           From the CIF: _reflns_number_total               4132
           Count of symmetry unique reflns         2112
           Completeness (_total/calc)            195.64%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2020
           Fraction of Friedel pairs measured     0.956
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4,7-Dibromobenzo[c]furazan 1-oxide–pyrene (1/1)

Crystal data

C6H2Br2N2O2·C16H10	F(000) = 488
Mr = 496.16	Dx = 1.803 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 2896 reflections
a = 7.851 (2) Å	θ = 2.6–24.4°
b = 7.657 (2) Å	µ = 4.46 mm^−1
c = 16.296 (4) Å	T = 173 K
β = 111.09 (1)°	Irregular plate, yellow
V = 914.0 (4) Å^3	0.45 × 0.30 × 0.15 mm
Z = 2

Data collection

Siemens SMART area-detector diffractometer	4132 independent reflections
Radiation source: fine-focus sealed tube	2968 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
ω scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995)	h = −10→10
Tmin = 0.20, Tmax = 0.51	k = −9→9
10268 measured reflections	l = −20→21

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.059P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
4132 reflections	Δρmax = 0.92 e Å^−3
254 parameters	Δρmin = −0.54 e Å^−3
2 restraints	Absolute structure: The crystal was a racemic twin; see Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.543 (17)

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

	x	y	z	Uiso*/Ueq
Br3	0.80752 (10)	0.70806 (9)	0.42399 (6)	0.0611 (3)
Br6	0.08208 (7)	1.03367 (8)	0.11304 (5)	0.0443 (2)
O1	0.4005 (10)	0.9523 (8)	0.0357 (4)	0.0684 (16)
O2	0.6648 (8)	0.8393 (7)	0.1332 (4)	0.0610 (15)
N1	0.4791 (9)	0.9047 (8)	0.1116 (4)	0.0437 (15)
N2	0.7328 (10)	0.7907 (8)	0.2203 (5)	0.0558 (17)
C1	0.4427 (9)	0.8944 (8)	0.1838 (4)	0.0308 (14)
C2	0.5997 (10)	0.8218 (8)	0.2502 (5)	0.0362 (16)
C3	0.5988 (10)	0.7990 (9)	0.3361 (5)	0.0398 (17)
C4	0.4478 (12)	0.8445 (9)	0.3520 (5)	0.046 (2)
H4	0.4458	0.8310	0.4096	0.056*
C5	0.2913 (11)	0.9123 (9)	0.2842 (5)	0.0393 (17)
H5	0.1860	0.9395	0.2975	0.047*
C6	0.2869 (10)	0.9394 (8)	0.2020 (5)	0.0329 (15)
C11	0.8849 (10)	0.1725 (9)	0.3721 (6)	0.0483 (19)
H11	0.9967	0.1217	0.4088	0.058*
C12	0.7535 (12)	0.2078 (9)	0.4043 (5)	0.042 (2)
H12	0.7741	0.1791	0.4638	0.050*
C13	0.5878 (11)	0.2851 (8)	0.3537 (4)	0.0345 (17)
C14	0.4459 (11)	0.3261 (9)	0.3870 (5)	0.0424 (18)
H14	0.4624	0.2976	0.4461	0.051*
C15	0.2937 (10)	0.4025 (9)	0.3370 (5)	0.0420 (17)
H15	0.2055	0.4315	0.3622	0.050*
C16	0.2547 (9)	0.4439 (8)	0.2460 (5)	0.0363 (17)
C17	0.0918 (10)	0.5232 (9)	0.1913 (6)	0.0477 (19)
H17	−0.0011	0.5538	0.2133	0.057*
C18	0.0700 (17)	0.5559 (8)	0.1035 (7)	0.048 (2)
H18	−0.0403	0.6084	0.0662	0.058*
C19	0.1964 (11)	0.5170 (9)	0.0700 (5)	0.0466 (19)
H19	0.1733	0.5423	0.0099	0.056*
C20	0.3626 (9)	0.4398 (8)	0.1207 (4)	0.0382 (16)
C21	0.5021 (10)	0.3969 (9)	0.0889 (5)	0.0418 (17)
H21	0.4834	0.4212	0.0291	0.050*
C22	0.6596 (12)	0.3236 (9)	0.1390 (5)	0.0473 (18)
H22	0.7492	0.2961	0.1145	0.057*
C23	0.6937 (9)	0.2860 (8)	0.2302 (5)	0.0373 (15)
C24	0.8569 (10)	0.2103 (8)	0.2857 (6)	0.0451 (17)
H24	0.9502	0.1846	0.2633	0.054*
C25	0.5596 (9)	0.3248 (8)	0.2645 (4)	0.0309 (15)
C26	0.3911 (9)	0.4040 (7)	0.2101 (4)	0.0304 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br3	0.0595 (5)	0.0323 (4)	0.0587 (5)	−0.0013 (4)	−0.0185 (4)	0.0045 (4)
Br6	0.0410 (4)	0.0316 (3)	0.0452 (4)	0.0024 (3)	−0.0026 (3)	−0.0025 (3)
O1	0.096 (5)	0.063 (4)	0.048 (4)	−0.002 (3)	0.028 (3)	−0.005 (3)
O2	0.071 (4)	0.054 (3)	0.070 (4)	0.001 (3)	0.040 (3)	−0.007 (3)
N1	0.057 (4)	0.037 (3)	0.039 (4)	−0.003 (3)	0.020 (3)	−0.008 (3)
N2	0.061 (4)	0.039 (4)	0.064 (5)	0.003 (3)	0.019 (4)	−0.005 (3)
C1	0.037 (4)	0.020 (3)	0.031 (4)	0.000 (3)	0.007 (3)	−0.006 (2)
C2	0.038 (4)	0.023 (3)	0.042 (4)	−0.004 (3)	0.007 (3)	−0.013 (3)
C3	0.039 (4)	0.026 (3)	0.039 (4)	−0.005 (3)	−0.005 (3)	−0.001 (3)
C4	0.066 (5)	0.041 (4)	0.028 (4)	−0.016 (4)	0.010 (4)	0.002 (3)
C5	0.043 (4)	0.032 (3)	0.044 (4)	−0.002 (3)	0.017 (3)	0.002 (3)
C6	0.034 (4)	0.023 (3)	0.036 (4)	−0.004 (3)	0.006 (3)	−0.001 (3)
C11	0.037 (4)	0.034 (4)	0.057 (5)	0.000 (3)	−0.003 (4)	0.007 (3)
C12	0.053 (5)	0.028 (4)	0.035 (5)	−0.009 (3)	0.003 (4)	0.005 (3)
C13	0.047 (4)	0.020 (3)	0.028 (3)	−0.009 (3)	0.003 (3)	−0.004 (2)
C14	0.061 (5)	0.039 (4)	0.026 (3)	−0.014 (3)	0.014 (4)	−0.001 (3)
C15	0.049 (4)	0.040 (4)	0.044 (4)	−0.010 (3)	0.025 (4)	−0.016 (3)
C16	0.040 (4)	0.024 (3)	0.037 (4)	−0.010 (3)	0.005 (3)	−0.011 (3)
C17	0.034 (4)	0.029 (3)	0.074 (6)	0.001 (3)	0.012 (4)	−0.009 (3)
C18	0.064 (6)	0.029 (4)	0.034 (5)	−0.001 (4)	−0.003 (4)	−0.002 (3)
C19	0.056 (5)	0.034 (4)	0.037 (4)	−0.013 (3)	0.000 (4)	0.005 (3)
C20	0.047 (4)	0.028 (3)	0.030 (3)	−0.016 (3)	0.001 (3)	−0.004 (3)
C21	0.053 (4)	0.042 (4)	0.034 (4)	−0.019 (3)	0.019 (3)	−0.004 (3)
C22	0.058 (5)	0.040 (4)	0.043 (4)	−0.008 (3)	0.016 (4)	−0.004 (3)
C23	0.036 (3)	0.027 (3)	0.045 (4)	−0.009 (3)	0.009 (3)	−0.004 (3)
C24	0.034 (3)	0.031 (3)	0.071 (5)	−0.007 (3)	0.021 (4)	−0.009 (3)
C25	0.036 (4)	0.019 (3)	0.034 (4)	−0.011 (2)	0.008 (3)	−0.006 (2)
C26	0.036 (3)	0.015 (2)	0.032 (3)	−0.009 (2)	0.002 (3)	−0.003 (2)

Geometric parameters (Å, º)

Br3—C3	1.879 (7)	C14—C15	1.317 (11)
Br6—C6	1.879 (7)	C14—H14	0.9500
O1—N1	1.223 (9)	C15—C16	1.437 (10)
O2—N2	1.376 (9)	C15—H15	0.9500
O2—N1	1.460 (8)	C16—C17	1.407 (10)
N1—C1	1.308 (9)	C16—C26	1.426 (10)
N2—C2	1.323 (10)	C17—C18	1.401 (14)
C1—C6	1.402 (10)	C17—H17	0.9500
C1—C2	1.428 (10)	C18—C19	1.327 (16)
C2—C3	1.414 (11)	C18—H18	0.9500
C3—C4	1.347 (12)	C19—C20	1.400 (10)
C4—C5	1.423 (11)	C19—H19	0.9500
C4—H4	0.9500	C20—C21	1.409 (10)
C5—C6	1.343 (10)	C20—C26	1.419 (9)
C5—H5	0.9500	C21—C22	1.335 (10)
C11—C12	1.342 (13)	C21—H21	0.9500
C11—C24	1.374 (12)	C22—C23	1.441 (11)
C11—H11	0.9500	C22—H22	0.9500
C12—C13	1.397 (11)	C23—C25	1.391 (10)
C12—H12	0.9500	C23—C24	1.401 (10)
C13—C25	1.421 (9)	C24—H24	0.9500
C13—C14	1.439 (11)	C25—C26	1.435 (9)
N2—O2—N1	108.9 (5)	C14—C15—H15	118.5
O1—N1—C1	137.2 (7)	C16—C15—H15	118.5
O1—N1—O2	116.2 (6)	C17—C16—C26	118.5 (7)
C1—N1—O2	106.6 (5)	C17—C16—C15	123.8 (7)
C2—N2—O2	105.5 (7)	C26—C16—C15	117.6 (6)
N1—C1—C6	131.7 (6)	C18—C17—C16	118.3 (8)
N1—C1—C2	107.2 (6)	C18—C17—H17	120.9
C6—C1—C2	121.1 (7)	C16—C17—H17	120.9
N2—C2—C3	128.9 (7)	C19—C18—C17	123.1 (9)
N2—C2—C1	111.8 (7)	C19—C18—H18	118.5
C3—C2—C1	119.2 (7)	C17—C18—H18	118.5
C4—C3—C2	118.5 (7)	C18—C19—C20	121.9 (8)
C4—C3—Br3	122.4 (6)	C18—C19—H19	119.1
C2—C3—Br3	119.1 (6)	C20—C19—H19	119.1
C3—C4—C5	121.2 (7)	C19—C20—C21	124.4 (7)
C3—C4—H4	119.4	C19—C20—C26	117.2 (7)
C5—C4—H4	119.4	C21—C20—C26	118.4 (6)
C6—C5—C4	122.4 (7)	C22—C21—C20	123.0 (7)
C6—C5—H5	118.8	C22—C21—H21	118.5
C4—C5—H5	118.8	C20—C21—H21	118.5
C5—C6—C1	117.5 (7)	C21—C22—C23	120.1 (7)
C5—C6—Br6	122.4 (6)	C21—C22—H22	119.9
C1—C6—Br6	120.0 (5)	C23—C22—H22	119.9
C12—C11—C24	119.7 (7)	C25—C23—C24	118.5 (7)
C12—C11—H11	120.1	C25—C23—C22	119.0 (7)
C24—C11—H11	120.1	C24—C23—C22	122.4 (7)
C11—C12—C13	122.5 (8)	C11—C24—C23	121.4 (7)
C11—C12—H12	118.7	C11—C24—H24	119.3
C13—C12—H12	118.7	C23—C24—H24	119.3
C12—C13—C25	117.7 (7)	C23—C25—C13	120.2 (7)
C12—C13—C14	123.6 (7)	C23—C25—C26	120.3 (6)
C25—C13—C14	118.8 (7)	C13—C25—C26	119.5 (6)
C15—C14—C13	121.2 (7)	C20—C26—C16	121.0 (6)
C15—C14—H14	119.4	C20—C26—C25	119.1 (6)
C13—C14—H14	119.4	C16—C26—C25	119.9 (6)
C14—C15—C16	123.0 (7)