1-Propyl­quinolinium triiodidocuprate(I)

Wang, Y.J.; Li, H.H.; Chen, Z.R.; Huang, C.C.; Liu, J.B.

doi:10.1107/S1600536807049136

1-Propylquinolinium triiodidocuprate(I)

Y. J. Wang, H. H. Li, Z. R. Chen, C. C. Huang and J. B. Liu

In the title compound, (C₁₂H₁₄N)₂[CuI₃], the asymmetric unit contains two N-propylquinolinium cations which lie on opposite sides of the CuI₃²⁻ anion. In the anion, Cu—I bond distances lie in the range 2.5161 (13)–2.5529 (12) Å. All of the atoms in the anion are essentially coplanar, with an r.m.s. deviation from the [CuI₃]²⁻ mean plane of 0.0001 Å. In the crystal structure, an extensive network of C—H

I hydrogen bonds links the cations and anions into an extended three-dimensional network, with the cations further aggregated through π–π stacking interactions [centroid–centroid distances 3.48 (7) and 3.43 (5) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049136/sj2354sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049136/sj2354Isup2.hkl Contains datablock I

CCDC reference: 655864

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.012 Å
R factor = 0.043
wR factor = 0.149
Data-to-parameter ratio = 22.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.60 Ratio
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         12
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10A   ..  I2      ..       3.09 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18    ..  I1      ..       3.08 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  I3      ..       3.16 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C12 H14 N

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (1)       0.96

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

In the title compound, (I) Fig. 1, the asymmetric unit contains two N-propylquinolinium cations which lie on opposite sides of the CuI₃^2- anion. In the anion cluster, Cu—I bond distances lie in the range from 2.5161 (13) Å to 2.5529 (12)Å and the I1—Cu—I2, I2—Cu—I3 and I1—Cu—I3 bond angles are 124.29°, 117.02° and 118.69°, respectively. All of the atoms in the anion are essentially coplanar with an rms deviation from the [CuI₃]^2- mean plane of 0.0001|%A. The inorganic and organic components are linked via C—H···I hydrogen bonds to give a 3-dimensional network, Table 1. The cations are further aggregated through π-π stacking interactions with centroid to centroid distances of 3.48 (7)Å and 3.43 (5)Å respectively between the quinolinium rings, Fig 2.

Related literature top

For information on C—H···I hydrogen bonds, see Horn et al., 2003 and on π–π stacking, see Robin et al., 2001 Reference not in list – should this be Robin & Fromm (2006)?. For related literature, see: Huang & Xie (1988); Robin & Fromm (2006).

Experimental top

1-propylquinolinium iodide was prepared as reported in literature (Huang et al., 1988). 1-propylquinolinium iodide (0.30 g, 1.0 mmol) and CuI (0.19 g, 1 mmol) were dissolved in 15 mL DMF and stirred for 20 min to give a clear red solution which was filtered and allowed to evaporate at room temperature. Red block-like crystals formed over one, week in 65% yield. (0.32 g). Calcd. For C₂₄H₂₈CuI₃N₂ (788.73): C, 36.40 H, 3.52 N, 3.53% Found: C, 36.51 H, 3.55 N, 3.55%.

Structure description top

Computing details top

Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY (Molecular Structure Corporation, 1999); data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. The structure of (I) showing the atom numbering with ellipsoids drawn at the 50% probability level.
	Fig. 2. Crystal packing for (I) with hydrogen bonds drawn as dashed lines.

1-Propylquinolinium triiodidocuprate(I) top

Crystal data top

(C₁₂H₁₄N)₂[CuI₃]	Z = 2
M_r = 788.73	F(000) = 748.0
Triclinic, P1	D_x = 1.945 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4373 (19) Å	Cell parameters from 18 reflections
b = 9.5500 (19) Å	θ = 12–15°
c = 16.175 (3) Å	µ = 4.26 mm⁻¹
α = 81.27 (3)°	T = 293 K
β = 76.03 (3)°	Block, red
γ = 72.82 (3)°	0.20 × 0.18 × 0.16 mm
V = 1346.4 (5) Å³

Data collection top

Rigaku R-AXIS RAPID Imaging Plate diffractometer	6176 independent reflections
Radiation source: rotor target	4121 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)	h = −12→12
T_min = 0.443, T_max = 0.506	k = −12→12
12812 measured reflections	l = −21→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.149	w = 1/[σ²(F_o²) + (0.0369P)²] where P = (F_o² + 2F_c²)/3
S = 0.87	(Δ/σ)_max = 0.001
6176 reflections	Δρ_max = 0.69 e Å⁻³
273 parameters	Δρ_min = −1.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0010 (2)

Crystal data top

(C₁₂H₁₄N)₂[CuI₃]	γ = 72.82 (3)°
M_r = 788.73	V = 1346.4 (5) Å³
Triclinic, P1	Z = 2
a = 9.4373 (19) Å	Mo Kα radiation
b = 9.5500 (19) Å	µ = 4.26 mm⁻¹
c = 16.175 (3) Å	T = 293 K
α = 81.27 (3)°	0.20 × 0.18 × 0.16 mm
β = 76.03 (3)°

Data collection top

Rigaku R-AXIS RAPID Imaging Plate diffractometer	6176 independent reflections
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)	4121 reflections with I > 2σ(I)
T_min = 0.443, T_max = 0.506	R_int = 0.052
12812 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 0.87	Δρ_max = 0.69 e Å⁻³
6176 reflections	Δρ_min = −1.16 e Å⁻³
273 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.55819 (5)	−0.00607 (5)	0.24539 (3)	0.05558 (16)
I2	0.40382 (5)	0.46869 (5)	0.18593 (3)	0.05692 (16)
I3	0.09917 (5)	0.25384 (6)	0.36757 (3)	0.06252 (17)
Cu1	0.35344 (9)	0.23210 (9)	0.26816 (5)	0.0511 (2)
N2	−0.2782 (5)	0.2353 (6)	0.5522 (3)	0.0471 (12)
N1	0.8453 (5)	0.2573 (6)	0.0483 (3)	0.0459 (11)
C1	0.8245 (8)	0.2374 (8)	0.1316 (5)	0.0577 (17)
H1	0.7371	0.2131	0.1627	0.069*
C2	0.9279 (9)	0.2515 (10)	0.1745 (5)	0.067 (2)
H2	0.9104	0.2371	0.2338	0.081*
C3	1.0563 (9)	0.2868 (9)	0.1292 (5)	0.0648 (19)
H3	1.1266	0.2971	0.1578	0.078*
C4	1.0827 (7)	0.3074 (7)	0.0405 (5)	0.0508 (15)
C5	1.2143 (8)	0.3423 (8)	−0.0111 (6)	0.0625 (19)
H5	1.2860	0.3564	0.0150	0.075*
C6	1.2376 (9)	0.3554 (9)	−0.0963 (6)	0.073 (2)
H6	1.3282	0.3712	−0.1287	0.087*
C7	1.1263 (9)	0.3454 (9)	−0.1371 (5)	0.067 (2)
H7	1.1419	0.3597	−0.1964	0.080*
C8	0.9949 (8)	0.3150 (8)	−0.0912 (5)	0.0538 (16)
H8	0.9211	0.3096	−0.1188	0.065*
C9	0.9736 (6)	0.2920 (6)	−0.0016 (4)	0.0422 (13)
C10	0.7275 (7)	0.2378 (7)	0.0078 (4)	0.0498 (15)
H10A	0.7120	0.3132	−0.0391	0.060*
H10B	0.6325	0.2504	0.0494	0.060*
C11	0.7708 (8)	0.0875 (8)	−0.0257 (5)	0.0581 (17)
H11A	0.8718	0.0690	−0.0617	0.070*
H11B	0.7723	0.0122	0.0219	0.070*
C12	0.6596 (10)	0.0795 (10)	−0.0766 (7)	0.080 (3)
H12A	0.6887	−0.0160	−0.0973	0.119*
H12B	0.6591	0.1532	−0.1241	0.119*
H12C	0.5600	0.0963	−0.0407	0.119*
C13	−0.3068 (8)	0.1201 (8)	0.5292 (5)	0.0596 (18)
H13	−0.2979	0.0339	0.5655	0.071*
C14	−0.3501 (9)	0.1256 (9)	0.4519 (6)	0.069 (2)
H14	−0.3675	0.0432	0.4364	0.083*
C15	−0.3662 (8)	0.2494 (9)	0.4005 (5)	0.0636 (19)
H15	−0.3962	0.2535	0.3493	0.076*
C16	−0.3382 (7)	0.3746 (8)	0.4227 (4)	0.0539 (16)
C17	−0.3528 (8)	0.5081 (11)	0.3699 (5)	0.070 (2)
H17	−0.3844	0.5166	0.3188	0.084*
C18	−0.3207 (9)	0.6242 (9)	0.3934 (6)	0.071 (2)
H18	−0.3310	0.7119	0.3585	0.085*
C19	−0.2729 (9)	0.6120 (9)	0.4690 (6)	0.070 (2)
H19	−0.2492	0.6920	0.4832	0.084*
C20	−0.2590 (7)	0.4888 (8)	0.5234 (5)	0.0540 (16)
H20	−0.2290	0.4847	0.5746	0.065*
C21	−0.2914 (6)	0.3660 (7)	0.5004 (4)	0.0405 (12)
C22	−0.2312 (8)	0.2202 (9)	0.6344 (4)	0.0589 (18)
H22A	−0.2700	0.1451	0.6725	0.071*
H22B	−0.2744	0.3124	0.6607	0.071*
C23	−0.0588 (8)	0.1787 (10)	0.6223 (5)	0.068 (2)
H23A	−0.0150	0.0869	0.5955	0.082*
H23B	−0.0196	0.2543	0.5850	0.082*
C24	−0.0146 (11)	0.1621 (15)	0.7068 (7)	0.104 (4)
H24A	0.0939	0.1359	0.6984	0.157*
H24B	−0.0524	0.0863	0.7433	0.157*
H24C	−0.0569	0.2534	0.7328	0.157*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0505 (3)	0.0452 (3)	0.0663 (3)	−0.01132 (19)	−0.0080 (2)	−0.0006 (2)
I2	0.0560 (3)	0.0485 (3)	0.0628 (3)	−0.0133 (2)	−0.0149 (2)	0.0082 (2)
I3	0.0488 (3)	0.0813 (4)	0.0485 (3)	−0.0122 (2)	−0.00168 (19)	−0.0029 (2)
Cu1	0.0473 (4)	0.0574 (5)	0.0480 (5)	−0.0128 (4)	−0.0118 (3)	−0.0015 (4)
N2	0.037 (2)	0.055 (3)	0.046 (3)	−0.012 (2)	−0.005 (2)	−0.001 (2)
N1	0.039 (2)	0.051 (3)	0.046 (3)	−0.012 (2)	−0.008 (2)	−0.003 (2)
C1	0.061 (4)	0.064 (5)	0.047 (4)	−0.020 (3)	−0.009 (3)	0.004 (3)
C2	0.075 (5)	0.088 (6)	0.040 (4)	−0.027 (4)	−0.016 (3)	0.010 (4)
C3	0.071 (5)	0.066 (5)	0.065 (5)	−0.018 (4)	−0.033 (4)	0.001 (4)
C4	0.051 (3)	0.049 (4)	0.055 (4)	−0.013 (3)	−0.016 (3)	−0.006 (3)
C5	0.043 (3)	0.061 (5)	0.086 (6)	−0.018 (3)	−0.010 (3)	−0.011 (4)
C6	0.056 (4)	0.068 (5)	0.089 (7)	−0.028 (4)	0.016 (4)	−0.018 (4)
C7	0.076 (5)	0.070 (5)	0.047 (4)	−0.025 (4)	0.011 (4)	−0.010 (4)
C8	0.055 (4)	0.055 (4)	0.052 (4)	−0.020 (3)	−0.003 (3)	−0.007 (3)
C9	0.043 (3)	0.035 (3)	0.046 (4)	−0.007 (2)	−0.008 (2)	−0.006 (3)
C10	0.040 (3)	0.057 (4)	0.054 (4)	−0.014 (3)	−0.015 (3)	0.003 (3)
C11	0.057 (4)	0.050 (4)	0.072 (5)	−0.014 (3)	−0.020 (3)	−0.010 (4)
C12	0.074 (5)	0.068 (5)	0.108 (8)	−0.022 (4)	−0.030 (5)	−0.016 (5)
C13	0.055 (4)	0.048 (4)	0.071 (5)	−0.013 (3)	−0.011 (3)	0.006 (3)
C14	0.066 (5)	0.068 (5)	0.087 (6)	−0.023 (4)	−0.028 (4)	−0.018 (5)
C15	0.055 (4)	0.082 (6)	0.058 (5)	−0.017 (4)	−0.013 (3)	−0.021 (4)
C16	0.036 (3)	0.076 (5)	0.045 (4)	−0.013 (3)	−0.004 (2)	−0.006 (3)
C17	0.042 (3)	0.103 (7)	0.052 (5)	−0.014 (4)	−0.011 (3)	0.019 (4)
C18	0.056 (4)	0.064 (5)	0.076 (6)	−0.010 (4)	−0.008 (4)	0.025 (4)
C19	0.053 (4)	0.053 (4)	0.094 (7)	−0.017 (3)	−0.001 (4)	0.003 (4)
C20	0.047 (3)	0.055 (4)	0.060 (4)	−0.014 (3)	−0.006 (3)	−0.011 (3)
C21	0.032 (3)	0.049 (3)	0.039 (3)	−0.014 (2)	−0.003 (2)	−0.001 (3)
C22	0.063 (4)	0.084 (5)	0.032 (3)	−0.024 (4)	−0.014 (3)	0.001 (3)
C23	0.058 (4)	0.085 (6)	0.062 (5)	−0.016 (4)	−0.020 (3)	−0.001 (4)
C24	0.078 (6)	0.161 (11)	0.074 (7)	−0.018 (6)	−0.040 (5)	0.003 (7)

Geometric parameters (Å, º) top

I1—Cu1	2.5213 (14)	C11—H11B	0.9700
I2—Cu1	2.5529 (12)	C12—H12A	0.9600
I3—Cu1	2.5161 (13)	C12—H12B	0.9600
N2—C13	1.331 (9)	C12—H12C	0.9600
N2—C21	1.385 (8)	C13—C14	1.396 (11)
N2—C22	1.474 (8)	C13—H13	0.9300
N1—C1	1.306 (9)	C14—C15	1.330 (12)
N1—C9	1.382 (8)	C14—H14	0.9300
N1—C10	1.487 (7)	C15—C16	1.411 (10)
C1—C2	1.373 (10)	C15—H15	0.9300
C1—H1	0.9300	C16—C21	1.413 (9)
C2—C3	1.362 (11)	C16—C17	1.414 (11)
C2—H2	0.9300	C17—C18	1.358 (12)
C3—C4	1.390 (11)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.381 (12)
C4—C9	1.414 (8)	C18—H18	0.9300
C4—C5	1.418 (10)	C19—C20	1.351 (11)
C5—C6	1.333 (13)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.416 (9)
C6—C7	1.400 (12)	C20—H20	0.9300
C6—H6	0.9300	C22—C23	1.527 (10)
C7—C8	1.370 (10)	C22—H22A	0.9700
C7—H7	0.9300	C22—H22B	0.9700
C8—C9	1.407 (9)	C23—C24	1.496 (11)
C8—H8	0.9300	C23—H23A	0.9700
C10—C11	1.518 (9)	C23—H23B	0.9700
C10—H10A	0.9700	C24—H24A	0.9600
C10—H10B	0.9700	C24—H24B	0.9600
C11—C12	1.506 (10)	C24—H24C	0.9600
C11—H11A	0.9700

I3—Cu1—I1	124.29 (5)	H12A—C12—H12B	109.5
I3—Cu1—I2	117.02 (5)	C11—C12—H12C	109.5
I1—Cu1—I2	118.69 (4)	H12A—C12—H12C	109.5
C13—N2—C21	121.1 (6)	H12B—C12—H12C	109.5
C13—N2—C22	118.3 (6)	N2—C13—C14	121.5 (7)
C21—N2—C22	120.6 (6)	N2—C13—H13	119.3
C1—N1—C9	121.8 (5)	C14—C13—H13	119.3
C1—N1—C10	117.8 (5)	C15—C14—C13	119.6 (7)
C9—N1—C10	120.4 (5)	C15—C14—H14	120.2
N1—C1—C2	121.9 (6)	C13—C14—H14	120.2
N1—C1—H1	119.1	C14—C15—C16	120.8 (7)
C2—C1—H1	119.1	C14—C15—H15	119.6
C3—C2—C1	119.3 (7)	C16—C15—H15	119.6
C3—C2—H2	120.3	C15—C16—C21	118.9 (7)
C1—C2—H2	120.3	C15—C16—C17	122.8 (7)
C2—C3—C4	120.3 (6)	C21—C16—C17	118.3 (7)
C2—C3—H3	119.9	C18—C17—C16	120.4 (7)
C4—C3—H3	119.9	C18—C17—H17	119.8
C3—C4—C9	118.8 (6)	C16—C17—H17	119.8
C3—C4—C5	123.6 (6)	C17—C18—C19	120.1 (7)
C9—C4—C5	117.6 (7)	C17—C18—H18	120.0
C6—C5—C4	121.5 (7)	C19—C18—H18	120.0
C6—C5—H5	119.2	C20—C19—C18	122.8 (8)
C4—C5—H5	119.2	C20—C19—H19	118.6
C5—C6—C7	120.3 (7)	C18—C19—H19	118.6
C5—C6—H6	119.8	C19—C20—C21	118.3 (7)
C7—C6—H6	119.8	C19—C20—H20	120.8
C8—C7—C6	121.2 (8)	C21—C20—H20	120.8
C8—C7—H7	119.4	N2—C21—C16	118.2 (6)
C6—C7—H7	119.4	N2—C21—C20	121.8 (6)
C7—C8—C9	118.8 (7)	C16—C21—C20	120.1 (6)
C7—C8—H8	120.6	N2—C22—C23	111.4 (6)
C9—C8—H8	120.6	N2—C22—H22A	109.3
N1—C9—C8	121.6 (5)	C23—C22—H22A	109.3
N1—C9—C4	117.9 (6)	N2—C22—H22B	109.3
C8—C9—C4	120.5 (6)	C23—C22—H22B	109.3
N1—C10—C11	112.3 (5)	H22A—C22—H22B	108.0
N1—C10—H10A	109.2	C24—C23—C22	110.2 (7)
C11—C10—H10A	109.2	C24—C23—H23A	109.6
N1—C10—H10B	109.2	C22—C23—H23A	109.6
C11—C10—H10B	109.2	C24—C23—H23B	109.6
H10A—C10—H10B	107.9	C22—C23—H23B	109.6
C12—C11—C10	110.6 (6)	H23A—C23—H23B	108.1
C12—C11—H11A	109.5	C23—C24—H24A	109.5
C10—C11—H11A	109.5	C23—C24—H24B	109.5
C12—C11—H11B	109.5	H24A—C24—H24B	109.5
C10—C11—H11B	109.5	C23—C24—H24C	109.5
H11A—C11—H11B	108.1	H24A—C24—H24C	109.5
C11—C12—H12A	109.5	H24B—C24—H24C	109.5
C11—C12—H12B	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···I2ⁱ	0.97	3.09	4.046 (6)	167
C13—H13···I3ⁱⁱ	0.93	3.04	3.871 (6)	150
C18—H18···I1ⁱⁱⁱ	0.93	3.08	3.986 (6)	165
C2—H2···I3^iv	0.93	3.16	3.852 (6)	133

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

Experimental details

Crystal data
Chemical formula	(C₁₂H₁₄N)₂[CuI₃]
M_r	788.73
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.4373 (19), 9.5500 (19), 16.175 (3)
α, β, γ (°)	81.27 (3), 76.03 (3), 72.82 (3)
V (Å³)	1346.4 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.26
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Rigaku R-AXIS RAPID Imaging Plate
Absorption correction	Multi-scan (TEXRAY; Molecular Structure Corporation, 1999)
T_min, T_max	0.443, 0.506
No. of measured, independent and observed [I > 2σ(I)] reflections	12812, 6176, 4121
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.149, 0.87
No. of reflections	6176
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −1.16

Computer programs: TEXRAY (Molecular Structure Corporation, 1999), TEXSAN (Molecular Structure Corporation, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEX (McArdle, 1995).