Tetra-n-propyl­ammonium perchlorate

The crystallographic analysis of the title compound, C₁₂H₂₈N⁺·ClO₄⁻, (I), shows that inter­molecular C—H...O inter­actions stabilize the crystal structure. The compound is isomorphous with tetra-n-propyl­ammonium iodide, whose structure has been described by Yoshida et al. [Acta Cryst. (1994). C50, 1758–1760].

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.049
• wR factor = 0.108
• Data-to-parameter ratio = 22.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        Cl1

Author Response: The oxygen atoms in perchlorate anion often show higer U(eq) compared with the chloride atoms located in the center of molecule. The alert is caused by large Ueq of oxygen atoms.

Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?

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           27.90
           From the CIF: _reflns_number_total               3723
           Count of symmetry unique reflns         2130
           Completeness (_total/calc)            174.79%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1593
           Fraction of Friedel pairs measured     0.748
           Are heavy atom types Z>Si present        yes

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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: SMART-W2K/NT (Bruker, 2003); cell refinement: SAINT-W2K/NT (Bruker, 2003); data reduction: SAINT-W2K/NT; program(s) used to solve structure: SHELXTL-NT (Bruker, 2003); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL-NT.

(I)

Crystal data

C12H28N^+·ClO4^−	F(000) = 624
Mr = 285.80	Dx = 1.218 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2126 reflections
a = 13.3335 (9) Å	θ = 2.3–21.6°
b = 12.1528 (8) Å	µ = 0.25 mm^−1
c = 9.6210 (6) Å	T = 173 K
V = 1558.98 (18) Å^3	Needle, colorless
Z = 4	0.48 × 0.21 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3723 independent reflections
Radiation source: fine-focus sealed tube	2851 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
Detector resolution: 8.366 pixels mm^-1	θmax = 27.9°, θmin = 2.3°
φ and ω scans	h = −17→14
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −15→15
Tmin = 0.889, Tmax = 0.951	l = −12→12
11458 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0417P)^2] where P = (Fo^2 + 2Fc^2)/3
3723 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.29 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
O1	0.62769 (17)	0.49229 (17)	0.0345 (3)	0.0729 (7)
O2	0.47890 (18)	0.5683 (2)	0.1123 (2)	0.0751 (8)
O3	0.5084 (2)	0.5547 (2)	−0.1192 (2)	0.0893 (10)
O4	0.59767 (16)	0.67824 (17)	0.0110 (4)	0.1045 (10)
Cl1	0.55488 (4)	0.57450 (4)	0.01051 (6)	0.02855 (15)
C1	0.3800 (2)	0.9238 (2)	−0.1155 (2)	0.0335 (6)
H1A	0.3974	0.9736	−0.1932	0.040*
H1B	0.3093	0.9384	−0.0902	0.040*
C2	0.3879 (2)	0.8059 (2)	−0.1668 (3)	0.0420 (7)
H2A	0.4551	0.7932	−0.2075	0.050*
H2B	0.3791	0.7545	−0.0879	0.050*
C3	0.3083 (2)	0.7848 (3)	−0.2749 (3)	0.0487 (8)
H3A	0.2419	0.7969	−0.2340	0.073*
H3B	0.3133	0.7086	−0.3075	0.073*
H3C	0.3179	0.8350	−0.3534	0.073*
C4	0.4261 (2)	0.8749 (2)	0.1297 (2)	0.0353 (7)
H4A	0.4548	0.8021	0.1068	0.042*
H4B	0.4624	0.9033	0.2121	0.042*
C5	0.3166 (2)	0.8594 (3)	0.1686 (3)	0.0451 (7)
H5A	0.2886	0.9294	0.2042	0.054*
H5B	0.2775	0.8372	0.0857	0.054*
C6	0.3096 (3)	0.7715 (2)	0.2791 (3)	0.0511 (9)
H6A	0.3434	0.7046	0.2466	0.077*
H6B	0.2389	0.7551	0.2980	0.077*
H6C	0.3419	0.7976	0.3644	0.077*
C7	0.42077 (19)	1.07017 (19)	0.0541 (2)	0.0354 (6)
H7A	0.3473	1.0759	0.0670	0.043*
H7B	0.4525	1.0831	0.1457	0.043*
C8	0.4538 (2)	1.1608 (2)	−0.0440 (3)	0.0476 (7)
H8A	0.4221	1.1503	−0.1361	0.057*
H8B	0.5275	1.1582	−0.0562	0.057*
C9	0.4230 (2)	1.27240 (19)	0.0164 (3)	0.0489 (7)
H9A	0.3498	1.2754	0.0253	0.073*
H9B	0.4457	1.3313	−0.0456	0.073*
H9C	0.4537	1.2819	0.1082	0.073*
C10	0.55467 (18)	0.94209 (19)	−0.0352 (2)	0.0343 (6)
H10A	0.5668	0.8650	−0.0640	0.041*
H10B	0.5658	0.9892	−0.1177	0.041*
C11	0.6316 (2)	0.9723 (3)	0.0733 (3)	0.0511 (8)
H11A	0.6249	0.9225	0.1542	0.061*
H11B	0.6195	1.0485	0.1056	0.061*
C12	0.73682 (19)	0.9633 (3)	0.0139 (4)	0.0615 (9)
H12A	0.7483	0.8881	−0.0192	0.092*
H12B	0.7859	0.9812	0.0862	0.092*
H12C	0.7441	1.0148	−0.0638	0.092*
N1	0.44549 (15)	0.95270 (14)	0.0078 (2)	0.0306 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0588 (14)	0.0543 (12)	0.106 (2)	0.0098 (12)	−0.0019 (15)	0.0155 (14)
O2	0.0608 (15)	0.116 (2)	0.0490 (11)	0.0003 (17)	0.0062 (11)	0.0012 (15)
O3	0.114 (2)	0.107 (2)	0.0469 (12)	0.0387 (19)	0.0068 (14)	−0.0079 (14)
O4	0.0567 (15)	0.0458 (12)	0.211 (3)	−0.0001 (11)	0.011 (2)	0.002 (2)
Cl1	0.0288 (3)	0.0269 (2)	0.0299 (3)	0.0043 (3)	0.0051 (3)	0.0032 (3)
C1	0.0361 (14)	0.0353 (13)	0.0291 (12)	0.0024 (14)	−0.0017 (11)	−0.0003 (12)
C2	0.0416 (17)	0.0383 (15)	0.0461 (16)	0.0003 (15)	−0.0046 (14)	−0.0057 (13)
C3	0.046 (2)	0.0534 (19)	0.0467 (18)	−0.0044 (18)	−0.0051 (16)	−0.0110 (16)
C4	0.0414 (18)	0.0340 (13)	0.0305 (13)	0.0029 (14)	−0.0010 (12)	0.0048 (11)
C5	0.0365 (17)	0.0512 (18)	0.0476 (16)	0.0016 (15)	0.0067 (15)	0.0097 (15)
C6	0.055 (2)	0.0492 (19)	0.0491 (19)	−0.0030 (19)	0.0101 (17)	0.0103 (16)
C7	0.0333 (14)	0.0336 (13)	0.0394 (13)	0.0040 (13)	0.0019 (11)	−0.0038 (12)
C8	0.0531 (19)	0.0341 (14)	0.0555 (17)	0.0011 (14)	0.0124 (16)	−0.0011 (13)
C9	0.0537 (18)	0.0316 (13)	0.0615 (19)	−0.0017 (12)	−0.0063 (19)	−0.0026 (15)
C10	0.0276 (12)	0.0324 (13)	0.0429 (14)	0.0000 (12)	0.0045 (12)	−0.0013 (11)
C11	0.0340 (16)	0.0541 (18)	0.065 (2)	0.0021 (16)	−0.0053 (15)	−0.0111 (16)
C12	0.0311 (15)	0.067 (2)	0.087 (2)	−0.0011 (14)	0.002 (2)	0.004 (2)
N1	0.0297 (10)	0.0291 (9)	0.0330 (10)	0.0033 (9)	0.0034 (12)	0.0003 (10)

Geometric parameters (Å, º)

C1—N1	1.515 (3)	C7—H7A	0.9900
C1—C2	1.519 (4)	C7—H7B	0.9900
C1—H1A	0.9900	C8—C9	1.531 (3)
C1—H1B	0.9900	C8—H8A	0.9900
C2—C3	1.508 (4)	C8—H8B	0.9900
C2—H2A	0.9900	C9—H9A	0.9800
C2—H2B	0.9900	C9—H9B	0.9800
C3—H3A	0.9800	C9—H9C	0.9800
C3—H3B	0.9800	C10—C11	1.508 (3)
C3—H3C	0.9800	C10—N1	1.519 (3)
C4—C5	1.519 (4)	C10—H10A	0.9900
C4—N1	1.528 (3)	C10—H10B	0.9900
C4—H4A	0.9900	C11—C12	1.520 (4)
C4—H4B	0.9900	C11—H11A	0.9900
C5—C6	1.511 (4)	C11—H11B	0.9900
C5—H5A	0.9900	C12—H12A	0.9800
C5—H5B	0.9900	C12—H12B	0.9800
C6—H6A	0.9800	C12—H12C	0.9800
C6—H6B	0.9800	O1—Cl1	1.412 (2)
C6—H6C	0.9800	O2—Cl1	1.411 (2)
C7—C8	1.516 (4)	O3—Cl1	1.414 (2)
C7—N1	1.531 (3)	O4—Cl1	1.384 (2)
N1—C1—C2	115.7 (2)	C7—C8—C9	109.2 (2)
N1—C1—H1A	108.4	C7—C8—H8A	109.8
C2—C1—H1A	108.4	C9—C8—H8A	109.8
N1—C1—H1B	108.4	C7—C8—H8B	109.8
C2—C1—H1B	108.4	C9—C8—H8B	109.8
H1A—C1—H1B	107.4	H8A—C8—H8B	108.3
C3—C2—C1	109.6 (2)	C8—C9—H9A	109.5
C3—C2—H2A	109.7	C8—C9—H9B	109.5
C1—C2—H2A	109.7	H9A—C9—H9B	109.5
C3—C2—H2B	109.7	C8—C9—H9C	109.5
C1—C2—H2B	109.7	H9A—C9—H9C	109.5
H2A—C2—H2B	108.2	H9B—C9—H9C	109.5
C2—C3—H3A	109.5	C11—C10—N1	116.2 (2)
C2—C3—H3B	109.5	C11—C10—H10A	108.2
H3A—C3—H3B	109.5	N1—C10—H10A	108.2
C2—C3—H3C	109.5	C11—C10—H10B	108.2
H3A—C3—H3C	109.5	N1—C10—H10B	108.2
H3B—C3—H3C	109.5	H10A—C10—H10B	107.4
C5—C4—N1	115.4 (2)	C10—C11—C12	110.5 (2)
C5—C4—H4A	108.4	C10—C11—H11A	109.6
N1—C4—H4A	108.4	C12—C11—H11A	109.6
C5—C4—H4B	108.4	C10—C11—H11B	109.6
N1—C4—H4B	108.4	C12—C11—H11B	109.6
H4A—C4—H4B	107.5	H11A—C11—H11B	108.1
C6—C5—C4	108.7 (3)	C11—C12—H12A	109.5
C6—C5—H5A	110.0	C11—C12—H12B	109.5
C4—C5—H5A	110.0	H12A—C12—H12B	109.5
C6—C5—H5B	110.0	C11—C12—H12C	109.5
C4—C5—H5B	110.0	H12A—C12—H12C	109.5
H5A—C5—H5B	108.3	H12B—C12—H12C	109.5
C5—C6—H6A	109.5	C1—N1—C10	108.64 (18)
C5—C6—H6B	109.5	C1—N1—C4	111.11 (18)
H6A—C6—H6B	109.5	C10—N1—C4	108.60 (18)
C5—C6—H6C	109.5	C1—N1—C7	108.65 (18)
H6A—C6—H6C	109.5	C10—N1—C7	111.38 (17)
H6B—C6—H6C	109.5	C4—N1—C7	108.48 (17)
C8—C7—N1	115.7 (2)	O4—Cl1—O2	110.03 (17)
C8—C7—H7A	108.4	O4—Cl1—O1	111.13 (14)
N1—C7—H7A	108.4	O2—Cl1—O1	110.01 (14)
C8—C7—H7B	108.4	O4—Cl1—O3	109.81 (18)
N1—C7—H7B	108.4	O2—Cl1—O3	106.78 (14)
H7A—C7—H7B	107.4	O1—Cl1—O3	108.97 (15)
N1—C1—C2—C3	171.7 (2)	C11—C10—N1—C4	−61.4 (3)
N1—C4—C5—C6	173.8 (2)	C11—C10—N1—C7	58.0 (3)
N1—C7—C8—C9	179.6 (2)	C5—C4—N1—C1	−49.7 (3)
N1—C10—C11—C12	−177.2 (2)	C5—C4—N1—C10	−169.2 (2)
C2—C1—N1—C10	64.1 (3)	C5—C4—N1—C7	69.6 (3)
C2—C1—N1—C4	−55.3 (3)	C8—C7—N1—C1	−70.1 (3)
C2—C1—N1—C7	−174.6 (2)	C8—C7—N1—C10	49.5 (3)
C11—C10—N1—C1	177.6 (2)	C8—C7—N1—C4	169.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O4	0.99	2.42	3.288 (3)	146
C7—H7B···O2^i	0.99	2.51	3.478 (3)	166
C6—H6C···O1^i	0.98	2.59	3.334 (4)	133
C5—H5B···O4^ii	0.99	2.58	3.423 (4)	143
C4—H4A···O4	0.99	2.60	3.500 (3)	152
C1—H1A···O3^iii	0.99	2.41	3.356 (4)	160

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