n-Propyl gallate–acetonitrile (2/1)

Mizuguchi, J.; Hitachi, A.; Iwata, S.; Makino, T.

doi:10.1107/S1600536805022166

n-Propyl gallate–acetonitrile (2/1)

J. Mizuguchi, A. Hitachi, S. Iwata and T. Makino

n-Propyl gallate (PG) is a charge-control agent used for toners in electrophotography, and shows pseudo-polymorphism. In the asymmetric unit of the title compound, 2C₁₀H₁₂O₅·CH₃CN, there are two PG molecules and one solvent molecule. There are intra- and intermolecular O—H

O hydrogen bonds, forming a three-dimensional hydrogen-bond network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805022166/ob6543sup1.cif Contains datablocks global, III
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805022166/ob6543IIIsup2.hkl Contains datablock III

CCDC reference: 282557

checkCIF report

Key indicators

Single-crystal X-ray study
T = 93 K
Mean (C-C) = 0.002 Å
R factor = 0.047
wR factor = 0.134
Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           68.24
           From the CIF: _diffrn_reflns_theta_full          68.24
           From the CIF: _reflns_number_total               3588
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3978
           Completeness (_total/calc)             90.20%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.90
PLAT028_ALERT_3_C _diffrn_measured_fraction_theta_max  Low .......       0.92
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?

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

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

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

n-Propyl gallate–acetonitrile (2/1) top

Crystal data top

2C₁₀H₁₂O₅·C₂H₃N	Z = 2
M_r = 465.45	F(000) = 492.0
Triclinic, P1	D_x = 1.419 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 8.5884 (11) Å	Cell parameters from 8945 reflections
b = 11.3727 (13) Å	θ = 3.9–68.2°
c = 12.5530 (14) Å	µ = 0.96 mm⁻¹
α = 67.648 (9)°	T = 93 K
β = 74.069 (10)°	Platelet, colourless
γ = 81.488 (11)°	0.10 × 0.10 × 0.10 mm
V = 1089.1 (2) Å³

Data collection top

Rigaku R-AXIS RAPID-F imaging-plate diffractometer	3257 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.045
48 frames, Δ ω = 15° scans	θ_max = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
T_min = 0.898, T_max = 0.909	k = −13→13
9830 measured reflections	l = −14→15
3588 independent reflections

Refinement top

Refinement on F	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.047	w = 1/[σ²(F_o²) + {0.05[max(F_o²,0) + 2F_c²]/3}²]
wR(F²) = 0.134	(Δ/σ)_max = 0.002
S = 1.89	Δρ_max = 0.49 e Å⁻³
3588 reflections	Δρ_min = −0.43 e Å⁻³
310 parameters

Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using reflections with F² > 2.0 σ(F²). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
O1	1.03278 (16)	0.27786 (11)	0.88788 (11)	0.0221 (3)
O2	1.07261 (14)	0.26960 (11)	0.67169 (10)	0.0202 (3)
O3	0.94237 (14)	0.08455 (11)	0.63839 (10)	0.0183 (3)
O4	0.63677 (14)	−0.07433 (11)	1.16470 (10)	0.0195 (3)
O5	0.60447 (14)	−0.15281 (10)	1.03316 (9)	0.0194 (3)
O6	0.75298 (14)	0.04713 (11)	0.27468 (10)	0.0195 (3)
O7	0.82042 (14)	0.04817 (11)	0.47195 (10)	0.0185 (3)
O8	0.61235 (15)	0.14237 (11)	0.62147 (10)	0.0190 (3)
O9	0.12441 (14)	0.31578 (11)	0.43847 (9)	0.0206 (3)
O10	0.18901 (14)	0.26076 (11)	0.27810 (10)	0.0189 (3)
N1	0.2804 (2)	0.46683 (16)	0.67868 (15)	0.0358 (5)
C1	0.9534 (2)	0.19024 (15)	0.87535 (14)	0.0177 (4)
C2	0.9762 (2)	0.18328 (15)	0.76281 (14)	0.0169 (4)
C3	0.9019 (2)	0.09021 (15)	0.75027 (13)	0.0162 (4)
C4	0.8011 (2)	0.00704 (15)	0.84707 (14)	0.0165 (4)
C5	0.8522 (2)	0.10801 (15)	0.97262 (14)	0.0174 (4)
C6	0.7744 (2)	0.01666 (14)	0.95879 (14)	0.0163 (4)
C7	0.6670 (2)	−0.07255 (15)	1.06245 (14)	0.0170 (4)
C8	0.5110 (2)	−0.25611 (15)	1.12727 (14)	0.0188 (4)
C9	0.4877 (2)	−0.34490 (16)	1.06974 (15)	0.0235 (4)
C10	0.3892 (2)	−0.45703 (17)	1.15860 (17)	0.0294 (5)
C11	0.6379 (2)	0.10258 (14)	0.34283 (14)	0.0159 (4)
C12	0.6775 (2)	0.10118 (14)	0.44420 (14)	0.0160 (4)
C13	0.5669 (2)	0.15236 (15)	0.52081 (13)	0.0163 (4)
C14	0.4208 (2)	0.20807 (14)	0.49597 (14)	0.0166 (4)
C15	0.3813 (2)	0.20963 (14)	0.39479 (13)	0.0163 (4)
C16	0.4899 (2)	0.15671 (15)	0.31761 (13)	0.0172 (4)
C17	0.2204 (2)	0.26637 (14)	0.37428 (13)	0.0170 (4)
C18	0.0337 (2)	0.32312 (16)	0.25402 (14)	0.0187 (4)
C19	0.0102 (2)	0.30386 (16)	0.14728 (15)	0.0221 (4)
C20	−0.1442 (2)	0.37793 (17)	0.11433 (15)	0.0243 (4)
C21	0.2711 (2)	0.51374 (17)	0.58191 (17)	0.0251 (4)
C22	0.2552 (2)	0.57029 (18)	0.46067 (17)	0.0314 (5)
H1O	1.087 (2)	0.318 (2)	0.8221 (19)	0.0268*
H2O	1.076 (2)	0.2608 (19)	0.6086 (19)	0.0268*
H3O	0.869 (2)	0.074 (2)	0.6216 (19)	0.0268*
H4	0.7504	−0.0562	0.8379	0.020*
H5	0.8356	0.1134	1.0487	0.021*
H6O	0.713 (2)	0.0154 (19)	0.2354 (18)	0.0268*
H7O	0.876 (2)	0.0087 (19)	0.4248 (18)	0.0268*
H8O	0.529 (2)	0.134 (2)	0.676 (2)	0.0268*
H8a	0.5686	−0.2994	1.1872	0.023*
H8b	0.4090	−0.2238	1.1612	0.023*
H9a	0.5909	−0.3760	1.0363	0.028*
H9b	0.4326	−0.2992	1.0088	0.028*
H10a	0.4427	−0.5027	1.2204	0.035*
H10b	0.2848	−0.4269	1.1911	0.035*
H10c	0.3783	−0.5117	1.1199	0.035*
H14	0.3473	0.2453	0.5476	0.020*
H16	0.4630	0.1577	0.2487	0.021*
H18a	0.0344	0.4116	0.2386	0.022*
H18b	−0.0520	0.2868	0.3207	0.022*
H19a	0.1007	0.3337	0.0825	0.027*
H19b	0.0007	0.2158	0.1652	0.027*
H20a	−0.1350	0.4659	0.0969	0.029*
H20b	−0.2349	0.3477	0.1789	0.029*
H20c	−0.1586	0.3662	0.0467	0.029*
H22a	0.2826	0.6569	0.4290	0.038*
H22b	0.1466	0.5656	0.4587	0.038*
H22c	0.3261	0.5255	0.4146	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0247 (7)	0.0260 (6)	0.0174 (6)	−0.0094 (5)	−0.0008 (5)	−0.0096 (5)
O2	0.0218 (7)	0.0251 (6)	0.0151 (5)	−0.0066 (5)	−0.0014 (5)	−0.0088 (4)
O3	0.0139 (6)	0.0288 (6)	0.0169 (5)	−0.0003 (4)	−0.0040 (5)	−0.0133 (4)
O4	0.0205 (7)	0.0233 (6)	0.0158 (5)	−0.0036 (5)	−0.0029 (5)	−0.0081 (4)
O5	0.0227 (7)	0.0187 (5)	0.0178 (5)	−0.0049 (4)	−0.0042 (5)	−0.0068 (4)
O6	0.0173 (6)	0.0270 (6)	0.0184 (5)	−0.0003 (5)	−0.0028 (5)	−0.0139 (4)
O7	0.0161 (6)	0.0246 (6)	0.0188 (6)	0.0019 (5)	−0.0049 (5)	−0.0127 (5)
O8	0.0176 (7)	0.0273 (6)	0.0150 (5)	−0.0019 (5)	−0.0033 (5)	−0.0110 (4)
O9	0.0189 (7)	0.0237 (6)	0.0182 (5)	0.0009 (5)	−0.0031 (5)	−0.0081 (5)
O10	0.0179 (7)	0.0228 (6)	0.0176 (5)	0.0008 (4)	−0.0064 (5)	−0.0080 (4)
N1	0.0432 (11)	0.0305 (9)	0.0355 (9)	0.0039 (7)	−0.0163 (8)	−0.0110 (7)
C1	0.0173 (9)	0.0178 (7)	0.0213 (8)	0.0017 (6)	−0.0070 (7)	−0.0097 (6)
C2	0.0149 (9)	0.0188 (8)	0.0165 (8)	0.0006 (6)	−0.0033 (7)	−0.0066 (6)
C3	0.0148 (9)	0.0206 (8)	0.0154 (7)	0.0034 (6)	−0.0046 (7)	−0.0098 (6)
C4	0.0146 (9)	0.0175 (8)	0.0202 (8)	0.0009 (6)	−0.0047 (7)	−0.0099 (6)
C5	0.0180 (9)	0.0210 (8)	0.0155 (7)	0.0006 (6)	−0.0053 (7)	−0.0087 (6)
C6	0.0153 (9)	0.0164 (7)	0.0179 (8)	0.0023 (6)	−0.0055 (7)	−0.0068 (6)
C7	0.0141 (9)	0.0192 (8)	0.0202 (8)	0.0031 (6)	−0.0069 (7)	−0.0094 (6)
C8	0.0195 (9)	0.0176 (7)	0.0178 (7)	−0.0023 (6)	−0.0032 (7)	−0.0050 (6)
C9	0.0234 (10)	0.0223 (8)	0.0260 (9)	−0.0036 (7)	−0.0031 (8)	−0.0108 (7)
C10	0.0341 (12)	0.0233 (9)	0.0314 (10)	−0.0079 (8)	−0.0050 (9)	−0.0103 (7)
C11	0.0168 (9)	0.0157 (7)	0.0146 (7)	−0.0051 (6)	0.0005 (7)	−0.0059 (6)
C12	0.0150 (9)	0.0161 (7)	0.0166 (7)	−0.0045 (6)	−0.0029 (7)	−0.0050 (6)
C13	0.0186 (9)	0.0178 (7)	0.0138 (7)	−0.0053 (6)	−0.0041 (7)	−0.0053 (6)
C14	0.0176 (9)	0.0158 (7)	0.0162 (7)	−0.0024 (6)	−0.0014 (7)	−0.0069 (6)
C15	0.0172 (9)	0.0146 (7)	0.0155 (7)	−0.0030 (6)	−0.0033 (7)	−0.0031 (6)
C16	0.0185 (9)	0.0183 (7)	0.0146 (7)	−0.0050 (6)	−0.0035 (7)	−0.0045 (6)
C17	0.0190 (10)	0.0154 (7)	0.0142 (7)	−0.0043 (6)	−0.0013 (7)	−0.0033 (6)
C18	0.0144 (9)	0.0222 (8)	0.0193 (8)	0.0012 (6)	−0.0044 (7)	−0.0076 (6)
C19	0.0224 (10)	0.0237 (8)	0.0220 (8)	0.0015 (7)	−0.0072 (7)	−0.0097 (6)
C20	0.0229 (10)	0.0290 (9)	0.0232 (8)	0.0031 (7)	−0.0087 (8)	−0.0112 (7)
C21	0.0195 (10)	0.0221 (8)	0.0353 (10)	−0.0008 (7)	−0.0050 (8)	−0.0130 (7)
C22	0.0338 (12)	0.0292 (10)	0.0296 (10)	−0.0046 (8)	−0.0075 (9)	−0.0078 (8)

Geometric parameters (Å, º) top

O1—C1	1.365 (2)	C8—H8b	0.950
O1—H1O	0.822 (19)	C9—C10	1.518 (2)
O2—C2	1.3508 (17)	C9—H9a	0.950
O2—H2O	0.83 (2)	C9—H9b	0.950
O3—C3	1.375 (2)	C10—H10a	0.950
O3—H3O	0.75 (2)	C10—H10b	0.950
O4—C7	1.231 (2)	C10—H10c	0.950
O5—C7	1.329 (2)	C11—C12	1.399 (2)
O5—C8	1.4570 (17)	C11—C16	1.391 (2)
O6—C11	1.367 (2)	C12—C13	1.388 (2)
O6—H6O	0.87 (2)	C13—C14	1.379 (2)
O7—C12	1.359 (2)	C14—C15	1.395 (2)
O7—H7O	0.88 (2)	C14—H14	0.950
O8—C13	1.382 (2)	C15—C16	1.397 (2)
O8—H8O	0.84 (2)	C15—C17	1.483 (2)
O9—C17	1.219 (2)	C16—H16	0.950
O10—C17	1.333 (2)	C18—C19	1.506 (3)
O10—C18	1.467 (2)	C18—H18a	0.950
N1—C21	1.147 (2)	C18—H18b	0.950
C1—C2	1.403 (2)	C19—C20	1.531 (2)
C1—C5	1.382 (2)	C19—H19a	0.950
C2—C3	1.391 (2)	C19—H19b	0.950
C3—C4	1.3824 (19)	C20—H20a	0.950
C4—C6	1.401 (2)	C20—H20b	0.950
C4—H4	0.950	C20—H20c	0.950
C5—C6	1.401 (2)	C21—C22	1.446 (2)
C5—H5	0.950	C22—H22a	0.950
C6—C7	1.4790 (19)	C22—H22b	0.950
C8—C9	1.509 (3)	C22—H22c	0.950
C8—H8a	0.950

O1···H20cⁱ	2.631	H5···O6^iv	2.559
O2···O9ⁱⁱ	2.6888 (17)	H5···H6O^iv	2.203
O2···H14ⁱⁱ	2.487	H6O···O4^vi	1.86 (2)
O3···O7	2.761 (2)	H6O···H5^vi	2.203
O3···O7ⁱⁱⁱ	2.7346 (17)	H6O···H8O^x	2.60 (3)
O3···H7Oⁱⁱⁱ	1.91 (2)	H7O···O3ⁱⁱⁱ	1.91 (2)
O4···O6^iv	2.725 (2)	H7O···H3Oⁱⁱⁱ	2.26 (3)
O4···H6O^iv	1.86 (2)	H8O···O4^v	2.04 (2)
O4···H8O^v	2.04 (2)	H8O···H6O^x	2.60 (3)
O6···O4^vi	2.725 (2)	H8O···H22a^vii	2.762
O6···H5^vi	2.559	H8a···N1^v	2.484
O6···H19bⁱⁱ	2.774	H8b···C6^v	2.794
O7···O3	2.761 (2)	H9a···H10c^xi	2.659
O7···O3ⁱⁱⁱ	2.7346 (17)	H9a···H19a^x	2.671
O7···H3O	2.16 (2)	H10a···H22c^xii	2.492
O8···H3O	2.23 (2)	H10b···H22c^xii	2.762
O8···H22a^vii	2.371	H10c···H9a^xi	2.659
O9···O2^viii	2.6888 (17)	H14···O2^viii	2.487
O9···H2O^viii	1.92 (2)	H14···H2O^viii	2.250
O9···H22b^ix	2.765	H19a···H9a^x	2.671
N1···H1O^viii	2.39 (2)	H19a···H20a^xiii	2.507
N1···H8a^v	2.484	H19b···O6^viii	2.774
C6···H8b^v	2.794	H19b···H4^x	2.594
H1O···N1ⁱⁱ	2.39 (2)	H20a···H19a^xiii	2.507
H2O···O9ⁱⁱ	1.92 (2)	H20c···O1^xiv	2.631
H2O···H14ⁱⁱ	2.250	H22a···O8^vii	2.371
H2O···H22b^vii	2.599	H22a···H8O^vii	2.762
H3O···O7	2.16 (2)	H22b···O9^ix	2.765
H3O···O8	2.23 (2)	H22b···H2O^vii	2.599
H3O···H7Oⁱⁱⁱ	2.26 (3)	H22c···H10a^xv	2.492
H4···H19b^x	2.594	H22c···H10b^xv	2.762

C1—O1—H1O	108 (2)	O5—C7—C6	112.11 (15)
C2—O2—H2O	109.8 (14)	O5—C8—C9	106.17 (13)
C3—O3—H3O	111.4 (17)	C8—C9—C10	111.63 (15)
C7—O5—C8	118.77 (13)	O6—C11—C12	115.09 (15)
C11—O6—H6O	113.2 (13)	O6—C11—C16	124.50 (18)
C12—O7—H7O	112.4 (16)	C12—C11—C16	120.41 (16)
C13—O8—H8O	107.8 (19)	O7—C12—C11	121.91 (15)
C17—O10—C18	114.46 (13)	O7—C12—C13	118.56 (17)
O1—C1—C2	119.50 (13)	C11—C12—C13	119.51 (16)
O1—C1—C5	120.49 (17)	O8—C13—C12	115.95 (15)
C2—C1—C5	120.01 (18)	O8—C13—C14	123.38 (15)
O2—C2—C1	116.42 (17)	C12—C13—C14	120.67 (18)
O2—C2—C3	123.76 (16)	C13—C14—C15	119.80 (16)
C1—C2—C3	119.82 (13)	C14—C15—C16	120.38 (16)
O3—C3—C2	115.35 (12)	C14—C15—C17	117.77 (15)
O3—C3—C4	123.96 (18)	C16—C15—C17	121.84 (17)
C2—C3—C4	120.62 (17)	C11—C16—C15	119.20 (18)
C3—C4—C6	119.49 (18)	O9—C17—O10	122.17 (16)
C1—C5—C6	119.83 (17)	O9—C17—C15	123.42 (18)
C4—C6—C5	120.17 (13)	O10—C17—C15	114.40 (14)
C4—C6—C7	119.51 (17)	O10—C18—C19	108.81 (14)
C5—C6—C7	120.29 (16)	C18—C19—C20	109.54 (16)
O4—C7—O5	122.70 (13)	N1—C21—C22	178.2 (2)
O4—C7—C6	125.19 (18)

Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y, z; (iii) −x+2, −y, −z+1; (iv) x, y, z+1; (v) −x+1, −y, −z+2; (vi) x, y, z−1; (vii) −x+1, −y+1, −z+1; (viii) x−1, y, z; (ix) −x, −y+1, −z+1; (x) −x+1, −y, −z+1; (xi) −x+1, −y−1, −z+2; (xii) x, y−1, z+1; (xiii) −x, −y+1, −z; (xiv) x−1, y, z−1; (xv) x, y+1, z−1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2	0.82 (2)	2.20 (2)	2.677 (2)	117 (2)
O1—H1O···N1ⁱⁱ	0.82 (2)	2.39 (2)	3.1675 (19)	158 (2)
O2—H2O···O3	0.83 (2)	2.31 (2)	2.735 (2)	112 (2)
O2—H2O···O9ⁱⁱ	0.83 (2)	1.92 (2)	2.6888 (17)	153 (2)
O3—H3O···O7	0.75 (2)	2.16 (2)	2.761 (2)	137 (2)
O3—H3O···O8	0.75 (2)	2.23 (2)	2.8606 (18)	142 (2)
O6—H6O···O4^vi	0.87 (2)	1.86 (2)	2.725 (2)	172 (2)
O7—H7O···O3ⁱⁱⁱ	0.88 (2)	1.91 (2)	2.7346 (17)	156 (2)
O7—H7O···O6	0.88 (2)	2.28 (2)	2.698 (2)	109 (2)
O8—H8O···O4^v	0.84 (2)	2.04 (2)	2.8528 (15)	164 (2)

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

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