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The cations and anions of the title compound, 2C7H10N+·SO42−, are linked into a layer by N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807007465/hb2294sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807007465/hb2294Isup2.hkl
Contains datablock I

CCDC reference: 640348

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.109
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.35 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6 PLAT731_ALERT_1_C Bond Calc 0.881(11), Rep 0.880(5) ...... 2.20 su-Ra N1 -H1N1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.879(11), Rep 0.880(5) ...... 2.20 su-Ra N1 -H1N2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.879(13), Rep 0.880(5) ...... 2.60 su-Ra N2 -H2N2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.998(12), Rep 0.997(5) ...... 2.40 su-Ra C1 -H1B 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.952(13), Rep 0.952(5) ...... 2.60 su-Ra C3 -H3 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.952(11), Rep 0.952(5) ...... 2.20 su-Ra C4 -H4 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.949(14), Rep 0.950(5) ...... 2.80 su-Ra C5 -H5 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.951(14), Rep 0.951(5) ...... 2.80 su-Ra C6 -H6 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.951(12), Rep 0.950(5) ...... 2.40 su-Ra C7 -H7 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.950(17), Rep 0.951(5) ...... 3.40 su-Ra C10 -H10 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.951(15), Rep 0.952(5) ...... 3.00 su-Ra C11 -H11 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.949(14), Rep 0.949(5) ...... 2.80 su-Ra C12 -H12 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.950(18), Rep 0.951(5) ...... 3.60 su-Ra C13 -H13 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.954(12), Rep 0.953(5) ...... 2.40 su-Ra C14 -H14 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.879(13), Rep 0.88(5) ...... 3.85 su-Ra N2 -H5# 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.952(11), Rep 1.953(5) ...... 2.20 su-Ra H1# -O1 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 21 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 17 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX-II (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

Bis(benzylammonium) sulfate top
Crystal data top
2C7H10N+·SO42F(000) = 1328
Mr = 312.38Dx = 1.372 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 8378 reflections
a = 10.1018 (1) Åθ = 2.4–34.7°
b = 10.1628 (1) ŵ = 0.23 mm1
c = 29.4514 (4) ÅT = 173 K
V = 3023.56 (6) Å3Block, colorless
Z = 80.50 × 0.32 × 0.18 mm
Data collection top
Bruker APEX-II
diffractometer
4029 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 30.0°, θmin = 1.4°
φ and ω scansh = 1414
50784 measured reflectionsk = 1413
4410 independent reflectionsl = 4141
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: difference Fourier map
wR(F2) = 0.109All H-atom parameters refined
S = 1.10 w = 1/[σ2(Fo2) + (0.0691P)2 + 1.1013P]
where P = (Fo2 + 2Fc2)/3
4410 reflections(Δ/σ)max = 0.001
270 parametersΔρmax = 0.52 e Å3
20 restraintsΔρmin = 0.47 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.60797 (2)0.72370 (2)0.529132 (8)0.01095 (9)
O10.61234 (7)0.85058 (7)0.55449 (3)0.01451 (16)
O20.73587 (8)0.65576 (8)0.53435 (3)0.01526 (16)
O30.58246 (9)0.75473 (8)0.48078 (3)0.01863 (17)
O40.50087 (8)0.64071 (8)0.54704 (4)0.0244 (2)
N10.36798 (9)0.97598 (9)0.53597 (3)0.01264 (17)
N20.88731 (9)0.89025 (9)0.56537 (3)0.01294 (17)
C10.26721 (10)0.96019 (11)0.57263 (4)0.01504 (19)
C20.30267 (10)1.03580 (10)0.61489 (3)0.01308 (18)
C30.42145 (11)1.01252 (10)0.63801 (4)0.01511 (19)
C40.45140 (11)1.08332 (11)0.67720 (4)0.0172 (2)
C50.36272 (12)1.17576 (11)0.69412 (4)0.0185 (2)
C60.24442 (12)1.19870 (12)0.67135 (4)0.0202 (2)
C70.21497 (11)1.12968 (11)0.63173 (4)0.0168 (2)
C80.92998 (11)0.81249 (12)0.60580 (4)0.0182 (2)
C90.85373 (11)0.84662 (11)0.64800 (4)0.0164 (2)
C100.73502 (12)0.78196 (12)0.65704 (4)0.0221 (2)
C110.66481 (14)0.80911 (15)0.69659 (5)0.0312 (3)
C120.71253 (17)0.90038 (15)0.72720 (4)0.0348 (3)
C130.83016 (19)0.96467 (14)0.71877 (5)0.0357 (3)
C140.90136 (14)0.93790 (13)0.67909 (4)0.0260 (3)
H1n10.4452 (9)0.9407 (15)0.5427 (5)0.020 (4)*
H1n20.3384 (15)0.9371 (14)0.5113 (3)0.017 (4)*
H1n30.3801 (15)1.0602 (6)0.5308 (5)0.015 (4)*
H2n10.8014 (6)0.8820 (16)0.5611 (6)0.025 (4)*
H2n20.9253 (15)0.8551 (15)0.5414 (4)0.020 (4)*
H2n30.9122 (16)0.9738 (7)0.5665 (6)0.024 (4)*
H1a0.2627 (16)0.8641 (6)0.5795 (6)0.022 (4)*
H1b0.1823 (10)0.9925 (16)0.5594 (6)0.027 (4)*
H30.4810 (13)0.9482 (12)0.6264 (5)0.020 (4)*
H40.5347 (9)1.0694 (16)0.6915 (5)0.023 (4)*
H50.3824 (19)1.2283 (16)0.7199 (4)0.034 (5)*
H60.1841 (14)1.2639 (13)0.6818 (6)0.028 (4)*
H70.1348 (10)1.1443 (17)0.6156 (5)0.026 (4)*
H8a1.0268 (6)0.8302 (17)0.6089 (6)0.027 (4)*
H8b0.9174 (18)0.7174 (7)0.5986 (6)0.031 (5)*
H100.7005 (19)0.7157 (15)0.6376 (6)0.038 (5)*
H110.5843 (12)0.7650 (19)0.7036 (8)0.050 (6)*
H120.6675 (19)0.917 (2)0.7549 (4)0.042 (5)*
H130.865 (2)1.0244 (17)0.7405 (6)0.047 (6)*
H140.9852 (10)0.9780 (18)0.6736 (6)0.039 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01046 (13)0.00945 (13)0.01295 (14)0.00040 (7)0.00051 (7)0.00045 (7)
O10.0155 (3)0.0128 (3)0.0153 (3)0.0031 (2)0.0015 (3)0.0040 (3)
O20.0138 (3)0.0154 (3)0.0166 (3)0.0047 (3)0.0008 (3)0.0020 (3)
O30.0271 (4)0.0149 (3)0.0140 (4)0.0011 (3)0.0072 (3)0.0004 (3)
O40.0165 (4)0.0150 (4)0.0416 (5)0.0020 (3)0.0106 (4)0.0048 (3)
N10.0141 (4)0.0120 (4)0.0117 (4)0.0012 (3)0.0006 (3)0.0011 (3)
N20.0137 (4)0.0120 (4)0.0131 (4)0.0005 (3)0.0006 (3)0.0006 (3)
C10.0132 (4)0.0171 (4)0.0148 (4)0.0023 (3)0.0010 (3)0.0019 (3)
C20.0137 (4)0.0132 (4)0.0124 (4)0.0015 (3)0.0014 (3)0.0009 (3)
C30.0151 (4)0.0156 (4)0.0146 (4)0.0009 (4)0.0008 (4)0.0007 (3)
C40.0186 (5)0.0179 (5)0.0150 (4)0.0001 (4)0.0021 (4)0.0016 (4)
C50.0237 (5)0.0185 (5)0.0132 (4)0.0005 (4)0.0000 (4)0.0015 (4)
C60.0221 (5)0.0202 (5)0.0184 (5)0.0045 (4)0.0018 (4)0.0036 (4)
C70.0151 (5)0.0178 (5)0.0176 (5)0.0024 (4)0.0003 (4)0.0004 (4)
C80.0175 (5)0.0217 (5)0.0155 (5)0.0070 (4)0.0018 (4)0.0044 (4)
C90.0180 (5)0.0177 (4)0.0135 (4)0.0052 (4)0.0000 (4)0.0028 (3)
C100.0199 (5)0.0257 (6)0.0206 (5)0.0027 (4)0.0012 (4)0.0051 (4)
C110.0273 (6)0.0381 (7)0.0281 (6)0.0120 (6)0.0116 (5)0.0154 (5)
C120.0521 (9)0.0348 (7)0.0175 (5)0.0260 (6)0.0114 (5)0.0098 (5)
C130.0623 (10)0.0265 (6)0.0185 (6)0.0139 (6)0.0044 (6)0.0040 (5)
C140.0350 (7)0.0214 (6)0.0217 (6)0.0004 (5)0.0040 (5)0.0005 (4)
Geometric parameters (Å, º) top
S1—O41.4698 (8)C4—H40.952 (5)
S1—O21.4730 (8)C5—C61.3901 (17)
S1—O31.4812 (8)C5—H50.950 (5)
S1—O11.4908 (8)C6—C71.3936 (15)
N1—C11.4926 (14)C6—H60.951 (5)
N1—H1n10.880 (5)C7—H70.950 (5)
N1—H1n20.880 (5)C8—C91.5028 (15)
N1—H1n30.878 (5)C8—H8a0.998 (5)
N2—C81.4927 (14)C8—H8b0.998 (5)
N2—H2n10.881 (5)C9—C141.3894 (17)
N2—H2n20.880 (5)C9—C101.3931 (17)
N2—H2n30.886 (5)C10—C111.3911 (18)
C1—C21.5058 (14)C10—H100.951 (5)
C1—H1a0.998 (5)C11—C121.381 (2)
C1—H1b0.997 (5)C11—H110.952 (5)
C2—C71.3932 (14)C12—C131.379 (3)
C2—C31.3999 (15)C12—H120.949 (5)
C3—C41.3933 (15)C13—C141.399 (2)
C3—H30.952 (5)C13—H130.951 (5)
C4—C51.3904 (16)C14—H140.953 (5)
O4—S1—O2109.83 (5)C6—C5—C4119.62 (10)
O4—S1—O3109.82 (6)C6—C5—H5118.2 (12)
O2—S1—O3110.65 (5)C4—C5—H5122.1 (12)
O4—S1—O1109.78 (5)C5—C6—C7120.21 (10)
O2—S1—O1109.10 (4)C5—C6—H6120.8 (11)
O3—S1—O1107.62 (5)C7—C6—H6119.0 (11)
C1—N1—H1n1113.4 (11)C2—C7—C6120.46 (10)
C1—N1—H1n2108.6 (11)C2—C7—H7118.1 (11)
H1n1—N1—H1n2107.7 (15)C6—C7—H7121.4 (11)
C1—N1—H1n3109.0 (10)N2—C8—C9112.92 (9)
H1n1—N1—H1n3108.2 (15)N2—C8—H8a105.1 (10)
H1n2—N1—H1n3109.9 (14)C9—C8—H8a112.7 (10)
C8—N2—H2n1110.3 (11)N2—C8—H8b107.9 (11)
C8—N2—H2n2107.4 (11)C9—C8—H8b109.5 (11)
H2n1—N2—H2n2106.1 (15)H8a—C8—H8b108.5 (15)
C8—N2—H2n3113.2 (11)C14—C9—C10119.14 (11)
H2n1—N2—H2n3112.1 (15)C14—C9—C8121.44 (11)
H2n2—N2—H2n3107.2 (15)C10—C9—C8119.37 (11)
N1—C1—C2112.38 (8)C11—C10—C9120.36 (13)
N1—C1—H1a106.4 (10)C11—C10—H10117.3 (13)
C2—C1—H1a110.0 (10)C9—C10—H10122.3 (13)
N1—C1—H1b105.6 (10)C12—C11—C10120.13 (14)
C2—C1—H1b111.0 (10)C12—C11—H11118.2 (14)
H1a—C1—H1b111.2 (14)C10—C11—H11121.6 (14)
C7—C2—C3119.18 (10)C13—C12—C11120.11 (12)
C7—C2—C1119.50 (9)C13—C12—H12118.9 (13)
C3—C2—C1121.31 (9)C11—C12—H12120.9 (13)
C4—C3—C2120.12 (10)C12—C13—C14120.10 (14)
C4—C3—H3121.0 (10)C12—C13—H13120.2 (14)
C2—C3—H3118.9 (10)C14—C13—H13119.6 (14)
C5—C4—C3120.39 (10)C9—C14—C13120.16 (14)
C5—C4—H4120.7 (10)C9—C14—H14118.8 (12)
C3—C4—H4118.8 (10)C13—C14—H14120.9 (12)
N1—C1—C2—C7122.30 (10)N2—C8—C9—C1495.04 (13)
N1—C1—C2—C358.54 (13)N2—C8—C9—C1087.34 (13)
C7—C2—C3—C40.42 (15)C14—C9—C10—C110.37 (17)
C1—C2—C3—C4179.59 (10)C8—C9—C10—C11178.05 (11)
C2—C3—C4—C51.19 (16)C9—C10—C11—C120.08 (19)
C3—C4—C5—C60.90 (17)C10—C11—C12—C130.2 (2)
C4—C5—C6—C70.15 (18)C11—C12—C13—C140.2 (2)
C3—C2—C7—C60.62 (16)C10—C9—C14—C130.38 (18)
C1—C2—C7—C6178.55 (10)C8—C9—C14—C13178.01 (11)
C5—C6—C7—C20.92 (17)C12—C13—C14—C90.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n1···O10.88 (1)1.95 (1)2.831 (1)175 (2)
N1—H1n2···O2i0.88 (1)1.94 (1)2.804 (1)166 (2)
N1—H1n3···O3ii0.88 (1)1.95 (1)2.826 (1)177 (2)
N2—H2n1···O10.88 (1)1.95 (1)2.825 (1)175 (2)
N2—H2n2···O3iii0.88 (5)2.05 (1)2.811 (1)145 (2)
N2—H2n3···O4iv0.89 (1)1.99 (1)2.837 (1)158 (2)
Symmetry codes: (i) x1/2, y+3/2, z+1; (ii) x+1, y+2, z+1; (iii) x+1/2, y+3/2, z+1; (iv) x+3/2, y+1/2, z.
 

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