organic compounds
The cations and anions of the title compound, 2C7H10N+·SO42−, are linked into a layer by N—HO hydrogen bonds.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807007465/hb2294sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807007465/hb2294Isup2.hkl |
CCDC reference: 640348
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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+·SO42− | F(000) = 1328 |
Mr = 312.38 | Dx = 1.372 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 8378 reflections |
a = 10.1018 (1) Å | θ = 2.4–34.7° |
b = 10.1628 (1) Å | µ = 0.23 mm−1 |
c = 29.4514 (4) Å | T = 173 K |
V = 3023.56 (6) Å3 | Block, colorless |
Z = 8 | 0.50 × 0.32 × 0.18 mm |
Data collection top
Bruker APEX-II diffractometer | 4029 reflections with I > 2σ(I) |
Radiation source: medium-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 30.0°, θmin = 1.4° |
φ and ω scans | h = −14→14 |
50784 measured reflections | k = −14→13 |
4410 independent reflections | l = −41→41 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.109 | All 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 parameters | Δρmax = 0.52 e Å−3 |
20 restraints | Δρmin = −0.47 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.60797 (2) | 0.72370 (2) | 0.529132 (8) | 0.01095 (9) | |
O1 | 0.61234 (7) | 0.85058 (7) | 0.55449 (3) | 0.01451 (16) | |
O2 | 0.73587 (8) | 0.65576 (8) | 0.53435 (3) | 0.01526 (16) | |
O3 | 0.58246 (9) | 0.75473 (8) | 0.48078 (3) | 0.01863 (17) | |
O4 | 0.50087 (8) | 0.64071 (8) | 0.54704 (4) | 0.0244 (2) | |
N1 | 0.36798 (9) | 0.97598 (9) | 0.53597 (3) | 0.01264 (17) | |
N2 | 0.88731 (9) | 0.89025 (9) | 0.56537 (3) | 0.01294 (17) | |
C1 | 0.26721 (10) | 0.96019 (11) | 0.57263 (4) | 0.01504 (19) | |
C2 | 0.30267 (10) | 1.03580 (10) | 0.61489 (3) | 0.01308 (18) | |
C3 | 0.42145 (11) | 1.01252 (10) | 0.63801 (4) | 0.01511 (19) | |
C4 | 0.45140 (11) | 1.08332 (11) | 0.67720 (4) | 0.0172 (2) | |
C5 | 0.36272 (12) | 1.17576 (11) | 0.69412 (4) | 0.0185 (2) | |
C6 | 0.24442 (12) | 1.19870 (12) | 0.67135 (4) | 0.0202 (2) | |
C7 | 0.21497 (11) | 1.12968 (11) | 0.63173 (4) | 0.0168 (2) | |
C8 | 0.92998 (11) | 0.81249 (12) | 0.60580 (4) | 0.0182 (2) | |
C9 | 0.85373 (11) | 0.84662 (11) | 0.64800 (4) | 0.0164 (2) | |
C10 | 0.73502 (12) | 0.78196 (12) | 0.65704 (4) | 0.0221 (2) | |
C11 | 0.66481 (14) | 0.80911 (15) | 0.69659 (5) | 0.0312 (3) | |
C12 | 0.71253 (17) | 0.90038 (15) | 0.72720 (4) | 0.0348 (3) | |
C13 | 0.83016 (19) | 0.96467 (14) | 0.71877 (5) | 0.0357 (3) | |
C14 | 0.90136 (14) | 0.93790 (13) | 0.67909 (4) | 0.0260 (3) | |
H1n1 | 0.4452 (9) | 0.9407 (15) | 0.5427 (5) | 0.020 (4)* | |
H1n2 | 0.3384 (15) | 0.9371 (14) | 0.5113 (3) | 0.017 (4)* | |
H1n3 | 0.3801 (15) | 1.0602 (6) | 0.5308 (5) | 0.015 (4)* | |
H2n1 | 0.8014 (6) | 0.8820 (16) | 0.5611 (6) | 0.025 (4)* | |
H2n2 | 0.9253 (15) | 0.8551 (15) | 0.5414 (4) | 0.020 (4)* | |
H2n3 | 0.9122 (16) | 0.9738 (7) | 0.5665 (6) | 0.024 (4)* | |
H1a | 0.2627 (16) | 0.8641 (6) | 0.5795 (6) | 0.022 (4)* | |
H1b | 0.1823 (10) | 0.9925 (16) | 0.5594 (6) | 0.027 (4)* | |
H3 | 0.4810 (13) | 0.9482 (12) | 0.6264 (5) | 0.020 (4)* | |
H4 | 0.5347 (9) | 1.0694 (16) | 0.6915 (5) | 0.023 (4)* | |
H5 | 0.3824 (19) | 1.2283 (16) | 0.7199 (4) | 0.034 (5)* | |
H6 | 0.1841 (14) | 1.2639 (13) | 0.6818 (6) | 0.028 (4)* | |
H7 | 0.1348 (10) | 1.1443 (17) | 0.6156 (5) | 0.026 (4)* | |
H8a | 1.0268 (6) | 0.8302 (17) | 0.6089 (6) | 0.027 (4)* | |
H8b | 0.9174 (18) | 0.7174 (7) | 0.5986 (6) | 0.031 (5)* | |
H10 | 0.7005 (19) | 0.7157 (15) | 0.6376 (6) | 0.038 (5)* | |
H11 | 0.5843 (12) | 0.7650 (19) | 0.7036 (8) | 0.050 (6)* | |
H12 | 0.6675 (19) | 0.917 (2) | 0.7549 (4) | 0.042 (5)* | |
H13 | 0.865 (2) | 1.0244 (17) | 0.7405 (6) | 0.047 (6)* | |
H14 | 0.9852 (10) | 0.9780 (18) | 0.6736 (6) | 0.039 (5)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01046 (13) | 0.00945 (13) | 0.01295 (14) | 0.00040 (7) | 0.00051 (7) | 0.00045 (7) |
O1 | 0.0155 (3) | 0.0128 (3) | 0.0153 (3) | 0.0031 (2) | −0.0015 (3) | −0.0040 (3) |
O2 | 0.0138 (3) | 0.0154 (3) | 0.0166 (3) | 0.0047 (3) | −0.0008 (3) | −0.0020 (3) |
O3 | 0.0271 (4) | 0.0149 (3) | 0.0140 (4) | 0.0011 (3) | −0.0072 (3) | −0.0004 (3) |
O4 | 0.0165 (4) | 0.0150 (4) | 0.0416 (5) | −0.0020 (3) | 0.0106 (4) | 0.0048 (3) |
N1 | 0.0141 (4) | 0.0120 (4) | 0.0117 (4) | 0.0012 (3) | −0.0006 (3) | −0.0011 (3) |
N2 | 0.0137 (4) | 0.0120 (4) | 0.0131 (4) | 0.0005 (3) | 0.0006 (3) | 0.0006 (3) |
C1 | 0.0132 (4) | 0.0171 (4) | 0.0148 (4) | −0.0023 (3) | 0.0010 (3) | −0.0019 (3) |
C2 | 0.0137 (4) | 0.0132 (4) | 0.0124 (4) | −0.0015 (3) | 0.0014 (3) | 0.0009 (3) |
C3 | 0.0151 (4) | 0.0156 (4) | 0.0146 (4) | 0.0009 (4) | 0.0008 (4) | 0.0007 (3) |
C4 | 0.0186 (5) | 0.0179 (5) | 0.0150 (4) | 0.0001 (4) | −0.0021 (4) | 0.0016 (4) |
C5 | 0.0237 (5) | 0.0185 (5) | 0.0132 (4) | −0.0005 (4) | 0.0000 (4) | −0.0015 (4) |
C6 | 0.0221 (5) | 0.0202 (5) | 0.0184 (5) | 0.0045 (4) | 0.0018 (4) | −0.0036 (4) |
C7 | 0.0151 (5) | 0.0178 (5) | 0.0176 (5) | 0.0024 (4) | 0.0003 (4) | −0.0004 (4) |
C8 | 0.0175 (5) | 0.0217 (5) | 0.0155 (5) | 0.0070 (4) | 0.0018 (4) | 0.0044 (4) |
C9 | 0.0180 (5) | 0.0177 (4) | 0.0135 (4) | 0.0052 (4) | 0.0000 (4) | 0.0028 (3) |
C10 | 0.0199 (5) | 0.0257 (6) | 0.0206 (5) | 0.0027 (4) | 0.0012 (4) | 0.0051 (4) |
C11 | 0.0273 (6) | 0.0381 (7) | 0.0281 (6) | 0.0120 (6) | 0.0116 (5) | 0.0154 (5) |
C12 | 0.0521 (9) | 0.0348 (7) | 0.0175 (5) | 0.0260 (6) | 0.0114 (5) | 0.0098 (5) |
C13 | 0.0623 (10) | 0.0265 (6) | 0.0185 (6) | 0.0139 (6) | −0.0044 (6) | −0.0040 (5) |
C14 | 0.0350 (7) | 0.0214 (6) | 0.0217 (6) | 0.0004 (5) | −0.0040 (5) | −0.0005 (4) |
Geometric parameters (Å, º) top
S1—O4 | 1.4698 (8) | C4—H4 | 0.952 (5) |
S1—O2 | 1.4730 (8) | C5—C6 | 1.3901 (17) |
S1—O3 | 1.4812 (8) | C5—H5 | 0.950 (5) |
S1—O1 | 1.4908 (8) | C6—C7 | 1.3936 (15) |
N1—C1 | 1.4926 (14) | C6—H6 | 0.951 (5) |
N1—H1n1 | 0.880 (5) | C7—H7 | 0.950 (5) |
N1—H1n2 | 0.880 (5) | C8—C9 | 1.5028 (15) |
N1—H1n3 | 0.878 (5) | C8—H8a | 0.998 (5) |
N2—C8 | 1.4927 (14) | C8—H8b | 0.998 (5) |
N2—H2n1 | 0.881 (5) | C9—C14 | 1.3894 (17) |
N2—H2n2 | 0.880 (5) | C9—C10 | 1.3931 (17) |
N2—H2n3 | 0.886 (5) | C10—C11 | 1.3911 (18) |
C1—C2 | 1.5058 (14) | C10—H10 | 0.951 (5) |
C1—H1a | 0.998 (5) | C11—C12 | 1.381 (2) |
C1—H1b | 0.997 (5) | C11—H11 | 0.952 (5) |
C2—C7 | 1.3932 (14) | C12—C13 | 1.379 (3) |
C2—C3 | 1.3999 (15) | C12—H12 | 0.949 (5) |
C3—C4 | 1.3933 (15) | C13—C14 | 1.399 (2) |
C3—H3 | 0.952 (5) | C13—H13 | 0.951 (5) |
C4—C5 | 1.3904 (16) | C14—H14 | 0.953 (5) |
O4—S1—O2 | 109.83 (5) | C6—C5—C4 | 119.62 (10) |
O4—S1—O3 | 109.82 (6) | C6—C5—H5 | 118.2 (12) |
O2—S1—O3 | 110.65 (5) | C4—C5—H5 | 122.1 (12) |
O4—S1—O1 | 109.78 (5) | C5—C6—C7 | 120.21 (10) |
O2—S1—O1 | 109.10 (4) | C5—C6—H6 | 120.8 (11) |
O3—S1—O1 | 107.62 (5) | C7—C6—H6 | 119.0 (11) |
C1—N1—H1n1 | 113.4 (11) | C2—C7—C6 | 120.46 (10) |
C1—N1—H1n2 | 108.6 (11) | C2—C7—H7 | 118.1 (11) |
H1n1—N1—H1n2 | 107.7 (15) | C6—C7—H7 | 121.4 (11) |
C1—N1—H1n3 | 109.0 (10) | N2—C8—C9 | 112.92 (9) |
H1n1—N1—H1n3 | 108.2 (15) | N2—C8—H8a | 105.1 (10) |
H1n2—N1—H1n3 | 109.9 (14) | C9—C8—H8a | 112.7 (10) |
C8—N2—H2n1 | 110.3 (11) | N2—C8—H8b | 107.9 (11) |
C8—N2—H2n2 | 107.4 (11) | C9—C8—H8b | 109.5 (11) |
H2n1—N2—H2n2 | 106.1 (15) | H8a—C8—H8b | 108.5 (15) |
C8—N2—H2n3 | 113.2 (11) | C14—C9—C10 | 119.14 (11) |
H2n1—N2—H2n3 | 112.1 (15) | C14—C9—C8 | 121.44 (11) |
H2n2—N2—H2n3 | 107.2 (15) | C10—C9—C8 | 119.37 (11) |
N1—C1—C2 | 112.38 (8) | C11—C10—C9 | 120.36 (13) |
N1—C1—H1a | 106.4 (10) | C11—C10—H10 | 117.3 (13) |
C2—C1—H1a | 110.0 (10) | C9—C10—H10 | 122.3 (13) |
N1—C1—H1b | 105.6 (10) | C12—C11—C10 | 120.13 (14) |
C2—C1—H1b | 111.0 (10) | C12—C11—H11 | 118.2 (14) |
H1a—C1—H1b | 111.2 (14) | C10—C11—H11 | 121.6 (14) |
C7—C2—C3 | 119.18 (10) | C13—C12—C11 | 120.11 (12) |
C7—C2—C1 | 119.50 (9) | C13—C12—H12 | 118.9 (13) |
C3—C2—C1 | 121.31 (9) | C11—C12—H12 | 120.9 (13) |
C4—C3—C2 | 120.12 (10) | C12—C13—C14 | 120.10 (14) |
C4—C3—H3 | 121.0 (10) | C12—C13—H13 | 120.2 (14) |
C2—C3—H3 | 118.9 (10) | C14—C13—H13 | 119.6 (14) |
C5—C4—C3 | 120.39 (10) | C9—C14—C13 | 120.16 (14) |
C5—C4—H4 | 120.7 (10) | C9—C14—H14 | 118.8 (12) |
C3—C4—H4 | 118.8 (10) | C13—C14—H14 | 120.9 (12) |
N1—C1—C2—C7 | 122.30 (10) | N2—C8—C9—C14 | −95.04 (13) |
N1—C1—C2—C3 | −58.54 (13) | N2—C8—C9—C10 | 87.34 (13) |
C7—C2—C3—C4 | −0.42 (15) | C14—C9—C10—C11 | 0.37 (17) |
C1—C2—C3—C4 | −179.59 (10) | C8—C9—C10—C11 | 178.05 (11) |
C2—C3—C4—C5 | 1.19 (16) | C9—C10—C11—C12 | −0.08 (19) |
C3—C4—C5—C6 | −0.90 (17) | C10—C11—C12—C13 | −0.2 (2) |
C4—C5—C6—C7 | −0.15 (18) | C11—C12—C13—C14 | 0.2 (2) |
C3—C2—C7—C6 | −0.62 (16) | C10—C9—C14—C13 | −0.38 (18) |
C1—C2—C7—C6 | 178.55 (10) | C8—C9—C14—C13 | −178.01 (11) |
C5—C6—C7—C2 | 0.92 (17) | C12—C13—C14—C9 | 0.1 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n1···O1 | 0.88 (1) | 1.95 (1) | 2.831 (1) | 175 (2) |
N1—H1n2···O2i | 0.88 (1) | 1.94 (1) | 2.804 (1) | 166 (2) |
N1—H1n3···O3ii | 0.88 (1) | 1.95 (1) | 2.826 (1) | 177 (2) |
N2—H2n1···O1 | 0.88 (1) | 1.95 (1) | 2.825 (1) | 175 (2) |
N2—H2n2···O3iii | 0.88 (5) | 2.05 (1) | 2.811 (1) | 145 (2) |
N2—H2n3···O4iv | 0.89 (1) | 1.99 (1) | 2.837 (1) | 158 (2) |
Symmetry codes: (i) x−1/2, −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. |