Crystal structure of di­benzyl­ammonium hydrogen (4-amino­phen­yl)arsonate monohydrate

The title salt consists of three components, comprising one di­benzyl­ammonium cation, [(C₆H₅CH₂)₂NH₂]⁺, one hydrogen (4-amino­phen­yl)arsonate anion, [H₂NC₆H₄As(OH)O₂]⁻, and one mol­ecule of water. In the crystal, these components are organized in infinite zigzag chains via inter­molecular hydrogen bonds. Weak inter­actions between the chains lead to a three-dimensional network.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in solvent or counterion
• R factor = 0.022
• wR factor = 0.054
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check

Author Response: Due to the low multiplicity of the minor water component, the hydrogen atoms were not located and therefore were not included in the model.

PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.01 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          8 Report

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C20 H25 As1 N2 O4
            Atom count from the _atom_site data:  C20 H24.88 As1 N2 O4
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: check formula stoichiometry or atom site occupancies.
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C20 H25 As N2 O4
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         80.00     80.00    0.00
           H        100.00     99.52    0.48
           As         4.00      4.00    0.00
           N          8.00      8.00    0.00
           O         16.00     16.00    0.00
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT300_ALERT_4_G Atom Site Occupancy of O4         Constrained at       0.94 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H4A        Constrained at       0.94 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H4B        Constrained at       0.94 Check
PLAT300_ALERT_4_G Atom Site Occupancy of O4B        Constrained at       0.06 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  4  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  3  )       2.82 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  4  )       0.06 Check
PLAT311_ALERT_2_G Isolated Disordered Oxygen Atom (No H's ?) .....        O4B Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O4B      ..C20      .       3.01 Ang.
                                                      x,y,z  =      1_555 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O4B      ..C13      .       3.01 Ang.
                                                1-x,1-y,1-z  =      3_666 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          5 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          8 Note
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         14 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  20 ALERT level G = General information/check it is not something unexpected

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
   9 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 V8.34A (Bruker, 2014); cell refinement: SAINT V8.34A (Bruker, 2013); data reduction: SAINT V8.34A (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: Olex2 1.5 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009).

Dibenzylammonium hydrogen (4-aminophenyl)arsonate monohydrate

Crystal data

C14H16N^+·C6H7AsNO3^−·H2O	F(000) = 896
Mr = 432.34	Dx = 1.438 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8242 (5) Å	Cell parameters from 9824 reflections
b = 10.6574 (6) Å	θ = 2.8–27.5°
c = 19.2507 (11) Å	µ = 1.73 mm^−1
β = 97.7500 (18)°	T = 100 K
V = 1997.15 (19) Å^3	Prism, clear light colourless
Z = 4	0.5 × 0.25 × 0.18 mm

Data collection

Bruker D8 VENTURE diffractometer	4584 independent reflections
Radiation source: X-ray tube, Siemens KFF Mo 2K-90C	4119 reflections with I > 2σ(I)
TRIUMPH curved crystal monochromator	Rint = 0.037
Detector resolution: 1024 x 1024 pixels mm^-1	θmax = 27.5°, θmin = 2.8°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −13→13
Tmin = 0.610, Tmax = 0.746	l = −24→25
67932 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.022	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.054	w = 1/[σ^2(Fo^2) + (0.0228P)^2 + 1.3431P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
4584 reflections	Δρmax = 0.42 e Å^−3
261 parameters	Δρmin = −0.21 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
As	0.15165 (2)	0.51188 (2)	0.42563 (2)	0.01186 (5)
O1	0.04372 (11)	0.38487 (9)	0.42927 (6)	0.0184 (2)
O2	0.09995 (10)	0.63317 (9)	0.47065 (5)	0.0167 (2)
O3	0.31128 (10)	0.46779 (10)	0.45696 (5)	0.0176 (2)
N2	0.08041 (14)	0.62660 (14)	0.11336 (7)	0.0208 (3)
H2A	0.062 (2)	0.565 (2)	0.0867 (10)	0.025*
H2B	0.043 (2)	0.694 (2)	0.1009 (10)	0.025*
C1	0.13469 (13)	0.55046 (13)	0.32872 (7)	0.0126 (3)
C2	0.13667 (14)	0.45347 (13)	0.27999 (7)	0.0152 (3)
H2	0.149937	0.369445	0.295952	0.018*
C3	0.11956 (15)	0.47831 (14)	0.20880 (7)	0.0164 (3)
H3	0.121018	0.411363	0.176326	0.020*
C4	0.10001 (14)	0.60216 (14)	0.18428 (7)	0.0150 (3)
C5	0.10337 (14)	0.69966 (13)	0.23332 (8)	0.0166 (3)
H5	0.094757	0.784146	0.217604	0.020*
C6	0.11920 (14)	0.67391 (13)	0.30476 (7)	0.0150 (3)
H6	0.119468	0.740721	0.337450	0.018*
O4	0.94231 (17)	0.85325 (13)	0.45149 (7)	0.0389 (3)	0.94
H4A	0.999317	0.790435	0.455138	0.058*	0.94
H4B	0.870836	0.825432	0.468917	0.058*	0.94
N1	0.43532 (12)	0.63057 (11)	0.55144 (6)	0.0142 (2)
H1A	0.391629	0.570678	0.522995	0.017*
H1B	0.523283	0.604491	0.564385	0.017*
C7	0.36565 (15)	0.64208 (13)	0.61550 (7)	0.0156 (3)
H7A	0.268703	0.667011	0.601690	0.019*
H7B	0.411155	0.708549	0.646221	0.019*
C8	0.37054 (14)	0.52036 (13)	0.65533 (7)	0.0134 (3)
C9	0.49603 (15)	0.46656 (14)	0.68231 (8)	0.0167 (3)
H9	0.579319	0.506225	0.674660	0.020*
C10	0.50021 (15)	0.35571 (14)	0.72019 (8)	0.0194 (3)
H10	0.586162	0.319539	0.738161	0.023*
C11	0.37894 (16)	0.29743 (15)	0.73190 (8)	0.0227 (3)
H11	0.381734	0.221469	0.757878	0.027*
C12	0.25392 (16)	0.35050 (15)	0.70557 (9)	0.0251 (3)
H12	0.170863	0.311054	0.713808	0.030*
C13	0.24933 (15)	0.46135 (15)	0.66711 (8)	0.0200 (3)
H13	0.163208	0.496855	0.648829	0.024*
C14	0.43754 (16)	0.75047 (14)	0.51084 (8)	0.0194 (3)
H14A	0.342130	0.775473	0.493084	0.023*
H14B	0.486851	0.736507	0.469927	0.023*
C15	0.50659 (15)	0.85489 (14)	0.55510 (8)	0.0182 (3)
C16	0.42794 (16)	0.94873 (15)	0.57986 (8)	0.0220 (3)
H16	0.330863	0.947490	0.568182	0.026*
C17	0.49027 (19)	1.04468 (15)	0.62169 (9)	0.0277 (4)
H17	0.435865	1.108628	0.638562	0.033*
C18	0.6313 (2)	1.04676 (17)	0.63861 (9)	0.0322 (4)
H18	0.673979	1.112232	0.667157	0.039*
C19	0.71081 (18)	0.95354 (18)	0.61403 (10)	0.0323 (4)
H19	0.807876	0.955423	0.625699	0.039*
C20	0.64919 (16)	0.85748 (16)	0.57247 (9)	0.0249 (3)
H20	0.703946	0.793541	0.555854	0.030*
H1	0.002 (3)	0.386 (3)	0.4638 (14)	0.062 (8)*
O4B	0.729 (2)	0.7346 (18)	0.4434 (10)	0.026 (4)*	0.06

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
As	0.01149 (7)	0.01330 (7)	0.01092 (7)	−0.00011 (5)	0.00195 (5)	−0.00127 (5)
O1	0.0235 (5)	0.0140 (5)	0.0192 (5)	−0.0066 (4)	0.0084 (4)	−0.0043 (4)
O2	0.0200 (5)	0.0125 (5)	0.0187 (5)	−0.0005 (4)	0.0070 (4)	−0.0030 (4)
O3	0.0143 (5)	0.0226 (5)	0.0150 (5)	0.0041 (4)	−0.0009 (4)	−0.0025 (4)
N2	0.0233 (7)	0.0235 (7)	0.0151 (6)	0.0019 (6)	0.0010 (5)	0.0037 (5)
C1	0.0096 (6)	0.0163 (6)	0.0119 (6)	−0.0005 (5)	0.0018 (5)	0.0004 (5)
C2	0.0157 (7)	0.0132 (6)	0.0164 (7)	0.0004 (5)	0.0011 (5)	0.0009 (5)
C3	0.0179 (7)	0.0164 (7)	0.0147 (7)	0.0000 (5)	0.0013 (5)	−0.0022 (5)
C4	0.0097 (6)	0.0198 (7)	0.0158 (7)	0.0003 (5)	0.0026 (5)	0.0029 (5)
C5	0.0149 (7)	0.0140 (6)	0.0211 (7)	0.0016 (5)	0.0035 (5)	0.0042 (5)
C6	0.0127 (6)	0.0147 (6)	0.0179 (7)	−0.0005 (5)	0.0035 (5)	−0.0018 (5)
O4	0.0569 (10)	0.0308 (7)	0.0304 (7)	0.0169 (7)	0.0104 (7)	0.0108 (6)
N1	0.0149 (6)	0.0140 (6)	0.0132 (6)	−0.0003 (4)	0.0007 (4)	0.0000 (4)
C7	0.0170 (7)	0.0144 (6)	0.0160 (7)	0.0009 (5)	0.0045 (5)	−0.0008 (5)
C8	0.0143 (6)	0.0137 (6)	0.0123 (6)	−0.0003 (5)	0.0023 (5)	−0.0020 (5)
C9	0.0129 (6)	0.0194 (7)	0.0181 (7)	−0.0015 (5)	0.0031 (5)	0.0003 (6)
C10	0.0160 (7)	0.0223 (7)	0.0198 (7)	0.0047 (6)	0.0016 (6)	0.0031 (6)
C11	0.0253 (8)	0.0182 (7)	0.0247 (8)	0.0005 (6)	0.0043 (6)	0.0059 (6)
C12	0.0172 (7)	0.0229 (8)	0.0354 (9)	−0.0053 (6)	0.0044 (7)	0.0068 (7)
C13	0.0119 (7)	0.0214 (7)	0.0260 (8)	−0.0005 (5)	−0.0001 (6)	0.0028 (6)
C14	0.0230 (8)	0.0187 (7)	0.0161 (7)	−0.0018 (6)	0.0010 (6)	0.0048 (6)
C15	0.0204 (7)	0.0173 (7)	0.0169 (7)	−0.0042 (6)	0.0022 (6)	0.0057 (6)
C16	0.0226 (8)	0.0191 (7)	0.0246 (8)	−0.0032 (6)	0.0050 (6)	0.0045 (6)
C17	0.0409 (10)	0.0180 (7)	0.0256 (8)	−0.0041 (7)	0.0095 (7)	0.0018 (6)
C18	0.0434 (10)	0.0244 (8)	0.0276 (9)	−0.0172 (8)	0.0004 (8)	0.0012 (7)
C19	0.0237 (8)	0.0356 (10)	0.0358 (10)	−0.0118 (7)	−0.0023 (7)	0.0051 (8)
C20	0.0207 (8)	0.0257 (8)	0.0283 (8)	−0.0022 (6)	0.0037 (6)	0.0044 (7)

Geometric parameters (Å, º)

As—O1	1.7267 (10)	C7—C8	1.5044 (19)
As—O2	1.6730 (10)	C8—C9	1.395 (2)
As—O3	1.6699 (10)	C8—C13	1.392 (2)
As—C1	1.8955 (13)	C9—H9	0.9500
O1—H1	0.83 (3)	C9—C10	1.386 (2)
N2—H2A	0.84 (2)	C10—H10	0.9500
N2—H2B	0.83 (2)	C10—C11	1.389 (2)
N2—C4	1.3776 (19)	C11—H11	0.9500
C1—C2	1.3978 (19)	C11—C12	1.385 (2)
C1—C6	1.3957 (19)	C12—H12	0.9500
C2—H2	0.9500	C12—C13	1.392 (2)
C2—C3	1.384 (2)	C13—H13	0.9500
C3—H3	0.9500	C14—H14A	0.9900
C3—C4	1.406 (2)	C14—H14B	0.9900
C4—C5	1.401 (2)	C14—C15	1.506 (2)
C5—H5	0.9500	C15—C16	1.387 (2)
C5—C6	1.391 (2)	C15—C20	1.396 (2)
C6—H6	0.9500	C16—H16	0.9500
O4—H4A	0.8696	C16—C17	1.391 (2)
O4—H4B	0.8701	C17—H17	0.9500
N1—H1A	0.9100	C17—C18	1.380 (3)
N1—H1B	0.9100	C18—H18	0.9500
N1—C7	1.4939 (17)	C18—C19	1.386 (3)
N1—C14	1.4995 (18)	C19—H19	0.9500
C7—H7A	0.9900	C19—C20	1.387 (2)
C7—H7B	0.9900	C20—H20	0.9500
O1—As—C1	103.71 (6)	C13—C8—C7	120.22 (13)
O2—As—O1	110.71 (5)	C13—C8—C9	119.09 (13)
O2—As—C1	110.47 (6)	C8—C9—H9	119.7
O3—As—O1	108.46 (5)	C10—C9—C8	120.55 (13)
O3—As—O2	111.48 (5)	C10—C9—H9	119.7
O3—As—C1	111.73 (5)	C9—C10—H10	120.0
As—O1—H1	113.0 (19)	C9—C10—C11	120.09 (14)
H2A—N2—H2B	116.7 (18)	C11—C10—H10	120.0
C4—N2—H2A	116.7 (13)	C10—C11—H11	120.1
C4—N2—H2B	116.7 (13)	C12—C11—C10	119.73 (14)
C2—C1—As	119.52 (10)	C12—C11—H11	120.1
C6—C1—As	121.39 (10)	C11—C12—H12	119.8
C6—C1—C2	119.08 (13)	C11—C12—C13	120.33 (14)
C1—C2—H2	119.6	C13—C12—H12	119.8
C3—C2—C1	120.83 (13)	C8—C13—H13	119.9
C3—C2—H2	119.6	C12—C13—C8	120.20 (14)
C2—C3—H3	119.8	C12—C13—H13	119.9
C2—C3—C4	120.33 (13)	N1—C14—H14A	109.2
C4—C3—H3	119.8	N1—C14—H14B	109.2
N2—C4—C3	120.31 (13)	N1—C14—C15	111.83 (12)
N2—C4—C5	120.99 (13)	H14A—C14—H14B	107.9
C5—C4—C3	118.69 (13)	C15—C14—H14A	109.2
C4—C5—H5	119.7	C15—C14—H14B	109.2
C6—C5—C4	120.62 (13)	C16—C15—C14	119.86 (14)
C6—C5—H5	119.7	C16—C15—C20	119.40 (14)
C1—C6—H6	119.8	C20—C15—C14	120.73 (14)
C5—C6—C1	120.37 (13)	C15—C16—H16	119.8
C5—C6—H6	119.8	C15—C16—C17	120.45 (15)
H4A—O4—H4B	104.5	C17—C16—H16	119.8
H1A—N1—H1B	107.7	C16—C17—H17	120.1
C7—N1—H1A	108.8	C18—C17—C16	119.86 (16)
C7—N1—H1B	108.8	C18—C17—H17	120.1
C7—N1—C14	113.62 (11)	C17—C18—H18	119.9
C14—N1—H1A	108.8	C17—C18—C19	120.13 (16)
C14—N1—H1B	108.8	C19—C18—H18	119.9
N1—C7—H7A	109.4	C18—C19—H19	119.9
N1—C7—H7B	109.4	C18—C19—C20	120.25 (16)
N1—C7—C8	111.30 (11)	C20—C19—H19	119.9
H7A—C7—H7B	108.0	C15—C20—H20	120.0
C8—C7—H7A	109.4	C19—C20—C15	119.91 (16)
C8—C7—H7B	109.4	C19—C20—H20	120.0
C9—C8—C7	120.67 (13)
As—C1—C2—C3	177.66 (11)	N1—C14—C15—C20	74.49 (17)
As—C1—C6—C5	−178.33 (10)	C7—N1—C14—C15	57.65 (16)
O1—As—C1—C2	−44.30 (12)	C7—C8—C9—C10	178.70 (13)
O1—As—C1—C6	135.23 (11)	C7—C8—C13—C12	−178.27 (14)
O2—As—C1—C2	−162.96 (10)	C8—C9—C10—C11	−0.3 (2)
O2—As—C1—C6	16.57 (13)	C9—C8—C13—C12	0.3 (2)
O3—As—C1—C2	72.32 (12)	C9—C10—C11—C12	0.0 (2)
O3—As—C1—C6	−108.15 (11)	C10—C11—C12—C13	0.4 (3)
N2—C4—C5—C6	178.11 (13)	C11—C12—C13—C8	−0.6 (2)
C1—C2—C3—C4	0.1 (2)	C13—C8—C9—C10	0.2 (2)
C2—C1—C6—C5	1.2 (2)	C14—N1—C7—C8	−178.14 (11)
C2—C3—C4—N2	−178.78 (13)	C14—C15—C16—C17	179.01 (14)
C2—C3—C4—C5	2.3 (2)	C14—C15—C20—C19	−179.17 (15)
C3—C4—C5—C6	−3.0 (2)	C15—C16—C17—C18	0.1 (2)
C4—C5—C6—C1	1.3 (2)	C16—C15—C20—C19	−0.1 (2)
C6—C1—C2—C3	−1.9 (2)	C16—C17—C18—C19	0.0 (3)
N1—C7—C8—C9	60.72 (17)	C17—C18—C19—C20	−0.2 (3)
N1—C7—C8—C13	−120.76 (14)	C18—C19—C20—C15	0.2 (3)
N1—C14—C15—C16	−104.55 (16)	C20—C15—C16—C17	0.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4^i	0.84 (2)	2.37 (2)	3.165 (2)	158.0 (18)
N2—H2B···O1^ii	0.83 (2)	2.25 (2)	3.0769 (17)	175.6 (18)
N1—H1A···O3	0.91	1.78	2.6842 (16)	172
N1—H1B···O3^iii	0.91	1.89	2.7260 (15)	151
O1—H1···O2^iv	0.83 (3)	1.73 (3)	2.5445 (15)	170 (3)
O4—H4A···O2^v	0.87	1.95	2.8074 (18)	169

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