4-Benzhydryl-1-cinnamylpiperazin-1-ium nitrate.

In the title compound, C(26)H(29)N(2) (+)·NO(3) (-), the dihedral angle formed by the phenyl rings of the benzhydryl group is 66.18 (9)°. Crystal cohesion is enforced by cation-anion C-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For the use of amine derivatives in coordination chemisty, see: Manzur et al. (2007 ▶); Ismayilov et al. (2007 ▶); Austria et al. (2007 ▶).

Experimental

Crystal data

C26H29N2 +·NO3 −

M = 431.52

Monoclinic,

a = 18.6368 (17) Å

b = 10.8990 (10) Å

c = 12.0271 (10) Å

β = 107.397 (2)°

V = 2331.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.27 × 0.18 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.978, T max = 0.985

22444 measured reflections

5328 independent reflections

2413 reflections with I > 2σ(I)

R int = 0.100

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.178

S = 1.03

5328 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019958/rz2224sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019958/rz2224Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H29N2+·NO3–	F000 = 920
Mr = 431.52	Dx = 1.230 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 1178 reflections
a = 18.6368 (17) Å	θ = 2.3–24.4º
b = 10.8990 (10) Å	µ = 0.08 mm−1
c = 12.0271 (10) Å	T = 293 (2) K
β = 107.397 (2)º	Block, colourless
V = 2331.2 (4) Å3	0.27 × 0.18 × 0.15 mm
Z = 4

Rigaku Mercury2 (2x2 bin mode) diffractometer	5328 independent reflections
Radiation source: fine-focus sealed tube	2413 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.100
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 3.0º
ω scans	h = −24→24
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −14→14
Tmin = 0.978, Tmax = 0.985	l = −15→15
22444 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.071	H-atom parameters constrained
wR(F2) = 0.178	w = 1/[σ2(Fo2) + (0.0622P)2 + 0.0525P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
5328 reflections	Δρmax = 0.15 e Å−3
289 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
N1	0.31523 (11)	0.58781 (18)	0.45974 (16)	0.0422 (5)
N2	0.30973 (11)	0.42385 (18)	0.26651 (16)	0.0460 (6)
H2N	0.3154	0.3503	0.3020	0.055*
C1	0.31968 (14)	0.6166 (2)	0.5816 (2)	0.0437 (6)
H1	0.3244	0.5391	0.6244	0.052*
C2	0.38828 (13)	0.6943 (2)	0.6397 (2)	0.0383 (6)
C3	0.42973 (14)	0.6712 (2)	0.7539 (2)	0.0468 (7)
H3	0.4148	0.6086	0.7947	0.056*
C4	0.49302 (15)	0.7395 (3)	0.8085 (2)	0.0561 (8)
H4	0.5204	0.7228	0.8853	0.067*
C5	0.51513 (15)	0.8324 (3)	0.7483 (3)	0.0582 (8)
H5	0.5581	0.8777	0.7840	0.070*
C6	0.47373 (16)	0.8579 (3)	0.6358 (2)	0.0569 (7)
H6	0.4883	0.9218	0.5960	0.068*
C7	0.41097 (15)	0.7900 (2)	0.5814 (2)	0.0479 (7)
H7	0.3834	0.8081	0.5050	0.057*
C8	0.24792 (14)	0.6793 (2)	0.5869 (2)	0.0468 (7)
C9	0.21408 (16)	0.7710 (3)	0.5104 (2)	0.0575 (8)
H9	0.2360	0.7974	0.4546	0.069*
C10	0.14769 (17)	0.8243 (3)	0.5158 (3)	0.0713 (9)
H10	0.1256	0.8865	0.4641	0.086*
C11	0.11438 (18)	0.7855 (4)	0.5974 (3)	0.0812 (11)
H11	0.0689	0.8190	0.5993	0.097*
C12	0.1490 (2)	0.6975 (4)	0.6754 (3)	0.0869 (11)
H12	0.1279	0.6736	0.7331	0.104*
C13	0.21470 (17)	0.6434 (3)	0.6702 (3)	0.0683 (9)
H13	0.2369	0.5822	0.7232	0.082*
C14	0.38274 (14)	0.5241 (2)	0.4509 (2)	0.0486 (7)
H14A	0.3885	0.4472	0.4933	0.058*
H14B	0.4267	0.5741	0.4862	0.058*
C15	0.37754 (14)	0.4990 (2)	0.3257 (2)	0.0512 (7)
H15A	0.3752	0.5763	0.2848	0.061*
H15B	0.4224	0.4559	0.3224	0.061*
C16	0.24141 (14)	0.4834 (2)	0.2819 (2)	0.0509 (7)
H16A	0.1981	0.4309	0.2499	0.061*
H16B	0.2324	0.5605	0.2396	0.061*
C17	0.25099 (15)	0.5069 (2)	0.4092 (2)	0.0511 (7)
H17A	0.2056	0.5443	0.4175	0.061*
H17B	0.2586	0.4295	0.4510	0.061*
C18	0.30351 (17)	0.4038 (3)	0.1408 (2)	0.0609 (8)
H18A	0.2982	0.4827	0.1018	0.073*
H18B	0.3497	0.3665	0.1355	0.073*
C19	0.23928 (16)	0.3248 (3)	0.0793 (2)	0.0593 (8)
H19	0.2316	0.2531	0.1161	0.071*
C20	0.19265 (16)	0.3493 (3)	−0.0233 (2)	0.0628 (8)
H20	0.1975	0.4255	−0.0550	0.075*
C21	0.13313 (17)	0.2680 (3)	−0.0937 (3)	0.0636 (8)
C22	0.10066 (18)	0.2921 (3)	−0.2118 (3)	0.0828 (11)
H22	0.1139	0.3635	−0.2432	0.099*
C23	0.0498 (2)	0.2140 (5)	−0.2832 (4)	0.1048 (14)
H23	0.0300	0.2314	−0.3622	0.126*
C24	0.0283 (2)	0.1098 (5)	−0.2373 (4)	0.1075 (15)
H24	−0.0062	0.0564	−0.2854	0.129*
C25	0.0578 (2)	0.0840 (4)	−0.1204 (4)	0.0945 (12)
H25	0.0431	0.0137	−0.0893	0.113*
C26	0.10931 (17)	0.1634 (3)	−0.0498 (3)	0.0749 (10)
H26	0.1285	0.1462	0.0293	0.090*
O1	0.29203 (17)	0.1418 (2)	0.2790 (2)	0.1197 (10)
O2	0.35493 (15)	0.0310 (2)	0.4192 (2)	0.0982 (9)
O3	0.36372 (13)	0.2268 (2)	0.42714 (19)	0.0849 (7)
N3	0.33744 (15)	0.1316 (3)	0.3756 (2)	0.0622 (7)

	U11	U22	U33	U12	U13	U23
N1	0.0398 (13)	0.0489 (13)	0.0382 (12)	−0.0055 (10)	0.0118 (9)	−0.0046 (10)
N2	0.0558 (15)	0.0439 (13)	0.0385 (13)	−0.0008 (11)	0.0143 (10)	−0.0009 (10)
C1	0.0532 (17)	0.0407 (15)	0.0381 (15)	−0.0041 (12)	0.0151 (12)	−0.0006 (12)
C2	0.0403 (15)	0.0397 (15)	0.0359 (15)	−0.0006 (11)	0.0127 (11)	−0.0034 (11)
C3	0.0532 (18)	0.0455 (16)	0.0401 (16)	0.0042 (13)	0.0114 (13)	0.0018 (12)
C4	0.0506 (19)	0.070 (2)	0.0406 (17)	0.0096 (15)	0.0022 (13)	−0.0071 (15)
C5	0.0488 (18)	0.065 (2)	0.060 (2)	−0.0100 (15)	0.0149 (15)	−0.0179 (16)
C6	0.062 (2)	0.0584 (18)	0.0545 (19)	−0.0135 (15)	0.0245 (15)	−0.0067 (15)
C7	0.0544 (18)	0.0495 (16)	0.0373 (15)	−0.0059 (13)	0.0101 (12)	0.0002 (12)
C8	0.0466 (16)	0.0524 (17)	0.0412 (16)	−0.0062 (13)	0.0127 (13)	−0.0071 (13)
C9	0.0512 (19)	0.063 (2)	0.0585 (19)	0.0032 (15)	0.0174 (14)	−0.0024 (15)
C10	0.057 (2)	0.075 (2)	0.073 (2)	0.0049 (17)	0.0044 (17)	−0.0085 (17)
C11	0.045 (2)	0.118 (3)	0.078 (3)	0.005 (2)	0.0148 (19)	−0.025 (2)
C12	0.065 (2)	0.133 (3)	0.071 (2)	−0.007 (2)	0.0333 (19)	−0.008 (2)
C13	0.058 (2)	0.092 (2)	0.058 (2)	−0.0034 (17)	0.0229 (16)	0.0073 (17)
C14	0.0478 (18)	0.0520 (17)	0.0444 (17)	−0.0014 (13)	0.0112 (13)	−0.0062 (13)
C15	0.0487 (18)	0.0570 (18)	0.0492 (18)	−0.0074 (13)	0.0168 (13)	−0.0066 (13)
C16	0.0438 (17)	0.0532 (17)	0.0530 (18)	−0.0005 (13)	0.0102 (13)	−0.0064 (13)
C17	0.0460 (17)	0.0564 (18)	0.0512 (17)	−0.0112 (13)	0.0149 (12)	−0.0099 (14)
C18	0.074 (2)	0.074 (2)	0.0351 (17)	0.0019 (16)	0.0172 (14)	−0.0052 (14)
C19	0.070 (2)	0.064 (2)	0.0401 (17)	0.0021 (16)	0.0108 (15)	−0.0114 (14)
C20	0.069 (2)	0.064 (2)	0.055 (2)	0.0096 (16)	0.0179 (16)	−0.0050 (15)
C21	0.0481 (19)	0.080 (2)	0.060 (2)	0.0171 (16)	0.0123 (16)	−0.0114 (17)
C22	0.067 (2)	0.105 (3)	0.064 (2)	0.010 (2)	−0.0004 (17)	−0.006 (2)
C23	0.071 (3)	0.151 (4)	0.074 (3)	−0.005 (3)	−0.005 (2)	−0.021 (3)
C24	0.056 (3)	0.155 (4)	0.102 (4)	−0.007 (3)	0.008 (2)	−0.049 (3)
C25	0.060 (2)	0.115 (3)	0.110 (3)	−0.007 (2)	0.028 (2)	−0.024 (3)
C26	0.060 (2)	0.095 (3)	0.068 (2)	0.0024 (19)	0.0161 (17)	−0.017 (2)
O1	0.144 (2)	0.121 (2)	0.0685 (17)	−0.0040 (18)	−0.0074 (17)	0.0157 (16)
O2	0.163 (3)	0.0587 (14)	0.0891 (18)	0.0367 (15)	0.0623 (16)	0.0238 (13)
O3	0.105 (2)	0.0611 (15)	0.0901 (17)	−0.0110 (13)	0.0315 (14)	−0.0119 (13)
N3	0.0805 (19)	0.0556 (17)	0.0572 (18)	0.0114 (15)	0.0309 (14)	0.0090 (15)

N1—C17	1.465 (3)	C14—C15	1.505 (3)
N1—C14	1.468 (3)	C14—H14A	0.9700
N1—C1	1.477 (3)	C14—H14B	0.9700
N2—C16	1.489 (3)	C15—H15A	0.9700
N2—C18	1.498 (3)	C15—H15B	0.9700
N2—C15	1.496 (3)	C16—C17	1.510 (3)
N2—H2N	0.9001	C16—H16A	0.9700
C1—C8	1.520 (3)	C16—H16B	0.9700
C1—C2	1.518 (3)	C17—H17A	0.9700
C1—H1	0.9800	C17—H17B	0.9700
C2—C3	1.382 (3)	C18—C19	1.480 (4)
C2—C7	1.391 (3)	C18—H18A	0.9700
C3—C4	1.383 (3)	C18—H18B	0.9700
C3—H3	0.9300	C19—C20	1.307 (3)
C4—C5	1.377 (4)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.473 (4)
C5—C6	1.371 (4)	C20—H20	0.9300
C5—H5	0.9300	C21—C26	1.385 (4)
C6—C7	1.374 (3)	C21—C22	1.392 (4)
C6—H6	0.9300	C22—C23	1.369 (4)
C7—H7	0.9300	C22—H22	0.9300
C8—C9	1.377 (3)	C23—C24	1.374 (5)
C8—C13	1.382 (4)	C23—H23	0.9300
C9—C10	1.386 (4)	C24—C25	1.377 (5)
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.375 (4)	C25—C26	1.380 (4)
C10—H10	0.9300	C25—H25	0.9300
C11—C12	1.362 (4)	C26—H26	0.9300
C11—H11	0.9300	O1—N3	1.221 (3)
C12—C13	1.378 (4)	O2—N3	1.217 (3)
C12—H12	0.9300	O3—N3	1.233 (3)
C13—H13	0.9300
C17—N1—C14	107.27 (19)	N1—C14—H14B	109.4
C17—N1—C1	109.66 (19)	C15—C14—H14B	109.4
C14—N1—C1	112.15 (18)	H14A—C14—H14B	108.0
C16—N2—C18	112.2 (2)	N2—C15—C14	111.6 (2)
C16—N2—C15	109.51 (19)	N2—C15—H15A	109.3
C18—N2—C15	111.1 (2)	C14—C15—H15A	109.3
C16—N2—H2N	108.2	N2—C15—H15B	109.3
C18—N2—H2N	108.2	C14—C15—H15B	109.3
C15—N2—H2N	107.4	H15A—C15—H15B	108.0
N1—C1—C8	110.39 (19)	N2—C16—C17	110.7 (2)
N1—C1—C2	111.41 (19)	N2—C16—H16A	109.5
C8—C1—C2	111.1 (2)	C17—C16—H16A	109.5
N1—C1—H1	107.9	N2—C16—H16B	109.5
C8—C1—H1	107.9	C17—C16—H16B	109.5
C2—C1—H1	107.9	H16A—C16—H16B	108.1
C3—C2—C7	118.3 (2)	N1—C17—C16	110.9 (2)
C3—C2—C1	120.0 (2)	N1—C17—H17A	109.5
C7—C2—C1	121.8 (2)	C16—C17—H17A	109.5
C2—C3—C4	121.2 (2)	N1—C17—H17B	109.5
C2—C3—H3	119.4	C16—C17—H17B	109.5
C4—C3—H3	119.4	H17A—C17—H17B	108.0
C5—C4—C3	119.5 (3)	C19—C18—N2	113.3 (2)
C5—C4—H4	120.3	C19—C18—H18A	108.9
C3—C4—H4	120.3	N2—C18—H18A	108.9
C6—C5—C4	120.0 (3)	C19—C18—H18B	108.9
C6—C5—H5	120.0	N2—C18—H18B	108.9
C4—C5—H5	120.0	H18A—C18—H18B	107.7
C5—C6—C7	120.6 (3)	C20—C19—C18	124.3 (3)
C5—C6—H6	119.7	C20—C19—H19	117.9
C7—C6—H6	119.7	C18—C19—H19	117.9
C6—C7—C2	120.5 (2)	C19—C20—C21	126.4 (3)
C6—C7—H7	119.8	C19—C20—H20	116.8
C2—C7—H7	119.8	C21—C20—H20	116.8
C9—C8—C13	118.3 (3)	C26—C21—C22	117.0 (3)
C9—C8—C1	122.1 (2)	C26—C21—C20	123.2 (3)
C13—C8—C1	119.6 (2)	C22—C21—C20	119.7 (3)
C8—C9—C10	120.6 (3)	C23—C22—C21	122.0 (4)
C8—C9—H9	119.7	C23—C22—H22	119.0
C10—C9—H9	119.7	C21—C22—H22	119.0
C11—C10—C9	120.3 (3)	C22—C23—C24	119.5 (4)
C11—C10—H10	119.8	C22—C23—H23	120.2
C9—C10—H10	119.8	C24—C23—H23	120.2
C12—C11—C10	119.1 (3)	C23—C24—C25	120.2 (4)
C12—C11—H11	120.4	C23—C24—H24	119.9
C10—C11—H11	120.4	C25—C24—H24	119.9
C11—C12—C13	120.9 (3)	C24—C25—C26	119.5 (4)
C11—C12—H12	119.5	C24—C25—H25	120.2
C13—C12—H12	119.5	C26—C25—H25	120.2
C12—C13—C8	120.6 (3)	C25—C26—C21	121.6 (3)
C12—C13—H13	119.7	C25—C26—H26	119.2
C8—C13—H13	119.7	C21—C26—H26	119.2
N1—C14—C15	111.0 (2)	O2—N3—O1	120.8 (3)
N1—C14—H14A	109.4	O2—N3—O3	121.8 (3)
C15—C14—H14A	109.4	O1—N3—O3	117.4 (3)
C17—N1—C1—C8	−59.4 (3)	C9—C8—C13—C12	0.6 (4)
C14—N1—C1—C8	−178.4 (2)	C1—C8—C13—C12	−178.9 (3)
C17—N1—C1—C2	176.61 (19)	C17—N1—C14—C15	61.1 (3)
C14—N1—C1—C2	57.6 (3)	C1—N1—C14—C15	−178.4 (2)
N1—C1—C2—C3	−139.5 (2)	C16—N2—C15—C14	53.2 (3)
C8—C1—C2—C3	96.9 (3)	C18—N2—C15—C14	177.7 (2)
N1—C1—C2—C7	40.9 (3)	N1—C14—C15—N2	−58.1 (3)
C8—C1—C2—C7	−82.6 (3)	C18—N2—C16—C17	−177.7 (2)
C7—C2—C3—C4	−1.2 (4)	C15—N2—C16—C17	−53.8 (3)
C1—C2—C3—C4	179.2 (2)	C14—N1—C17—C16	−62.3 (3)
C2—C3—C4—C5	0.1 (4)	C1—N1—C17—C16	175.7 (2)
C3—C4—C5—C6	1.2 (4)	N2—C16—C17—N1	60.1 (3)
C4—C5—C6—C7	−1.3 (4)	C16—N2—C18—C19	−59.8 (3)
C5—C6—C7—C2	0.2 (4)	C15—N2—C18—C19	177.2 (2)
C3—C2—C7—C6	1.1 (4)	N2—C18—C19—C20	134.3 (3)
C1—C2—C7—C6	−179.4 (2)	C18—C19—C20—C21	172.9 (3)
N1—C1—C8—C9	−43.9 (3)	C19—C20—C21—C26	13.1 (5)
C2—C1—C8—C9	80.2 (3)	C19—C20—C21—C22	−163.8 (3)
N1—C1—C8—C13	135.6 (2)	C26—C21—C22—C23	−2.7 (5)
C2—C1—C8—C13	−100.2 (3)	C20—C21—C22—C23	174.4 (3)
C13—C8—C9—C10	−1.1 (4)	C21—C22—C23—C24	1.6 (6)
C1—C8—C9—C10	178.5 (2)	C22—C23—C24—C25	0.0 (6)
C8—C9—C10—C11	−0.5 (5)	C23—C24—C25—C26	−0.3 (6)
C9—C10—C11—C12	2.5 (5)	C24—C25—C26—C21	−0.9 (5)
C10—C11—C12—C13	−2.9 (5)	C22—C21—C26—C25	2.3 (5)
C11—C12—C13—C8	1.4 (5)	C20—C21—C26—C25	−174.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O3	0.90	2.02	2.862 (3)	156
N2—H2N···O1	0.90	2.31	3.101 (3)	146
C14—H14A···O3	0.97	2.53	3.263 (3)	132
C19—H19···O1	0.93	2.29	3.050 (4)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O3	0.90	2.02	2.862 (3)	156
N2—H2N⋯O1	0.90	2.31	3.101 (3)	146
C14—H14A⋯O3	0.97	2.53	3.263 (3)	132
C19—H19⋯O1	0.93	2.29	3.050 (4)	138