3,4,5-Trimethoxy-benzohydrazidium chloride.

The title compound, C(10)H(15)N(2)O(4) (+)·Cl(-), was obtained as an unexpected by-product during the synthesis of 1-[2-(substituted ar-yl)]-3-methyl-pyrazol-5-ones. The hydrazide group is essentially planar, with an r.s.m. deviation of 0.020 (2) Å, and is oriented at a dihedral angle of 30.52 (3)° with respect to the benzene ring. In the crystal structure, the cations and anions are linked through N-H⋯O and N-H⋯Cl hydrogen bonds, forming a mol-ecular tape running along the b axis.

Related literature

For general background, see: Jin et al. (2006 ▶); Song et al. (2005 ▶); Yang et al. (2007 ▶). For a related structure, see: Zareef et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H15N2O4 +·Cl−

M = 262.69

Monoclinic,

a = 38.587 (3) Å

b = 4.8202 (3) Å

c = 13.5915 (10) Å

β = 108.459 (2)°

V = 2397.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.32 mm−1

T = 223 (1) K

0.29 × 0.28 × 0.05 mm

Data collection

Rigaku R-AXIS RAPIDII diffractometer

Absorption correction: numerical (ABSCOR; Higashi, 1999 ▶) T min = 0.930, T max = 0.984

15536 measured reflections

3483 independent reflections

2987 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.111

S = 1.06

3483 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.19 e Å−3

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036301/hk2567sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036301/hk2567Isup2.hkl

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

C10H15N2O4+·Cl–	F000 = 1104.00
Mr = 262.69	Dx = 1.455 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71075 Å
Hall symbol: -C 2yc	Cell parameters from 12804 reflections
a = 38.587 (3) Å	θ = 3.0–30.0º
b = 4.8202 (3) Å	µ = 0.32 mm−1
c = 13.5915 (10) Å	T = 223 (1) K
β = 108.459 (2)º	Platelet, colorless
V = 2397.9 (3) Å3	0.29 × 0.28 × 0.05 mm
Z = 8

Rigaku R-AXIS RAPIDII diffractometer	3483 independent reflections
Detector resolution: 10.00 pixels mm-1	2987 reflections with I > 2σ(I)
T = 223(2) K	Rint = 0.035
ω scans	θmax = 30.0º
Absorption correction: numerical(ABSCOR; Higashi, 1999)	h = −54→50
Tmin = 0.930, Tmax = 0.984	k = −6→6
15536 measured reflections	l = −19→19

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0672P)2 + 0.9082P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.003
3483 reflections	Δρmax = 0.51 e Å−3
158 parameters	Δρmin = −0.19 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
Cl1	0.531194 (8)	0.74543 (6)	0.14789 (2)	0.02591 (11)
O1	0.29508 (2)	−0.1702 (2)	0.04400 (7)	0.0261 (2)
O2	0.29359 (2)	0.12014 (18)	0.20875 (7)	0.02407 (19)
O3	0.35072 (3)	0.4308 (2)	0.31676 (7)	0.0301 (2)
O4	0.43237 (2)	−0.16714 (18)	0.07270 (7)	0.02515 (19)
N1	0.44683 (3)	0.2704 (2)	0.12743 (9)	0.0220 (2)
N2	0.47777 (3)	0.24854 (19)	0.09232 (9)	0.0222 (2)
H2NA	0.4900	0.0916	0.1173	0.033*
H2NB	0.4925	0.3956	0.1150	0.033*
H2NC	0.4703	0.2446	0.0225	0.033*
C1	0.38998 (3)	0.0818 (2)	0.13600 (9)	0.0198 (2)
C2	0.35979 (3)	−0.0716 (2)	0.07763 (9)	0.0207 (2)
H2	0.3616	−0.1909	0.0248	0.025*
C3	0.32687 (3)	−0.0453 (2)	0.09891 (8)	0.0204 (2)
C4	0.32509 (3)	0.1212 (2)	0.18165 (9)	0.0209 (2)
C5	0.35556 (3)	0.2748 (2)	0.23870 (9)	0.0217 (2)
C6	0.38830 (3)	0.2592 (2)	0.21544 (9)	0.0212 (2)
H6	0.4087	0.3656	0.2524	0.025*
C7	0.42422 (3)	0.0465 (2)	0.10930 (8)	0.0189 (2)
C8	0.29543 (4)	−0.3376 (3)	−0.04212 (10)	0.0302 (3)
H8A	0.3035	−0.2270	−0.0904	0.045*
H8B	0.2710	−0.4073	−0.0767	0.045*
H8C	0.3120	−0.4923	−0.0179	0.045*
C9	0.27160 (4)	0.3649 (3)	0.17816 (11)	0.0297 (3)
H9A	0.2862	0.5274	0.2066	0.045*
H9B	0.2509	0.3552	0.2041	0.045*
H9C	0.2628	0.3775	0.1031	0.045*
C10	0.38005 (4)	0.6091 (3)	0.37142 (10)	0.0311 (3)
H10A	0.4011	0.4981	0.4084	0.047*
H10B	0.3726	0.7210	0.4205	0.047*
H10C	0.3864	0.7294	0.3225	0.047*
H1	0.4380 (5)	0.439 (4)	0.1231 (14)	0.039 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.02223 (16)	0.02581 (17)	0.02881 (17)	−0.00046 (9)	0.00682 (12)	−0.00128 (10)
O1	0.0225 (4)	0.0335 (5)	0.0239 (4)	−0.0077 (3)	0.0095 (3)	−0.0079 (4)
O2	0.0240 (4)	0.0253 (4)	0.0279 (4)	−0.0016 (3)	0.0153 (3)	0.0007 (3)
O3	0.0292 (4)	0.0377 (5)	0.0280 (4)	−0.0087 (4)	0.0158 (4)	−0.0148 (4)
O4	0.0266 (4)	0.0200 (4)	0.0313 (5)	−0.0006 (3)	0.0127 (4)	−0.0037 (3)
N1	0.0220 (5)	0.0169 (5)	0.0317 (5)	−0.0004 (3)	0.0149 (4)	−0.0014 (4)
N2	0.0214 (5)	0.0202 (5)	0.0280 (5)	−0.0019 (3)	0.0122 (4)	−0.0009 (4)
C1	0.0209 (5)	0.0190 (5)	0.0213 (5)	0.0004 (4)	0.0092 (4)	0.0015 (4)
C2	0.0234 (5)	0.0199 (5)	0.0208 (5)	−0.0012 (4)	0.0099 (4)	−0.0010 (4)
C3	0.0218 (5)	0.0207 (5)	0.0195 (5)	−0.0028 (4)	0.0074 (4)	0.0005 (4)
C4	0.0216 (5)	0.0228 (5)	0.0213 (5)	−0.0010 (4)	0.0109 (4)	0.0008 (4)
C5	0.0246 (6)	0.0229 (5)	0.0199 (5)	−0.0010 (4)	0.0103 (4)	−0.0022 (4)
C6	0.0216 (5)	0.0215 (5)	0.0217 (5)	−0.0025 (4)	0.0086 (4)	−0.0020 (4)
C7	0.0202 (5)	0.0180 (5)	0.0186 (5)	0.0010 (4)	0.0062 (4)	0.0019 (4)
C8	0.0284 (6)	0.0371 (7)	0.0255 (6)	−0.0072 (5)	0.0092 (5)	−0.0091 (5)
C9	0.0275 (6)	0.0294 (6)	0.0358 (7)	0.0029 (5)	0.0152 (5)	0.0030 (5)
C10	0.0328 (6)	0.0344 (7)	0.0274 (6)	−0.0074 (5)	0.0112 (5)	−0.0118 (5)

O1—C3	1.3581 (14)	C2—C3	1.3950 (15)
O1—C8	1.4251 (15)	C2—H2	0.9400
O2—C4	1.3771 (13)	C3—C4	1.4009 (15)
O2—C9	1.4356 (16)	C4—C5	1.3982 (16)
O3—C5	1.3605 (14)	C5—C6	1.3981 (16)
O3—C10	1.4280 (15)	C6—H6	0.9400
O4—C7	1.2271 (14)	C8—H8A	0.9700
N1—C7	1.3602 (14)	C8—H8B	0.9700
N1—N2	1.4230 (13)	C8—H8C	0.9700
N1—H1	0.876 (19)	C9—H9A	0.9700
N2—H2NA	0.9000	C9—H9B	0.9700
N2—H2NB	0.9000	C9—H9C	0.9700
N2—H2NC	0.9000	C10—H10A	0.9700
C1—C6	1.3947 (15)	C10—H10B	0.9700
C1—C2	1.3958 (15)	C10—H10C	0.9700
C1—C7	1.4867 (15)
C3—O1—C8	117.43 (9)	C4—C5—C6	120.52 (10)
C4—O2—C9	114.20 (9)	C1—C6—C5	118.34 (10)
C5—O3—C10	117.16 (9)	C1—C6—H6	120.8
C7—N1—N2	116.00 (9)	C5—C6—H6	120.8
C7—N1—H1	120.7 (11)	O4—C7—N1	120.50 (10)
N2—N1—H1	113.3 (11)	O4—C7—C1	123.82 (10)
N1—N2—H2NA	109.5	N1—C7—C1	115.68 (10)
N1—N2—H2NB	109.5	O1—C8—H8A	109.5
H2NA—N2—H2NB	109.5	O1—C8—H8B	109.5
N1—N2—H2NC	109.5	H8A—C8—H8B	109.5
H2NA—N2—H2NC	109.5	O1—C8—H8C	109.5
H2NB—N2—H2NC	109.5	H8A—C8—H8C	109.5
C6—C1—C2	121.99 (10)	H8B—C8—H8C	109.5
C6—C1—C7	121.46 (10)	O2—C9—H9A	109.5
C2—C1—C7	116.55 (10)	O2—C9—H9B	109.5
C3—C2—C1	119.01 (10)	H9A—C9—H9B	109.5
C3—C2—H2	120.5	O2—C9—H9C	109.5
C1—C2—H2	120.5	H9A—C9—H9C	109.5
O1—C3—C2	124.68 (10)	H9B—C9—H9C	109.5
O1—C3—C4	115.46 (10)	O3—C10—H10A	109.5
C2—C3—C4	119.86 (10)	O3—C10—H10B	109.5
O2—C4—C5	120.82 (10)	H10A—C10—H10B	109.5
O2—C4—C3	118.97 (10)	O3—C10—H10C	109.5
C5—C4—C3	120.13 (10)	H10A—C10—H10C	109.5
O3—C5—C4	115.21 (10)	H10B—C10—H10C	109.5
O3—C5—C6	124.26 (11)
C6—C1—C2—C3	0.46 (17)	O2—C4—C5—O3	−3.67 (16)
C7—C1—C2—C3	−179.61 (10)	C3—C4—C5—O3	179.53 (10)
C8—O1—C3—C2	−0.71 (17)	O2—C4—C5—C6	175.34 (10)
C8—O1—C3—C4	178.87 (11)	C3—C4—C5—C6	−1.46 (17)
C1—C2—C3—O1	175.98 (10)	C2—C1—C6—C5	2.13 (17)
C1—C2—C3—C4	−3.58 (16)	C7—C1—C6—C5	−177.79 (10)
C9—O2—C4—C5	77.58 (14)	O3—C5—C6—C1	177.30 (11)
C9—O2—C4—C3	−105.59 (12)	C4—C5—C6—C1	−1.62 (17)
O1—C3—C4—O2	7.64 (15)	N2—N1—C7—O4	5.88 (16)
C2—C3—C4—O2	−172.76 (10)	N2—N1—C7—C1	−173.78 (10)
O1—C3—C4—C5	−175.50 (10)	C6—C1—C7—O4	150.77 (11)
C2—C3—C4—C5	4.09 (17)	C2—C1—C7—O4	−29.15 (16)
C10—O3—C5—C4	−174.81 (11)	C6—C1—C7—N1	−29.58 (15)
C10—O3—C5—C6	6.22 (18)	C2—C1—C7—N1	150.50 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4i	0.876 (19)	2.007 (19)	2.8200 (13)	154.0 (18)
N2—H2NA···Cl1ii	0.90	2.25	3.1169 (11)	162
N2—H2NB···Cl1	0.90	2.20	3.0937 (11)	171
N2—H2NC···Cl1iii	0.90	2.30	3.1724 (12)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.876 (19)	2.007 (19)	2.8200 (13)	154.0 (18)
N2—H2NA⋯Cl1ii	0.90	2.25	3.1169 (11)	162
N2—H2NB⋯Cl1	0.90	2.20	3.0937 (11)	171
N2—H2NC⋯Cl1iii	0.90	2.30	3.1724 (12)	164

Symmetry codes: (i) ; (ii) ; (iii) .