catena-Poly[[[diaqua­(1,10-phenanthroline-κ2N,N′)zinc]-μ-4-hy­droxy-3-sulfonato­benzoato-κ2O3:O1] sesquihydrate]

Fang, X.-Q.; Gao, S.; Ng, S.W.

doi:10.1107/S1600536812018740

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m722

doi:10.1107/S1600536812018740

Open

access

catena-Poly[[[diaqua(1,10-phenanthroline-κ²N,N′)zinc]-μ-4-hydroxy-3-sulfonatobenzoato-κ²O³:O¹] sesquihydrate]

Xiang-Qian Fang,^a Shan Gao ^a and Seik Weng Ng ^b,^c ^*

^aKey Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Heilongjiang University, Harbin 150080, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 23 April 2012; accepted 26 April 2012; online 2 May 2012)

The 1,10-phenanthroline-chelated Zn atom in the polymeric title compound, {[Zn(C₇H₄O₆S)(C₁₂H₈N₂)(H₂O)₂]·1.5H₂O}_n, is connected to the sulfonate O atom of one 4-hydroxy-3-sulfonatobenzoate dianion and to the carboxylate O atom of another dianion. It is also coordinated by two water molecules in an overall octahedral environment. The dianion links adjacent metal atoms into a chain running along [110]. The chains are linked by O—H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For the isostructural Mn^II derivative, see: Fang et al. (2011 ) and for the isostructural Co^II derivative, see: Fang et al. (2012 ).

Experimental

Crystal data

[Zn(C₇H₄O₆S)(C₁₂H₈N₂)(H₂O)₂]·1.5H₂O
M_r = 524.79
Monoclinic, C 2/c
a = 8.3682 (3) Å
b = 17.3251 (6) Å
c = 28.6686 (10) Å
β = 92.848 (1)°
V = 4151.2 (3) Å³
Z = 8
Mo Kα radiation
μ = 1.34 mm⁻¹
T = 293 K
0.19 × 0.15 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.784, T_max = 0.866
20011 measured reflections
4741 independent reflections
3098 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.104
S = 1.16
4741 reflections
326 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.88 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O4w	0.84 (1)	1.78 (1)	2.615 (3)	172 (4)
O1w—H11⋯O6ⁱ	0.84 (1)	1.68 (1)	2.520 (3)	172 (5)
O1w—H12⋯O3w	0.84 (1)	1.98 (2)	2.793 (2)	164 (4)
O2w—H21⋯O2ⁱⁱ	0.84 (1)	1.94 (1)	2.760 (3)	166 (4)
O2w—H22⋯O1wⁱⁱⁱ	0.84 (1)	1.93 (1)	2.767 (3)	174 (4)
O3w—H31⋯O2	0.84 (1)	1.95 (2)	2.752 (3)	160 (4)
O4w—H41⋯O4^iv	0.84 (1)	2.23 (3)	2.939 (3)	142 (4)
O4w—H42⋯O5^v	0.84 (1)	1.95 (1)	2.789 (3)	177 (4)
Symmetry codes: (i) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) x-1, y, z; (iii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (v) -x+2, -y+1, -z+1.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812018740/bt5893sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018740/bt5893Isup2.hkl

checkCIF report

Comment top

The title zinc compound (Scheme I, Fig. 1) is isostructural with the manganese(II) derivative (Fang et al., 2011) and with the cobalt(II) derivative (Fang et al., 2012). The 1,10-phenanthroline chelated Zn atom is connected to the sulfonate O atom of one (C₇H₄O₆S) dianion and to the carboxylate O atom of another dianion. It is also coordinated by two water molecules in an octahedral environment. The dianion links adjacent metal atoms into a chain along [1 1 0]. The chains are linked by O–H···O hydrogen bonds into a three-dimensional network (Table 1).

Related literature top

For the isostructural Mn^II derivative, see: Fang et al. (2011) and for the isostructural Co^II derivative, see: Fang et al. (2012).

Experimental top

A methanol solution (5 ml) of 1,10-phenanthroline (1 mmol) was added to an aqueous solution (10 ml) of zinc(II) dichloride (1 mmol), 2-hydroxy-5-carboxybenzenesulfonic acid (2 mmol) and lithium hydroxide (4 mmol). Colorless crystals were isolated from the solution after several days.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of a portion of the structure of polymeric [Zn(H₂O)₂(C₁₂H₈N₂)(C₇H₄O₆S)]_n^.1.5nH₂O at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

catena-Poly[[[diaqua(1,10-phenanthroline-κ²N,N')zinc]- µ-4-hydroxy-3-sulfonatobenzoato-κ²O³:O¹] sesquihydrate] top

Crystal data top

[Zn(C₇H₄O₆S)(C₁₂H₈N₂)(H₂O)₂]·1.5H₂O	F(000) = 2152
M_r = 524.79	D_x = 1.679 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 12500 reflections
a = 8.3682 (3) Å	θ = 3.0–27.5°
b = 17.3251 (6) Å	µ = 1.34 mm⁻¹
c = 28.6686 (10) Å	T = 293 K
β = 92.848 (1)°	Prism, colorless
V = 4151.2 (3) Å³	0.19 × 0.15 × 0.11 mm
Z = 8

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	4741 independent reflections
Radiation source: fine-focus sealed tube	3098 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ω scan	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
T_min = 0.784, T_max = 0.866	k = −18→22
20011 measured reflections	l = −37→37

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ²(F_o²) + (0.0376P)² + 5.6207P] where P = (F_o² + 2F_c²)/3
4741 reflections	(Δ/σ)_max = 0.001
326 parameters	Δρ_max = 0.62 e Å⁻³
8 restraints	Δρ_min = −0.88 e Å⁻³

Crystal data top

[Zn(C₇H₄O₆S)(C₁₂H₈N₂)(H₂O)₂]·1.5H₂O	V = 4151.2 (3) Å³
M_r = 524.79	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 8.3682 (3) Å	µ = 1.34 mm⁻¹
b = 17.3251 (6) Å	T = 293 K
c = 28.6686 (10) Å	0.19 × 0.15 × 0.11 mm
β = 92.848 (1)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	4741 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3098 reflections with I > 2σ(I)
T_min = 0.784, T_max = 0.866	R_int = 0.051
20011 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	8 restraints
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	Δρ_max = 0.62 e Å⁻³
4741 reflections	Δρ_min = −0.88 e Å⁻³
326 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.61591 (4)	0.232574 (19)	0.342240 (11)	0.02942 (12)
S1	1.01800 (9)	0.26433 (4)	0.37668 (3)	0.02952 (18)
O1	0.8591 (2)	0.23027 (12)	0.37134 (7)	0.0340 (5)
O2	1.0907 (3)	0.27321 (13)	0.33170 (8)	0.0489 (7)
O3	1.1182 (3)	0.22346 (14)	0.41081 (9)	0.0523 (7)
O4	0.8751 (3)	0.31120 (12)	0.46469 (7)	0.0415 (6)
O5	1.0863 (3)	0.62949 (11)	0.37689 (7)	0.0331 (5)
O6	1.1071 (3)	0.54964 (13)	0.31619 (8)	0.0518 (7)
O1W	0.6923 (3)	0.17550 (13)	0.28105 (7)	0.0314 (5)
O2W	0.3893 (3)	0.22125 (19)	0.30948 (9)	0.0579 (8)
O3W	1.0000	0.1982 (2)	0.2500	0.0491 (9)
O4W	0.7309 (3)	0.35044 (14)	0.53999 (8)	0.0421 (6)
N1	0.5209 (3)	0.30126 (15)	0.39576 (8)	0.0332 (6)
N2	0.6531 (3)	0.34633 (15)	0.31609 (9)	0.0374 (6)
C1	0.9919 (4)	0.35998 (16)	0.39722 (10)	0.0280 (6)
C2	0.9203 (4)	0.37230 (17)	0.43963 (10)	0.0313 (7)
C3	0.8988 (4)	0.44787 (18)	0.45453 (11)	0.0385 (8)
H3	0.8495	0.4571	0.4824	0.046*
C4	0.9496 (4)	0.50923 (17)	0.42853 (11)	0.0369 (8)
H4A	0.9348	0.5593	0.4392	0.044*
C5	1.0230 (4)	0.49733 (17)	0.38647 (10)	0.0318 (7)
C6	1.0417 (4)	0.42181 (17)	0.37114 (10)	0.0302 (7)
H6	1.0885	0.4128	0.3429	0.036*
C7	1.0760 (4)	0.56319 (17)	0.35757 (10)	0.0332 (7)
C8	0.5305 (4)	0.37811 (19)	0.38722 (11)	0.0377 (8)
C9	0.4569 (4)	0.2779 (2)	0.43478 (12)	0.0429 (8)
H9	0.4499	0.2252	0.4406	0.051*
C10	0.3996 (5)	0.3299 (3)	0.46746 (13)	0.0599 (12)
H10	0.3567	0.3118	0.4947	0.072*
C11	0.4075 (5)	0.4066 (3)	0.45891 (15)	0.0636 (12)
H11A	0.3691	0.4414	0.4803	0.076*
C12	0.4733 (5)	0.4339 (2)	0.41789 (14)	0.0517 (10)
C13	0.4894 (6)	0.5136 (2)	0.40649 (19)	0.0738 (14)
H13	0.4525	0.5509	0.4267	0.089*
C14	0.5563 (6)	0.5357 (2)	0.3673 (2)	0.0795 (15)
H14	0.5647	0.5881	0.3609	0.095*
C15	0.6156 (5)	0.4811 (2)	0.33509 (15)	0.0564 (11)
C16	0.6890 (6)	0.5010 (2)	0.29391 (17)	0.0740 (14)
H16	0.7015	0.5528	0.2862	0.089*
C17	0.7418 (6)	0.4454 (3)	0.26522 (15)	0.0701 (13)
H17	0.7913	0.4584	0.2380	0.084*
C18	0.7207 (5)	0.3679 (2)	0.27727 (12)	0.0506 (10)
H18	0.7555	0.3300	0.2572	0.061*
C19	0.6008 (4)	0.40212 (18)	0.34510 (11)	0.0376 (8)
H4	0.832 (5)	0.328 (2)	0.4885 (9)	0.066 (13)*
H11	0.665 (6)	0.1314 (13)	0.2903 (16)	0.092 (17)*
H12	0.7903 (16)	0.176 (2)	0.2762 (13)	0.054 (12)*
H21	0.301 (3)	0.232 (2)	0.3201 (14)	0.060 (12)*
H22	0.368 (5)	0.204 (2)	0.2826 (7)	0.066 (13)*
H31	1.023 (5)	0.2307 (17)	0.2710 (10)	0.055 (12)*
H41	0.669 (4)	0.3148 (17)	0.5466 (14)	0.064 (13)*
H42	0.784 (4)	0.358 (2)	0.5651 (8)	0.060 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0375 (2)	0.02202 (19)	0.02921 (19)	−0.00039 (15)	0.00628 (15)	−0.00082 (14)
S1	0.0306 (4)	0.0221 (4)	0.0363 (4)	−0.0016 (3)	0.0063 (3)	−0.0058 (3)
O1	0.0303 (11)	0.0265 (11)	0.0448 (12)	−0.0081 (9)	−0.0009 (10)	−0.0059 (9)
O2	0.0613 (16)	0.0375 (14)	0.0506 (14)	−0.0070 (12)	0.0310 (13)	−0.0130 (11)
O3	0.0504 (16)	0.0372 (14)	0.0673 (17)	0.0087 (12)	−0.0172 (13)	−0.0003 (12)
O4	0.0697 (17)	0.0242 (11)	0.0324 (12)	−0.0106 (11)	0.0196 (12)	−0.0017 (9)
O5	0.0482 (14)	0.0223 (11)	0.0292 (10)	−0.0077 (10)	0.0066 (10)	−0.0020 (9)
O6	0.094 (2)	0.0289 (13)	0.0343 (12)	−0.0179 (13)	0.0245 (13)	−0.0051 (10)
O1W	0.0369 (13)	0.0288 (12)	0.0295 (11)	−0.0043 (10)	0.0108 (10)	−0.0007 (9)
O2W	0.0366 (15)	0.100 (2)	0.0372 (14)	0.0095 (15)	0.0010 (13)	−0.0240 (15)
O3W	0.047 (2)	0.055 (2)	0.045 (2)	0.000	0.0070 (19)	0.000
O4W	0.0600 (17)	0.0377 (14)	0.0292 (12)	−0.0082 (12)	0.0086 (12)	−0.0005 (10)
N1	0.0329 (14)	0.0366 (15)	0.0302 (13)	0.0011 (12)	0.0038 (12)	−0.0056 (11)
N2	0.0476 (17)	0.0278 (14)	0.0372 (14)	0.0006 (12)	0.0052 (13)	0.0011 (11)
C1	0.0295 (16)	0.0228 (15)	0.0319 (15)	−0.0045 (12)	0.0043 (13)	−0.0046 (12)
C2	0.0408 (18)	0.0253 (15)	0.0283 (15)	−0.0090 (13)	0.0061 (14)	−0.0004 (12)
C3	0.058 (2)	0.0294 (17)	0.0296 (16)	−0.0062 (15)	0.0174 (16)	−0.0054 (13)
C4	0.055 (2)	0.0228 (16)	0.0336 (16)	−0.0083 (15)	0.0118 (16)	−0.0082 (13)
C5	0.0423 (19)	0.0231 (15)	0.0305 (15)	−0.0064 (13)	0.0067 (14)	−0.0005 (12)
C6	0.0371 (17)	0.0295 (16)	0.0249 (14)	−0.0059 (13)	0.0094 (13)	−0.0027 (12)
C7	0.0427 (19)	0.0251 (16)	0.0323 (16)	−0.0073 (14)	0.0069 (15)	−0.0047 (13)
C8	0.0375 (18)	0.0310 (17)	0.0438 (18)	0.0069 (14)	−0.0054 (15)	−0.0119 (15)
C9	0.0344 (18)	0.056 (2)	0.0386 (18)	0.0004 (16)	0.0027 (15)	−0.0060 (16)
C10	0.046 (2)	0.091 (4)	0.044 (2)	0.000 (2)	0.0122 (19)	−0.019 (2)
C11	0.052 (3)	0.079 (3)	0.060 (3)	0.013 (2)	0.004 (2)	−0.038 (2)
C12	0.046 (2)	0.050 (2)	0.059 (2)	0.0124 (18)	−0.0039 (19)	−0.0237 (19)
C13	0.081 (3)	0.044 (3)	0.095 (4)	0.023 (2)	−0.004 (3)	−0.034 (3)
C14	0.106 (4)	0.025 (2)	0.107 (4)	0.009 (2)	−0.004 (3)	−0.014 (2)
C15	0.068 (3)	0.0264 (18)	0.074 (3)	0.0044 (18)	−0.007 (2)	0.0001 (18)
C16	0.105 (4)	0.032 (2)	0.085 (3)	−0.009 (2)	0.002 (3)	0.019 (2)
C17	0.099 (4)	0.050 (3)	0.061 (3)	−0.013 (3)	0.011 (3)	0.020 (2)
C18	0.070 (3)	0.037 (2)	0.045 (2)	−0.0027 (18)	0.013 (2)	0.0070 (16)
C19	0.042 (2)	0.0239 (16)	0.0462 (19)	0.0049 (14)	−0.0069 (16)	−0.0018 (14)

Geometric parameters (Å, º) top

Zn1—O5ⁱ	2.065 (2)	C2—C3	1.392 (4)
Zn1—O2W	2.083 (3)	C3—C4	1.378 (4)
Zn1—N1	2.127 (2)	C3—H3	0.9300
Zn1—N2	2.137 (3)	C4—C5	1.395 (4)
Zn1—O1W	2.139 (2)	C4—H4A	0.9300
Zn1—O1	2.161 (2)	C5—C6	1.392 (4)
S1—O3	1.442 (3)	C5—C7	1.491 (4)
S1—O1	1.456 (2)	C6—H6	0.9300
S1—O2	1.461 (2)	C8—C12	1.407 (4)
S1—C1	1.776 (3)	C8—C19	1.431 (5)
O4—C2	1.344 (3)	C9—C10	1.401 (5)
O4—H4	0.839 (10)	C9—H9	0.9300
O5—C7	1.276 (3)	C10—C11	1.354 (6)
O5—Zn1ⁱⁱ	2.065 (2)	C10—H10	0.9300
O6—C7	1.249 (4)	C11—C12	1.405 (6)
O1W—H11	0.844 (10)	C11—H11A	0.9300
O1W—H12	0.839 (10)	C12—C13	1.427 (6)
O2W—H21	0.835 (10)	C13—C14	1.335 (6)
O2W—H22	0.836 (10)	C13—H13	0.9300
O3W—H31	0.839 (10)	C14—C15	1.429 (6)
O4W—H41	0.836 (10)	C14—H14	0.9300
O4W—H42	0.838 (10)	C15—C16	1.401 (6)
N1—C9	1.327 (4)	C15—C19	1.404 (5)
N1—C8	1.357 (4)	C16—C17	1.356 (6)
N2—C18	1.327 (4)	C16—H16	0.9300
N2—C19	1.362 (4)	C17—C18	1.398 (5)
C1—C6	1.383 (4)	C17—H17	0.9300
C1—C2	1.398 (4)	C18—H18	0.9300

O5ⁱ—Zn1—O2W	90.42 (11)	C3—C4—H4A	119.5
O5ⁱ—Zn1—N1	94.52 (9)	C5—C4—H4A	119.5
O2W—Zn1—N1	90.76 (10)	C6—C5—C4	118.2 (3)
O5ⁱ—Zn1—N2	171.77 (9)	C6—C5—C7	120.2 (3)
O2W—Zn1—N2	94.24 (12)	C4—C5—C7	121.6 (3)
N1—Zn1—N2	78.66 (10)	C1—C6—C5	121.0 (3)
O5ⁱ—Zn1—O1W	92.44 (8)	C1—C6—H6	119.5
O2W—Zn1—O1W	83.65 (9)	C5—C6—H6	119.5
N1—Zn1—O1W	171.10 (10)	O6—C7—O5	124.7 (3)
N2—Zn1—O1W	94.81 (9)	O6—C7—C5	117.8 (3)
O5ⁱ—Zn1—O1	86.06 (8)	O5—C7—C5	117.6 (3)
O2W—Zn1—O1	172.29 (10)	N1—C8—C12	122.4 (3)
N1—Zn1—O1	96.35 (9)	N1—C8—C19	117.9 (3)
N2—Zn1—O1	90.09 (10)	C12—C8—C19	119.6 (3)
O1W—Zn1—O1	89.65 (8)	N1—C9—C10	122.3 (4)
O3—S1—O1	111.69 (15)	N1—C9—H9	118.9
O3—S1—O2	113.39 (16)	C10—C9—H9	118.9
O1—S1—O2	111.59 (14)	C11—C10—C9	119.2 (4)
O3—S1—C1	108.07 (14)	C11—C10—H10	120.4
O1—S1—C1	106.63 (13)	C9—C10—H10	120.4
O2—S1—C1	104.94 (13)	C10—C11—C12	120.5 (3)
S1—O1—Zn1	150.55 (14)	C10—C11—H11A	119.8
C2—O4—H4	108 (3)	C12—C11—H11A	119.8
C7—O5—Zn1ⁱⁱ	125.22 (19)	C11—C12—C8	116.8 (4)
Zn1—O1W—H11	94 (3)	C11—C12—C13	124.3 (4)
Zn1—O1W—H12	118 (3)	C8—C12—C13	118.9 (4)
H11—O1W—H12	111 (4)	C14—C13—C12	121.2 (4)
Zn1—O2W—H21	128 (3)	C14—C13—H13	119.4
Zn1—O2W—H22	127 (3)	C12—C13—H13	119.4
H21—O2W—H22	105 (4)	C13—C14—C15	121.8 (4)
H41—O4W—H42	103 (4)	C13—C14—H14	119.1
C9—N1—C8	118.8 (3)	C15—C14—H14	119.1
C9—N1—Zn1	128.2 (2)	C16—C15—C19	117.4 (4)
C8—N1—Zn1	113.01 (19)	C16—C15—C14	124.2 (4)
C18—N2—C19	118.4 (3)	C19—C15—C14	118.5 (4)
C18—N2—Zn1	129.1 (2)	C17—C16—C15	120.3 (4)
C19—N2—Zn1	112.6 (2)	C17—C16—H16	119.8
C6—C1—C2	120.4 (3)	C15—C16—H16	119.8
C6—C1—S1	119.9 (2)	C16—C17—C18	118.9 (4)
C2—C1—S1	119.7 (2)	C16—C17—H17	120.5
O4—C2—C3	122.2 (3)	C18—C17—H17	120.5
O4—C2—C1	119.3 (3)	N2—C18—C17	122.8 (4)
C3—C2—C1	118.6 (3)	N2—C18—H18	118.6
C4—C3—C2	120.8 (3)	C17—C18—H18	118.6
C4—C3—H3	119.6	N2—C19—C15	122.2 (3)
C2—C3—H3	119.6	N2—C19—C8	117.9 (3)
C3—C4—C5	121.0 (3)	C15—C19—C8	120.0 (3)

O3—S1—O1—Zn1	173.2 (2)	Zn1ⁱⁱ—O5—C7—C5	−168.2 (2)
O2—S1—O1—Zn1	−58.7 (3)	C6—C5—C7—O6	13.8 (5)
C1—S1—O1—Zn1	55.4 (3)	C4—C5—C7—O6	−164.3 (3)
O5ⁱ—Zn1—O1—S1	179.0 (3)	C6—C5—C7—O5	−166.3 (3)
N1—Zn1—O1—S1	−86.9 (3)	C4—C5—C7—O5	15.7 (5)
N2—Zn1—O1—S1	−8.3 (3)	C9—N1—C8—C12	−0.9 (5)
O1W—Zn1—O1—S1	86.5 (3)	Zn1—N1—C8—C12	179.4 (3)
O5ⁱ—Zn1—N1—C9	−4.3 (3)	C9—N1—C8—C19	179.6 (3)
O2W—Zn1—N1—C9	86.1 (3)	Zn1—N1—C8—C19	−0.1 (4)
N2—Zn1—N1—C9	−179.7 (3)	C8—N1—C9—C10	−0.2 (5)
O1—Zn1—N1—C9	−90.9 (3)	Zn1—N1—C9—C10	179.5 (3)
O5ⁱ—Zn1—N1—C8	175.4 (2)	N1—C9—C10—C11	0.8 (6)
O2W—Zn1—N1—C8	−94.2 (2)	C9—C10—C11—C12	−0.4 (6)
N2—Zn1—N1—C8	0.0 (2)	C10—C11—C12—C8	−0.6 (6)
O1—Zn1—N1—C8	88.8 (2)	C10—C11—C12—C13	−178.7 (4)
O2W—Zn1—N2—C18	−91.4 (3)	N1—C8—C12—C11	1.2 (5)
N1—Zn1—N2—C18	178.7 (3)	C19—C8—C12—C11	−179.2 (3)
O1W—Zn1—N2—C18	−7.4 (3)	N1—C8—C12—C13	179.5 (4)
O1—Zn1—N2—C18	82.3 (3)	C19—C8—C12—C13	−1.0 (5)
O2W—Zn1—N2—C19	90.1 (2)	C11—C12—C13—C14	178.5 (5)
N1—Zn1—N2—C19	0.1 (2)	C8—C12—C13—C14	0.4 (7)
O1W—Zn1—N2—C19	174.0 (2)	C12—C13—C14—C15	−0.2 (8)
O1—Zn1—N2—C19	−96.3 (2)	C13—C14—C15—C16	−179.0 (5)
O3—S1—C1—C6	120.0 (3)	C13—C14—C15—C19	0.6 (7)
O1—S1—C1—C6	−119.8 (3)	C19—C15—C16—C17	0.4 (7)
O2—S1—C1—C6	−1.3 (3)	C14—C15—C16—C17	180.0 (5)
O3—S1—C1—C2	−60.3 (3)	C15—C16—C17—C18	0.5 (8)
O1—S1—C1—C2	59.9 (3)	C19—N2—C18—C17	0.7 (6)
O2—S1—C1—C2	178.4 (3)	Zn1—N2—C18—C17	−177.8 (3)
C6—C1—C2—O4	−179.0 (3)	C16—C17—C18—N2	−1.1 (7)
S1—C1—C2—O4	1.3 (4)	C18—N2—C19—C15	0.3 (5)
C6—C1—C2—C3	0.8 (5)	Zn1—N2—C19—C15	179.1 (3)
S1—C1—C2—C3	−178.9 (3)	C18—N2—C19—C8	−179.0 (3)
O4—C2—C3—C4	178.6 (3)	Zn1—N2—C19—C8	−0.2 (4)
C1—C2—C3—C4	−1.3 (5)	C16—C15—C19—N2	−0.8 (6)
C2—C3—C4—C5	0.4 (6)	C14—C15—C19—N2	179.5 (4)
C3—C4—C5—C6	0.8 (5)	C16—C15—C19—C8	178.5 (4)
C3—C4—C5—C7	178.9 (3)	C14—C15—C19—C8	−1.2 (6)
C2—C1—C6—C5	0.4 (5)	N1—C8—C19—N2	0.3 (5)
S1—C1—C6—C5	−179.8 (3)	C12—C8—C19—N2	−179.3 (3)
C4—C5—C6—C1	−1.2 (5)	N1—C8—C19—C15	−179.1 (3)
C7—C5—C6—C1	−179.4 (3)	C12—C8—C19—C15	1.4 (5)
Zn1ⁱⁱ—O5—C7—O6	11.8 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O4w	0.84 (1)	1.78 (1)	2.615 (3)	172 (4)
O1w—H11···O6ⁱ	0.84 (1)	1.68 (1)	2.520 (3)	172 (5)
O1w—H12···O3w	0.84 (1)	1.98 (2)	2.793 (2)	164 (4)
O2w—H21···O2ⁱⁱⁱ	0.84 (1)	1.94 (1)	2.760 (3)	166 (4)
O2w—H22···O1w^iv	0.84 (1)	1.93 (1)	2.767 (3)	174 (4)
O3w—H31···O2	0.84 (1)	1.95 (2)	2.752 (3)	160 (4)
O4w—H41···O4^v	0.84 (1)	2.23 (3)	2.939 (3)	142 (4)
O4w—H42···O5^vi	0.84 (1)	1.95 (1)	2.789 (3)	177 (4)

Symmetry codes: (i) x−1/2, y−1/2, z; (iii) x−1, y, z; (iv) −x+1, y, −z+1/2; (v) −x+3/2, −y+1/2, −z+1; (vi) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Zn(C₇H₄O₆S)(C₁₂H₈N₂)(H₂O)₂]·1.5H₂O
M_r	524.79
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	8.3682 (3), 17.3251 (6), 28.6686 (10)
β (°)	92.848 (1)
V (Å³)	4151.2 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.34
Crystal size (mm)	0.19 × 0.15 × 0.11

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.784, 0.866
No. of measured, independent and observed [I > 2σ(I)] reflections	20011, 4741, 3098
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.104, 1.16
No. of reflections	4741
No. of parameters	326
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.88

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O4w	0.84 (1)	1.78 (1)	2.615 (3)	172 (4)
O1w—H11···O6ⁱ	0.84 (1)	1.68 (1)	2.520 (3)	172 (5)
O1w—H12···O3w	0.84 (1)	1.98 (2)	2.793 (2)	164 (4)
O2w—H21···O2ⁱⁱ	0.84 (1)	1.94 (1)	2.760 (3)	166 (4)
O2w—H22···O1wⁱⁱⁱ	0.84 (1)	1.93 (1)	2.767 (3)	174 (4)
O3w—H31···O2	0.84 (1)	1.95 (2)	2.752 (3)	160 (4)
O4w—H41···O4^iv	0.84 (1)	2.23 (3)	2.939 (3)	142 (4)
O4w—H42···O5^v	0.84 (1)	1.95 (1)	2.789 (3)	177 (4)

Symmetry codes: (i) x−1/2, y−1/2, z; (ii) x−1, y, z; (iii) −x+1, y, −z+1/2; (iv) −x+3/2, −y+1/2, −z+1; (v) −x+2, −y+1, −z+1.

Acknowledgements

This work was supported by the Key Project of the Natural Science Foundation of Heilongjiang Province (No. ZD200903), the Key Project of the Education Bureau of Heilongjiang Province (Nos. 12511z023 and 2011CJHB006), the Innovation Team of the Education Bureau of Heilongjiang Province (No. 2010 t d03), Heilongjiang University (Hdtd2010–04) and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12).

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Fang, X.-Q., Chen, P.-G., Zhu, Z.-B., Deng, Z.-P. & Gao, S. (2011). Chin. J. Inorg. Chem. 27, 1733–1737. CAS Google Scholar
Fang, X.-Q., Gao, S. & Ng, S. W. (2012). Acta Cryst. E68, m721. CSD CrossRef IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.