[N′-(5-Chloro-2-oxidobenzyl-κO)-2,4-dihy­droxy­benzohydrazidato-κ2N′,O](methanol-κO)dioxidomolybdenum(VI)–4,4′-bipyridine (1/1)

Ngan, N.K.; Wong, R.C.S.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536811017259

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page m747

doi:10.1107/S1600536811017259

Open

access

[N′-(5-Chloro-2-oxidobenzyl-κO)-2,4-dihydroxybenzohydrazidato-κ²N′,O](methanol-κO)dioxidomolybdenum(VI)–4,4′-bipyridine (1/1)

Ngui Khiong Ngan,^a Richard Chee Seng Wong,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 5 May 2011; accepted 7 May 2011; online 14 May 2011)

In the title co-crystal, [Mo(C₁₄H₉ClN₂O₄)O₂(CH₃OH)]·C₁₀H₈N₂, the deprotonated Schiff base O,N,O′-chelates to the Mo^VI atom, the three atoms involved in chelation comprising the fac sites of the octahedron surrounding the methanol-coordinated metal atom. The methanol molecule forms an O—H⋯N hydrogen bond to an N atom of the 4,4′-bipyridine solvent molecule; the hydroxy group of the Schiff base forms an O—H⋯N hydrogen bond to the other N atom of another molecule. The two hydrogen bonds leading to the formation of a helical chain running along the b axis.

Related literature

For a related Mo^VIO₂–4′,4-bipyridine adduct, see: Dinda et al. (2006 ). For the structure of the unsubstituted Schiff base, see: Pan & Yang (2005 ).

Experimental

Crystal data

[Mo(C₁₄H₉ClN₂O₄)O₂(CH₄O)]·C₁₀H₈N₂
M_r = 620.85
Monoclinic, P 2₁ /n
a = 6.9575 (3) Å
b = 7.4541 (4) Å
c = 47.197 (2) Å
β = 92.0073 (6)°
V = 2446.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.70 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.885, T_max = 1.000
29717 measured reflections
5604 independent reflections
5408 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.138
S = 1.23
5604 reflections
356 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.55 e Å⁻³
Δρ_min = −1.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.84 (1)	1.85 (3)	2.600 (4)	147 (6)
O3—H3⋯N3	0.84 (1)	1.92 (2)	2.741 (5)	166 (6)
O7—H7⋯N4ⁱ	0.84 (1)	1.84 (1)	2.679 (4)	175 (6)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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/S1600536811017259/jh2289sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017259/jh2289Isup2.hkl

checkCIF report

Comment top

The Schiff bases that are synthesized by condensing salicylaldehyde (and its substituted analogs) with benzohydrazide (and its substituted analogs) function as terdentate O,N,O'-chelates to a wide range of metal ions. A large number of metal derivatives have been reported; in octahedral systems, the ligand generally exists as a doubly-deprotonated species that chelates in a fac manner. The crystal structure of the parent (unsubstituted) ligand has been reported (Pan & Yang, 2005); a dioxomolybdenum(VI) derivative is known in which 4,4'-bipyridine binds to two metal atoms (Dinda et al., 2006). In the present study, using a Schiff base that possesses substitutents leads to a solvent-coordinated derivative in which 4,4'-bipyridine interacts indirectly, through the solvent molecule, in an outer-sphere coordination mode. In the co-crystal, MoO₂(CH₃OH)(C₁₄H₉ClN₂O₄^).C₁₀H₈N₂(Scheme I), the deprotonated Schiff base O,N,O'-chelates to the Mo^VI atom, the three atoms involved in chelation comprising the fac sites of the octahedron surrounding the methanol-coordinated metal center (Fig. 1). The solvent molecule forms an O–H···N hydrogen bond to a N atom of the 4,4'-bipyridine molecule; the hydroxy group forms an O–H···N hydrogen bond to the other N atom of another molecule, the two hydrogen bonds leading to the formation of a helical chain that runs along the b-axis of the monoclinic unit cell (Table 1).

Related literature top

For a related Mo^VIO₂–4',4-bipyridine adduct, see: Dinda et al. (2006). For the structure of the unsubstituted Schiff base, see: Pan & Yang (2005).

Experimental top

3-Ethoxysalicylaldehyde (0.166 g, 1 mmol) and 2,4-dihydroxybenzohydrazide (0.156 g, 1 mmol) were condensed in methanol (100 ml). The solution was heated to give a yellow coloration. The cool solution yielded the desired Schiff base as a yellow compound. The ligand (0.306 g, 1 mmol) and di(acetylacetonato)dioxomolybdenum(VI) (0.328 g, 1 mmol) were dissolved in heated in methanol for an hour. To the orange-red solution was added 4,4'-bipyridine (0.08 g, 0.5 mmol); heating was continued for another hour. The solution was filtered and set aside for the growth of crystals, m.p. 533–535 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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. Thermal ellipsoid plot (Barbour, 2001) of MoO₂(CH₃OH)(C₁₄H₉ClN₂O₄^).C₁₀H₈N₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

[N'-(5-Chloro-2-oxidobenzyl-κO)-2,4-dihydroxybenzohydrazidato- κ²N',O](methanol-κO)dioxidomolybdenum(VI)–4,4'- bipyridine (1/1) top

Crystal data top

[Mo(C₁₄H₉ClN₂O₄)O₂(CH₄O)]·C₁₀H₈N₂	F(000) = 1256
M_r = 620.85	D_x = 1.686 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9874 reflections
a = 6.9575 (3) Å	θ = 2.6–28.2°
b = 7.4541 (4) Å	µ = 0.70 mm⁻¹
c = 47.197 (2) Å	T = 100 K
β = 92.0073 (6)°	Prism, orange–red
V = 2446.2 (2) Å³	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	5604 independent reflections
Radiation source: fine-focus sealed tube	5408 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 27.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.885, T_max = 1.000	k = −9→9
29717 measured reflections	l = −61→61

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.23	w = 1/[σ²(F_o²) + (0.058P)² + 9.6979P] where P = (F_o² + 2F_c²)/3
5604 reflections	(Δ/σ)_max = 0.001
356 parameters	Δρ_max = 0.55 e Å⁻³
3 restraints	Δρ_min = −1.25 e Å⁻³

Crystal data top

[Mo(C₁₄H₉ClN₂O₄)O₂(CH₄O)]·C₁₀H₈N₂	V = 2446.2 (2) Å³
M_r = 620.85	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.9575 (3) Å	µ = 0.70 mm⁻¹
b = 7.4541 (4) Å	T = 100 K
c = 47.197 (2) Å	0.25 × 0.20 × 0.20 mm
β = 92.0073 (6)°

Data collection top

Bruker SMART APEX diffractometer	5604 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5408 reflections with I > 2σ(I)
T_min = 0.885, T_max = 1.000	R_int = 0.032
29717 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	3 restraints
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.23	Δρ_max = 0.55 e Å⁻³
5604 reflections	Δρ_min = −1.25 e Å⁻³
356 parameters

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

	x	y	z	U_iso*/U_eq
Mo1	1.01769 (4)	0.07720 (4)	0.416314 (7)	0.01254 (11)
Cl1	0.25401 (13)	−0.34030 (13)	0.50086 (2)	0.0185 (2)
O1	0.9736 (4)	0.1896 (4)	0.37790 (6)	0.0160 (5)
O2	0.4441 (4)	0.1634 (4)	0.33108 (6)	0.0213 (6)
H2	0.471 (8)	0.126 (8)	0.3475 (6)	0.040 (17)*
O3	0.7322 (5)	0.4673 (5)	0.25549 (6)	0.0303 (8)
H3	0.624 (4)	0.454 (8)	0.2474 (11)	0.031 (15)*
O4	0.9260 (4)	0.0010 (4)	0.45224 (6)	0.0156 (5)
O5	1.2262 (4)	0.1843 (4)	0.42621 (6)	0.0173 (6)
O6	1.0877 (4)	−0.1250 (4)	0.40328 (6)	0.0191 (6)
O7	0.8759 (4)	0.3422 (4)	0.42838 (6)	0.0161 (5)
H7	0.804 (6)	0.394 (7)	0.4163 (9)	0.029 (14)*
N1	0.6590 (5)	0.0904 (4)	0.37578 (7)	0.0149 (6)
N2	0.7088 (5)	0.0358 (4)	0.40308 (6)	0.0126 (6)
N3	0.4092 (5)	0.3848 (5)	0.22321 (7)	0.0218 (7)
N4	−0.1397 (5)	0.0211 (5)	0.10765 (7)	0.0187 (7)
C1	0.7832 (6)	0.2412 (5)	0.33577 (8)	0.0151 (7)
C2	0.9404 (6)	0.3226 (5)	0.32289 (8)	0.0177 (8)
H2A	1.0618	0.3255	0.3327	0.021*
C3	0.9220 (7)	0.3981 (6)	0.29631 (9)	0.0232 (9)
H3A	1.0287	0.4556	0.2882	0.028*
C4	0.7447 (6)	0.3896 (6)	0.28138 (8)	0.0215 (8)
C5	0.5880 (6)	0.3080 (6)	0.29358 (9)	0.0221 (8)
H5	0.4681	0.3025	0.2834	0.027*
C6	0.6056 (6)	0.2349 (5)	0.32048 (8)	0.0166 (7)
C7	0.8056 (5)	0.1687 (5)	0.36418 (8)	0.0139 (7)
C8	0.5761 (5)	−0.0460 (5)	0.41652 (8)	0.0139 (7)
H8	0.4564	−0.0673	0.4068	0.017*
C9	0.5994 (5)	−0.1073 (5)	0.44556 (8)	0.0127 (7)
C10	0.4417 (5)	−0.1914 (5)	0.45779 (8)	0.0151 (7)
H10	0.3276	−0.2131	0.4467	0.018*
C11	0.4521 (5)	−0.2421 (5)	0.48572 (8)	0.0144 (7)
C12	0.6185 (6)	−0.2137 (5)	0.50248 (8)	0.0155 (7)
H12	0.6237	−0.2496	0.5218	0.019*
C13	0.7755 (5)	−0.1333 (5)	0.49074 (8)	0.0129 (7)
H13	0.8895	−0.1148	0.5020	0.015*
C14	0.7686 (5)	−0.0786 (5)	0.46234 (8)	0.0138 (7)
C15	0.9788 (6)	0.4819 (6)	0.44335 (9)	0.0217 (8)
H15A	0.8873	0.5691	0.4506	0.033*
H15B	1.0655	0.5420	0.4305	0.033*
H15C	1.0541	0.4298	0.4593	0.033*
C16	0.4737 (6)	0.3877 (5)	0.19684 (8)	0.0183 (8)
H16	0.5972	0.4377	0.1940	0.022*
C17	0.3700 (6)	0.3215 (5)	0.17342 (8)	0.0172 (8)
H17	0.4216	0.3272	0.1551	0.021*
C18	0.1891 (6)	0.2466 (5)	0.17723 (9)	0.0179 (8)
C19	0.1193 (6)	0.2480 (6)	0.20453 (9)	0.0233 (9)
H19	−0.0055	0.2029	0.2080	0.028*
C20	0.2334 (7)	0.3156 (7)	0.22641 (9)	0.0284 (10)
H20	0.1846	0.3131	0.2450	0.034*
C21	0.0510 (6)	0.0001 (6)	0.10986 (8)	0.0190 (8)
H21	0.1123	−0.0677	0.0957	0.023*
C22	0.1631 (6)	0.0724 (6)	0.13174 (9)	0.0190 (8)
H22	0.2986	0.0558	0.1323	0.023*
C23	0.0753 (6)	0.1701 (5)	0.15298 (8)	0.0165 (7)
C24	−0.1230 (6)	0.1915 (5)	0.15073 (9)	0.0180 (8)
H24	−0.1887	0.2568	0.1647	0.022*
C25	−0.2235 (6)	0.1164 (6)	0.12788 (9)	0.0206 (8)
H25	−0.3588	0.1332	0.1265	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mo1	0.01129 (17)	0.01290 (17)	0.01333 (17)	−0.00009 (11)	−0.00088 (11)	−0.00010 (12)
Cl1	0.0184 (4)	0.0176 (4)	0.0195 (4)	−0.0031 (3)	0.0036 (3)	0.0016 (4)
O1	0.0144 (12)	0.0193 (14)	0.0140 (13)	−0.0022 (10)	−0.0008 (10)	−0.0006 (11)
O2	0.0198 (14)	0.0291 (16)	0.0146 (14)	−0.0070 (12)	−0.0038 (11)	0.0040 (12)
O3	0.0366 (19)	0.042 (2)	0.0120 (14)	−0.0127 (16)	−0.0049 (13)	0.0059 (13)
O4	0.0149 (13)	0.0187 (14)	0.0130 (13)	−0.0028 (11)	−0.0029 (10)	0.0006 (11)
O5	0.0146 (13)	0.0192 (14)	0.0180 (13)	−0.0004 (11)	−0.0019 (10)	−0.0001 (11)
O6	0.0203 (14)	0.0187 (14)	0.0180 (14)	0.0025 (11)	−0.0017 (11)	−0.0023 (11)
O7	0.0202 (13)	0.0136 (13)	0.0140 (13)	0.0003 (11)	−0.0051 (10)	−0.0021 (10)
N1	0.0161 (15)	0.0154 (15)	0.0130 (15)	−0.0002 (12)	−0.0021 (12)	0.0018 (12)
N2	0.0162 (15)	0.0121 (14)	0.0093 (14)	0.0011 (12)	−0.0020 (11)	−0.0004 (11)
N3	0.0302 (19)	0.0229 (18)	0.0120 (16)	−0.0037 (15)	−0.0024 (14)	0.0007 (13)
N4	0.0209 (17)	0.0145 (16)	0.0205 (17)	−0.0039 (13)	−0.0019 (13)	0.0045 (13)
C1	0.0200 (18)	0.0128 (17)	0.0124 (17)	0.0009 (14)	−0.0010 (14)	−0.0027 (14)
C2	0.0204 (19)	0.0190 (19)	0.0136 (17)	−0.0053 (15)	0.0009 (14)	−0.0029 (15)
C3	0.028 (2)	0.025 (2)	0.0172 (19)	−0.0073 (17)	0.0025 (16)	−0.0024 (16)
C4	0.031 (2)	0.021 (2)	0.0124 (18)	−0.0050 (17)	0.0000 (16)	−0.0015 (15)
C5	0.024 (2)	0.026 (2)	0.0166 (19)	−0.0048 (17)	−0.0056 (15)	−0.0001 (16)
C6	0.0203 (19)	0.0148 (18)	0.0147 (17)	−0.0028 (14)	−0.0001 (14)	−0.0012 (14)
C7	0.0163 (17)	0.0133 (17)	0.0118 (16)	0.0011 (14)	−0.0015 (13)	−0.0050 (14)
C8	0.0127 (16)	0.0124 (17)	0.0165 (17)	−0.0002 (13)	−0.0013 (13)	−0.0011 (14)
C9	0.0159 (17)	0.0097 (16)	0.0124 (16)	0.0018 (13)	−0.0009 (13)	−0.0001 (13)
C10	0.0161 (17)	0.0112 (17)	0.0180 (18)	0.0014 (14)	−0.0001 (14)	−0.0014 (14)
C11	0.0159 (17)	0.0088 (16)	0.0186 (18)	−0.0005 (13)	0.0042 (14)	−0.0020 (14)
C12	0.0208 (19)	0.0085 (16)	0.0173 (18)	0.0023 (14)	−0.0007 (14)	0.0015 (14)
C13	0.0186 (17)	0.0103 (16)	0.0095 (16)	−0.0003 (14)	−0.0023 (13)	0.0020 (13)
C14	0.0170 (17)	0.0101 (16)	0.0143 (17)	0.0021 (14)	−0.0007 (14)	−0.0014 (14)
C15	0.025 (2)	0.0143 (18)	0.026 (2)	−0.0030 (16)	−0.0001 (16)	−0.0046 (16)
C16	0.024 (2)	0.0153 (18)	0.0159 (18)	−0.0008 (15)	−0.0006 (15)	0.0027 (15)
C17	0.0210 (19)	0.0188 (19)	0.0117 (17)	0.0020 (15)	0.0003 (14)	0.0018 (14)
C18	0.0179 (18)	0.0168 (18)	0.0191 (19)	0.0035 (15)	0.0008 (15)	−0.0021 (15)
C19	0.022 (2)	0.028 (2)	0.020 (2)	−0.0039 (17)	0.0056 (16)	0.0006 (17)
C20	0.034 (2)	0.037 (3)	0.0143 (19)	−0.006 (2)	0.0050 (17)	−0.0007 (18)
C21	0.024 (2)	0.0170 (19)	0.0164 (18)	0.0022 (16)	0.0019 (15)	−0.0018 (15)
C22	0.0150 (18)	0.0189 (19)	0.023 (2)	0.0009 (15)	0.0020 (15)	−0.0001 (16)
C23	0.0168 (18)	0.0149 (18)	0.0176 (18)	0.0025 (14)	−0.0016 (14)	0.0056 (15)
C24	0.0163 (18)	0.0144 (18)	0.024 (2)	0.0023 (14)	0.0044 (15)	0.0022 (15)
C25	0.0135 (18)	0.020 (2)	0.028 (2)	0.0010 (15)	−0.0011 (15)	0.0030 (17)

Geometric parameters (Å, º) top

Mo1—O6	1.705 (3)	C8—C9	1.448 (5)
Mo1—O5	1.707 (3)	C8—H8	0.9500
Mo1—O4	1.918 (3)	C9—C10	1.405 (5)
Mo1—O1	2.011 (3)	C9—C14	1.412 (5)
Mo1—N2	2.238 (3)	C10—C11	1.370 (5)
Mo1—O7	2.289 (3)	C10—H10	0.9500
Cl1—C11	1.737 (4)	C11—C12	1.395 (5)
O1—C7	1.326 (5)	C12—C13	1.379 (5)
O2—C6	1.355 (5)	C12—H12	0.9500
O2—H2	0.840 (10)	C13—C14	1.400 (5)
O3—C4	1.352 (5)	C13—H13	0.9500
O3—H3	0.840 (10)	C15—H15A	0.9800
O4—C14	1.347 (5)	C15—H15B	0.9800
O7—C15	1.436 (5)	C15—H15C	0.9800
O7—H7	0.838 (10)	C16—C17	1.389 (6)
N1—C7	1.311 (5)	C16—H16	0.9500
N1—N2	1.384 (4)	C17—C18	1.394 (6)
N2—C8	1.292 (5)	C17—H17	0.9500
N3—C16	1.338 (5)	C18—C19	1.393 (6)
N3—C20	1.341 (6)	C18—C23	1.483 (6)
N4—C21	1.337 (5)	C19—C20	1.376 (6)
N4—C25	1.340 (6)	C19—H19	0.9500
C1—C2	1.408 (5)	C20—H20	0.9500
C1—C6	1.410 (5)	C21—C22	1.382 (6)
C1—C7	1.449 (5)	C21—H21	0.9500
C2—C3	1.377 (6)	C22—C23	1.397 (6)
C2—H2A	0.9500	C22—H22	0.9500
C3—C4	1.401 (6)	C23—C24	1.389 (5)
C3—H3A	0.9500	C24—C25	1.383 (6)
C4—C5	1.390 (6)	C24—H24	0.9500
C5—C6	1.383 (6)	C25—H25	0.9500
C5—H5	0.9500

O6—Mo1—O5	105.14 (14)	C10—C9—C8	117.8 (3)
O6—Mo1—O4	99.50 (13)	C14—C9—C8	123.1 (3)
O5—Mo1—O4	101.67 (12)	C11—C10—C9	120.2 (4)
O6—Mo1—O1	94.56 (13)	C11—C10—H10	119.9
O5—Mo1—O1	98.81 (12)	C9—C10—H10	119.9
O4—Mo1—O1	151.09 (11)	C10—C11—C12	121.2 (4)
O6—Mo1—N2	93.51 (13)	C10—C11—Cl1	119.7 (3)
O5—Mo1—N2	159.97 (13)	C12—C11—Cl1	119.0 (3)
O4—Mo1—N2	81.96 (11)	C13—C12—C11	119.4 (4)
O1—Mo1—N2	72.03 (11)	C13—C12—H12	120.3
O6—Mo1—O7	169.60 (12)	C11—C12—H12	120.3
O5—Mo1—O7	84.14 (12)	C12—C13—C14	120.7 (3)
O4—Mo1—O7	82.88 (11)	C12—C13—H13	119.7
O1—Mo1—O7	79.14 (11)	C14—C13—H13	119.7
N2—Mo1—O7	76.73 (11)	O4—C14—C13	117.8 (3)
C7—O1—Mo1	119.7 (2)	O4—C14—C9	122.7 (3)
C6—O2—H2	108 (4)	C13—C14—C9	119.5 (3)
C4—O3—H3	113 (4)	O7—C15—H15A	109.5
C14—O4—Mo1	138.0 (2)	O7—C15—H15B	109.5
C15—O7—Mo1	122.4 (2)	H15A—C15—H15B	109.5
C15—O7—H7	106 (4)	O7—C15—H15C	109.5
Mo1—O7—H7	119 (4)	H15A—C15—H15C	109.5
C7—N1—N2	110.3 (3)	H15B—C15—H15C	109.5
C8—N2—N1	115.9 (3)	N3—C16—C17	123.5 (4)
C8—N2—Mo1	128.6 (3)	N3—C16—H16	118.2
N1—N2—Mo1	115.2 (2)	C17—C16—H16	118.2
C16—N3—C20	116.6 (4)	C16—C17—C18	119.1 (4)
C21—N4—C25	117.5 (4)	C16—C17—H17	120.5
C2—C1—C6	118.3 (4)	C18—C17—H17	120.5
C2—C1—C7	120.0 (4)	C19—C18—C17	117.5 (4)
C6—C1—C7	121.7 (4)	C19—C18—C23	121.5 (4)
C3—C2—C1	121.4 (4)	C17—C18—C23	121.0 (4)
C3—C2—H2A	119.3	C20—C19—C18	119.1 (4)
C1—C2—H2A	119.3	C20—C19—H19	120.5
C2—C3—C4	119.5 (4)	C18—C19—H19	120.5
C2—C3—H3A	120.3	N3—C20—C19	124.1 (4)
C4—C3—H3A	120.3	N3—C20—H20	117.9
O3—C4—C5	122.3 (4)	C19—C20—H20	117.9
O3—C4—C3	117.6 (4)	N4—C21—C22	123.1 (4)
C5—C4—C3	120.1 (4)	N4—C21—H21	118.5
C6—C5—C4	120.5 (4)	C22—C21—H21	118.5
C6—C5—H5	119.8	C21—C22—C23	119.3 (4)
C4—C5—H5	119.8	C21—C22—H22	120.3
O2—C6—C5	116.5 (4)	C23—C22—H22	120.3
O2—C6—C1	123.2 (4)	C24—C23—C22	117.6 (4)
C5—C6—C1	120.3 (4)	C24—C23—C18	121.1 (4)
N1—C7—O1	122.3 (3)	C22—C23—C18	121.3 (4)
N1—C7—C1	119.5 (3)	C25—C24—C23	119.1 (4)
O1—C7—C1	118.2 (3)	C25—C24—H24	120.4
N2—C8—C9	123.7 (3)	C23—C24—H24	120.4
N2—C8—H8	118.1	N4—C25—C24	123.3 (4)
C9—C8—H8	118.1	N4—C25—H25	118.3
C10—C9—C14	119.0 (3)	C24—C25—H25	118.3

O6—Mo1—O1—C7	86.0 (3)	C2—C1—C7—N1	−178.8 (4)
O5—Mo1—O1—C7	−167.9 (3)	C6—C1—C7—N1	2.0 (6)
O4—Mo1—O1—C7	−33.2 (4)	C2—C1—C7—O1	3.3 (5)
N2—Mo1—O1—C7	−6.3 (3)	C6—C1—C7—O1	−175.8 (3)
O7—Mo1—O1—C7	−85.7 (3)	N1—N2—C8—C9	−177.8 (3)
O6—Mo1—O4—C14	−78.0 (4)	Mo1—N2—C8—C9	9.0 (5)
O5—Mo1—O4—C14	174.3 (4)	N2—C8—C9—C10	178.8 (4)
O1—Mo1—O4—C14	40.0 (5)	N2—C8—C9—C14	1.9 (6)
N2—Mo1—O4—C14	14.3 (4)	C14—C9—C10—C11	0.9 (5)
O7—Mo1—O4—C14	91.8 (4)	C8—C9—C10—C11	−176.1 (3)
O6—Mo1—O7—C15	−164.6 (6)	C9—C10—C11—C12	−0.7 (6)
O5—Mo1—O7—C15	−11.1 (3)	C9—C10—C11—Cl1	178.2 (3)
O4—Mo1—O7—C15	91.5 (3)	C10—C11—C12—C13	0.0 (6)
O1—Mo1—O7—C15	−111.2 (3)	Cl1—C11—C12—C13	−179.0 (3)
N2—Mo1—O7—C15	174.9 (3)	C11—C12—C13—C14	0.6 (6)
C7—N1—N2—C8	−178.9 (3)	Mo1—O4—C14—C13	170.9 (3)
C7—N1—N2—Mo1	−4.8 (4)	Mo1—O4—C14—C9	−9.5 (6)
O6—Mo1—N2—C8	85.6 (3)	C12—C13—C14—O4	179.3 (3)
O5—Mo1—N2—C8	−115.6 (4)	C12—C13—C14—C9	−0.4 (6)
O4—Mo1—N2—C8	−13.5 (3)	C10—C9—C14—O4	180.0 (3)
O1—Mo1—N2—C8	179.2 (4)	C8—C9—C14—O4	−3.2 (6)
O7—Mo1—N2—C8	−98.1 (3)	C10—C9—C14—C13	−0.3 (5)
O6—Mo1—N2—N1	−87.7 (3)	C8—C9—C14—C13	176.4 (3)
O5—Mo1—N2—N1	71.1 (4)	C20—N3—C16—C17	−0.9 (6)
O4—Mo1—N2—N1	173.2 (3)	N3—C16—C17—C18	−0.4 (6)
O1—Mo1—N2—N1	6.0 (2)	C16—C17—C18—C19	2.1 (6)
O7—Mo1—N2—N1	88.7 (2)	C16—C17—C18—C23	−178.4 (4)
C6—C1—C2—C3	1.4 (6)	C17—C18—C19—C20	−2.6 (6)
C7—C1—C2—C3	−177.8 (4)	C23—C18—C19—C20	178.0 (4)
C1—C2—C3—C4	−1.8 (6)	C16—N3—C20—C19	0.4 (7)
C2—C3—C4—O3	179.2 (4)	C18—C19—C20—N3	1.4 (8)
C2—C3—C4—C5	1.1 (7)	C25—N4—C21—C22	−0.3 (6)
O3—C4—C5—C6	−178.0 (4)	N4—C21—C22—C23	1.0 (6)
C3—C4—C5—C6	0.0 (7)	C21—C22—C23—C24	−0.8 (6)
C4—C5—C6—O2	177.9 (4)	C21—C22—C23—C18	178.6 (4)
C4—C5—C6—C1	−0.4 (6)	C19—C18—C23—C24	37.6 (6)
C2—C1—C6—O2	−178.5 (4)	C17—C18—C23—C24	−141.8 (4)
C7—C1—C6—O2	0.7 (6)	C19—C18—C23—C22	−141.7 (4)
C2—C1—C6—C5	−0.2 (6)	C17—C18—C23—C22	38.9 (6)
C7—C1—C6—C5	178.9 (4)	C22—C23—C24—C25	−0.1 (6)
N2—N1—C7—O1	−0.5 (5)	C18—C23—C24—C25	−179.4 (4)
N2—N1—C7—C1	−178.2 (3)	C21—N4—C25—C24	−0.6 (6)
Mo1—O1—C7—N1	6.3 (5)	C23—C24—C25—N4	0.8 (6)
Mo1—O1—C7—C1	−175.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.84 (1)	1.85 (3)	2.600 (4)	147 (6)
O3—H3···N3	0.84 (1)	1.92 (2)	2.741 (5)	166 (6)
O7—H7···N4ⁱ	0.84 (1)	1.84 (1)	2.679 (4)	175 (6)

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Mo(C₁₄H₉ClN₂O₄)O₂(CH₄O)]·C₁₀H₈N₂
M_r	620.85
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	6.9575 (3), 7.4541 (4), 47.197 (2)
β (°)	92.0073 (6)
V (Å³)	2446.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.885, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	29717, 5604, 5408
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.138, 1.23
No. of reflections	5604
No. of parameters	356
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.55, −1.25

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
O2—H2···N1	0.84 (1)	1.85 (3)	2.600 (4)	147 (6)
O3—H3···N3	0.84 (1)	1.92 (2)	2.741 (5)	166 (6)
O7—H7···N4ⁱ	0.84 (1)	1.84 (1)	2.679 (4)	175 (6)

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

We thank the University of Malaya (grant Nos. RG020/09AFR, PS378/2010B) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dinda, R., Ghosh, S., Falvello, L. R., Tomas, M. & Mak, T. C. W. (2006). Polyhedron, 25, 2375–2382. CSD CrossRef CAS Google Scholar
Pan, F.-Y. & Yang, J.-G. (2005). Z. Kristallogr. New Cryst. Struct. 220, 517–518. CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. 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.