Crystal structure of di-μ-hydroxido-bis­[aqua­(1,10-phenanthroline-κ²N,N′)copper(II)] naphthalene-2,6-di­carboxyl­ate hexa­hydrate

The cations and anions of the title compound are organized through π–π stacking between the aromatic rings of the 1,10-phenanthroline and the naphthalene-2,6-carboxyl­ate into a two-dimensional structure. The extensive O—H...H hydrogen bonds further connect the cations, anions and lattice water mol­ecules into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.037
• wR factor = 0.087
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         14 Note
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         36 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          1 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          9 Note

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

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

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Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS2012 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CIFTAB (Sheldrick, 2013).

Di-µ-hydroxido-bis[aqua(1,10-phenanthroline-κ²N,N')copper(II)] naphthalene-2,6-dicarboxylate hexahydrate

Crystal data

[Cu2(OH)2(C12H8N2)2(H2O)2](C12H6O4)·6H2O	F(000) = 908
Mr = 879.80	Dx = 1.611 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.3626 (16) Å	Cell parameters from 4729 reflections
b = 10.5812 (18) Å	θ = 2.2–27.5°
c = 18.648 (3) Å	µ = 1.25 mm^−1
β = 100.961 (3)°	T = 298 K
V = 1813.7 (5) Å^3	Prism-hexagonal, blue
Z = 2	0.32 × 0.14 × 0.13 mm

Data collection

Bruker SMART APEX CCD diffractometer	4168 independent reflections
Radiation source: fine-focus sealed tube	3164 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 8.333 pixels mm^-1	θmax = 27.6°, θmin = 2.2°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −13→13
Tmin = 0.691, Tmax = 0.858	l = −24→24
12102 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0327P)^2 + 0.9957P] where P = (Fo^2 + 2Fc^2)/3
4168 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 0.41 e Å^−3
36 restraints	Δρmin = −0.30 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
Cu1	0.36968 (3)	0.07336 (3)	0.50127 (2)	0.02290 (10)
O1	0.5472 (2)	0.60808 (19)	0.36776 (11)	0.0381 (5)
O2	0.6367 (2)	0.5229 (2)	0.27719 (11)	0.0495 (6)
O3	0.52734 (18)	−0.00259 (17)	0.57091 (9)	0.0261 (4)
H3A	0.571 (3)	0.047 (2)	0.5945 (15)	0.039*
O4	0.4830 (2)	0.26261 (19)	0.50689 (11)	0.0349 (5)
H4A	0.456 (4)	0.303 (3)	0.4734 (12)	0.052*
H4B	0.472 (4)	0.301 (3)	0.5401 (13)	0.052*
O5	0.3358 (3)	0.8164 (2)	0.31710 (13)	0.0498 (6)
H5A	0.387 (4)	0.760 (3)	0.319 (2)	0.075*
H5B	0.341 (4)	0.855 (3)	0.2833 (14)	0.075*
O6	0.3821 (3)	0.3788 (2)	0.37053 (15)	0.0525 (6)
H6A	0.414 (4)	0.4451 (19)	0.371 (2)	0.079*
H6B	0.428 (4)	0.333 (3)	0.352 (2)	0.079*
O7	0.5308 (3)	0.1767 (2)	0.32376 (12)	0.0459 (6)
H7A	0.519 (4)	0.135 (3)	0.3554 (15)	0.069*
H7B	0.491 (4)	0.140 (3)	0.2907 (14)	0.069*
C1	0.7904 (3)	0.5295 (2)	0.39346 (14)	0.0266 (6)
C2	0.9135 (3)	0.4941 (3)	0.36397 (14)	0.0306 (6)
H2	0.9045	0.4853	0.3137	0.037*
C3	1.0446 (3)	0.4728 (3)	0.40805 (14)	0.0304 (6)
H3	1.1242	0.4512	0.3874	0.036*
C4	0.9383 (3)	0.5169 (2)	0.51493 (14)	0.0255 (5)
C5	0.8052 (3)	0.5398 (2)	0.46729 (14)	0.0280 (6)
H5	0.7247	0.5627	0.4869	0.034*
C6	0.6480 (3)	0.5557 (3)	0.34251 (15)	0.0308 (6)
N7	0.1858 (2)	0.11609 (19)	0.43037 (11)	0.0232 (5)
C8	0.1602 (3)	0.1156 (3)	0.35799 (14)	0.0290 (6)
H8	0.2362	0.0970	0.3341	0.035*
C9	0.0233 (3)	0.1419 (3)	0.31650 (15)	0.0332 (6)
H9	0.0093	0.1403	0.2658	0.040*
C10	−0.0906 (3)	0.1702 (3)	0.35005 (15)	0.0320 (6)
H10	−0.1821	0.1876	0.3225	0.038*
C11	−0.1773 (3)	0.2011 (2)	0.46792 (16)	0.0314 (6)
H11	−0.2711	0.2198	0.4435	0.038*
C12	−0.1477 (3)	0.2013 (2)	0.54136 (15)	0.0304 (6)
H12	−0.2214	0.2205	0.5667	0.037*
C13	0.0330 (3)	0.1719 (3)	0.65763 (15)	0.0328 (6)
H13	−0.0365	0.1890	0.6859	0.039*
C14	0.1731 (3)	0.1457 (3)	0.69029 (15)	0.0341 (7)
H14	0.1999	0.1467	0.7409	0.041*
C15	0.2761 (3)	0.1174 (3)	0.64738 (14)	0.0290 (6)
H15	0.3708	0.0985	0.6704	0.035*
N16	0.2434 (2)	0.11657 (19)	0.57492 (11)	0.0230 (5)
C17	0.0737 (2)	0.1444 (2)	0.46436 (14)	0.0217 (5)
C18	−0.0673 (3)	0.1726 (2)	0.42647 (14)	0.0251 (5)
C19	0.1051 (2)	0.1448 (2)	0.54237 (13)	0.0215 (5)
C20	−0.0055 (3)	0.1728 (2)	0.58126 (14)	0.0256 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01878 (16)	0.02928 (18)	0.02090 (16)	0.00393 (13)	0.00440 (11)	0.00009 (14)
O1	0.0302 (10)	0.0441 (12)	0.0373 (11)	0.0069 (9)	−0.0002 (9)	−0.0061 (9)
O2	0.0487 (13)	0.0674 (16)	0.0277 (11)	0.0166 (12)	−0.0042 (10)	−0.0074 (11)
O3	0.0238 (9)	0.0330 (11)	0.0208 (9)	0.0057 (8)	0.0022 (7)	−0.0031 (8)
O4	0.0370 (11)	0.0312 (12)	0.0372 (12)	0.0013 (9)	0.0087 (10)	−0.0018 (9)
O5	0.0523 (14)	0.0594 (17)	0.0414 (14)	0.0069 (12)	0.0186 (12)	0.0011 (12)
O6	0.0476 (14)	0.0491 (15)	0.0640 (16)	−0.0027 (12)	0.0191 (12)	0.0028 (14)
O7	0.0475 (13)	0.0484 (15)	0.0392 (14)	−0.0100 (11)	0.0014 (11)	0.0018 (11)
C1	0.0296 (14)	0.0209 (13)	0.0275 (14)	−0.0008 (11)	0.0008 (11)	0.0012 (11)
C2	0.0365 (15)	0.0322 (15)	0.0234 (13)	0.0000 (12)	0.0064 (11)	0.0002 (12)
C3	0.0314 (14)	0.0313 (15)	0.0298 (15)	0.0036 (12)	0.0089 (12)	−0.0016 (12)
C4	0.0285 (13)	0.0197 (13)	0.0281 (14)	0.0028 (11)	0.0052 (11)	−0.0008 (11)
C5	0.0296 (14)	0.0258 (14)	0.0298 (14)	0.0055 (11)	0.0090 (11)	−0.0011 (11)
C6	0.0349 (15)	0.0251 (14)	0.0306 (14)	0.0007 (12)	0.0016 (12)	0.0001 (12)
N7	0.0212 (10)	0.0248 (11)	0.0238 (11)	0.0006 (9)	0.0051 (9)	0.0010 (9)
C8	0.0284 (14)	0.0328 (15)	0.0263 (14)	0.0013 (11)	0.0069 (11)	0.0026 (12)
C9	0.0389 (16)	0.0334 (16)	0.0244 (14)	−0.0006 (13)	−0.0015 (12)	0.0050 (12)
C10	0.0265 (14)	0.0296 (15)	0.0355 (15)	0.0007 (12)	−0.0049 (12)	0.0039 (12)
C11	0.0179 (12)	0.0284 (15)	0.0468 (17)	0.0033 (11)	0.0032 (12)	−0.0039 (13)
C12	0.0229 (13)	0.0282 (15)	0.0425 (17)	0.0005 (11)	0.0122 (12)	−0.0039 (12)
C13	0.0340 (15)	0.0335 (15)	0.0348 (15)	−0.0025 (13)	0.0166 (12)	−0.0080 (13)
C14	0.0397 (16)	0.0379 (17)	0.0261 (14)	−0.0018 (13)	0.0096 (12)	−0.0050 (12)
C15	0.0284 (14)	0.0307 (15)	0.0266 (14)	−0.0011 (11)	0.0023 (11)	−0.0034 (11)
N16	0.0194 (10)	0.0239 (11)	0.0257 (11)	0.0003 (9)	0.0042 (9)	−0.0011 (9)
C17	0.0188 (12)	0.0171 (12)	0.0292 (13)	−0.0001 (10)	0.0047 (10)	0.0008 (10)
C18	0.0210 (12)	0.0195 (13)	0.0334 (14)	−0.0014 (10)	0.0012 (10)	0.0017 (11)
C19	0.0186 (12)	0.0195 (13)	0.0269 (13)	−0.0016 (10)	0.0053 (10)	−0.0018 (10)
C20	0.0233 (13)	0.0210 (13)	0.0344 (15)	−0.0030 (10)	0.0106 (11)	−0.0050 (11)

Geometric parameters (Å, º)

Cu1—O3	1.9448 (17)	C4—C4^ii	1.420 (5)
Cu1—O3^i	1.9482 (17)	C5—H5	0.9300
Cu1—N7	2.012 (2)	N7—C8	1.325 (3)
Cu1—N16	2.028 (2)	N7—C17	1.358 (3)
Cu1—O4	2.259 (2)	C8—C9	1.394 (4)
Cu1—Cu1^i	2.9002 (7)	C8—H8	0.9300
O1—C6	1.261 (3)	C9—C10	1.368 (4)
O2—C6	1.251 (3)	C9—H9	0.9300
O3—Cu1^i	1.9481 (17)	C10—C18	1.400 (4)
O3—H3A	0.757 (13)	C10—H10	0.9300
O4—H4A	0.762 (13)	C11—C12	1.345 (4)
O4—H4B	0.762 (13)	C11—C18	1.432 (4)
O5—H5A	0.760 (13)	C11—H11	0.9300
O5—H5B	0.763 (13)	C12—C20	1.429 (3)
O6—H6A	0.763 (13)	C12—H12	0.9300
O6—H6B	0.766 (13)	C13—C14	1.365 (4)
O7—H7A	0.762 (13)	C13—C20	1.401 (4)
O7—H7B	0.761 (13)	C13—H13	0.9300
C1—C5	1.362 (4)	C14—C15	1.398 (4)
C1—C2	1.419 (4)	C14—H14	0.9300
C1—C6	1.508 (4)	C15—N16	1.328 (3)
C2—C3	1.359 (4)	C15—H15	0.9300
C2—H2	0.9300	N16—C19	1.355 (3)
C3—C4^ii	1.419 (4)	C17—C18	1.406 (3)
C3—H3	0.9300	C17—C19	1.428 (3)
C4—C5	1.407 (4)	C19—C20	1.404 (3)
C4—C3^ii	1.419 (4)
O3—Cu1—O3^i	83.69 (8)	C8—N7—C17	118.0 (2)
O3—Cu1—N7	167.78 (8)	C8—N7—Cu1	129.39 (17)
O3^i—Cu1—N7	96.11 (8)	C17—N7—Cu1	112.53 (16)
O3—Cu1—N16	96.16 (8)	N7—C8—C9	122.3 (2)
O3^i—Cu1—N16	169.61 (8)	N7—C8—H8	118.9
N7—Cu1—N16	81.84 (8)	C9—C8—H8	118.9
O3—Cu1—O4	92.59 (8)	C10—C9—C8	120.3 (3)
O3^i—Cu1—O4	94.76 (8)	C10—C9—H9	119.9
N7—Cu1—O4	99.61 (8)	C8—C9—H9	119.9
N16—Cu1—O4	95.62 (8)	C9—C10—C18	119.0 (2)
O3—Cu1—Cu1^i	41.89 (5)	C9—C10—H10	120.5
O3^i—Cu1—Cu1^i	41.80 (5)	C18—C10—H10	120.5
N7—Cu1—Cu1^i	136.62 (6)	C12—C11—C18	121.3 (2)
N16—Cu1—Cu1^i	137.11 (6)	C12—C11—H11	119.3
O4—Cu1—Cu1^i	94.93 (6)	C18—C11—H11	119.3
Cu1—O3—Cu1^i	96.31 (8)	C11—C12—C20	121.4 (2)
Cu1—O3—H3A	111 (2)	C11—C12—H12	119.3
Cu1^i—O3—H3A	112 (2)	C20—C12—H12	119.3
Cu1—O4—H4A	112 (3)	C14—C13—C20	119.6 (2)
Cu1—O4—H4B	112 (3)	C14—C13—H13	120.2
H4A—O4—H4B	107 (4)	C20—C13—H13	120.2
H5A—O5—H5B	108 (4)	C13—C14—C15	119.8 (3)
H6A—O6—H6B	109 (4)	C13—C14—H14	120.1
H7A—O7—H7B	102 (4)	C15—C14—H14	120.1
C5—C1—C2	118.6 (2)	N16—C15—C14	122.2 (2)
C5—C1—C6	122.0 (2)	N16—C15—H15	118.9
C2—C1—C6	119.4 (2)	C14—C15—H15	118.9
C3—C2—C1	121.1 (2)	C15—N16—C19	118.1 (2)
C3—C2—H2	119.5	C15—N16—Cu1	129.74 (17)
C1—C2—H2	119.5	C19—N16—Cu1	112.16 (16)
C2—C3—C4^ii	121.0 (2)	N7—C17—C18	123.2 (2)
C2—C3—H3	119.5	N7—C17—C19	116.7 (2)
C4^ii—C3—H3	119.5	C18—C17—C19	120.2 (2)
C5—C4—C3^ii	122.8 (2)	C10—C18—C17	117.2 (2)
C5—C4—C4^ii	119.0 (3)	C10—C18—C11	124.3 (2)
C3^ii—C4—C4^ii	118.2 (3)	C17—C18—C11	118.4 (2)
C1—C5—C4	122.1 (2)	N16—C19—C20	123.4 (2)
C1—C5—H5	118.9	N16—C19—C17	116.7 (2)
C4—C5—H5	118.9	C20—C19—C17	119.9 (2)
O2—C6—O1	123.7 (3)	C13—C20—C19	116.8 (2)
O2—C6—C1	117.6 (2)	C13—C20—C12	124.4 (2)
O1—C6—C1	118.7 (2)	C19—C20—C12	118.8 (2)
C5—C1—C2—C3	−1.1 (4)	C9—C10—C18—C17	−0.5 (4)
C6—C1—C2—C3	178.3 (3)	C9—C10—C18—C11	179.9 (3)
C1—C2—C3—C4^ii	1.1 (4)	N7—C17—C18—C10	0.3 (4)
C2—C1—C5—C4	0.2 (4)	C19—C17—C18—C10	−179.9 (2)
C6—C1—C5—C4	−179.2 (2)	N7—C17—C18—C11	−180.0 (2)
C3^ii—C4—C5—C1	−180.0 (3)	C19—C17—C18—C11	−0.2 (4)
C4^ii—C4—C5—C1	0.6 (5)	C12—C11—C18—C10	179.8 (3)
C5—C1—C6—O2	−167.8 (3)	C12—C11—C18—C17	0.1 (4)
C2—C1—C6—O2	12.9 (4)	C15—N16—C19—C20	−1.1 (4)
C5—C1—C6—O1	11.8 (4)	Cu1—N16—C19—C20	177.23 (19)
C2—C1—C6—O1	−167.6 (3)	C15—N16—C19—C17	179.4 (2)
C17—N7—C8—C9	−0.5 (4)	Cu1—N16—C19—C17	−2.3 (3)
Cu1—N7—C8—C9	176.7 (2)	N7—C17—C19—N16	−0.2 (3)
N7—C8—C9—C10	0.3 (4)	C18—C17—C19—N16	179.9 (2)
C8—C9—C10—C18	0.2 (4)	N7—C17—C19—C20	−179.8 (2)
C18—C11—C12—C20	−0.2 (4)	C18—C17—C19—C20	0.4 (4)
C20—C13—C14—C15	−1.4 (4)	C14—C13—C20—C19	0.6 (4)
C13—C14—C15—N16	1.0 (4)	C14—C13—C20—C12	−178.7 (3)
C14—C15—N16—C19	0.3 (4)	N16—C19—C20—C13	0.6 (4)
C14—C15—N16—Cu1	−177.7 (2)	C17—C19—C20—C13	−179.8 (2)
C8—N7—C17—C18	0.2 (4)	N16—C19—C20—C12	180.0 (2)
Cu1—N7—C17—C18	−177.50 (19)	C17—C19—C20—C12	−0.5 (4)
C8—N7—C17—C19	−179.7 (2)	C11—C12—C20—C13	179.7 (3)
Cu1—N7—C17—C19	2.7 (3)	C11—C12—C20—C19	0.4 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O5^iii	0.76 (1)	2.24 (2)	2.977 (3)	166 (3)
O4—H4A···O6	0.76 (1)	2.07 (2)	2.821 (3)	168 (4)
O4—H4B···O1^iii	0.76 (1)	2.01 (1)	2.769 (3)	176 (4)
O5—H5A···O1	0.76 (1)	2.27 (2)	2.993 (3)	159 (4)
O5—H5B···O2^iv	0.76 (1)	2.13 (2)	2.846 (3)	156 (4)
O6—H6A···O1	0.76 (1)	2.13 (2)	2.882 (3)	167 (4)
O6—H6B···O7	0.77 (1)	2.04 (2)	2.782 (4)	164 (4)
O7—H7A···O3^i	0.76 (1)	2.07 (1)	2.820 (3)	171 (4)
O7—H7B···O2^v	0.76 (1)	2.00 (2)	2.744 (3)	165 (4)

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