catena-Poly­[[[di-μ-chloro-bis­[(5-nitro-­1,10-phenanthroline)copper(II)]]-μ-terephthalato] bis(N,N′-di­methyl­form­amide)]

Xiao, H.-P.; Zhu, L.-G.

doi:10.1107/S1600536803021445

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catena-Poly[[[di-μ-chloro-bis[(5-nitro-1,10-phenanthroline)copper(II)]]-μ-terephthalato] bis(N,N′-dimethylformamide)]

H.-P. Xiao and L.-G. Zhu

In the structure of the title complex, {[Cu₂Cl₂(C₈H₄O₄)(C₁₂H₇N₃O₂)₂]·2C₃H₇NO}_n, each copper cation is surrounded by one O atom from a terephthalate (ta) ligand, two bridging Cl atoms, and two N atoms from a 5-nitro-1,10-phenanthroline ligand. Dimeric blocks of [Cu₂(C₁₂H₇N₃O₂)₂(ta)] are held together by two μ-chloro bridges, which create a one-dimensional architecture. There is a center of symmetry halfway between the two Cu atoms and the two Cl atoms and at the center of the phenyl ring of the ta group.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021445/lh6116sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021445/lh6116Isup2.hkl Contains datablock I

CCDC reference: 226637

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.049
wR factor = 0.124
Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.99

Alert level C
CHEMW01_ALERT_1_C  The ratio of given/expected molecular weight as calculated
            from the _chemical_formula_sum lies outside
            the range 0.99 <> 1.01
            Calculated formula weight =   934.6944
            Formula weight given      =   958.7000
CHEMW01_ALERT_1_C  The difference between the given and expected weight for
            compound is greater 1 mass unit. Check that all hydrogen
            atoms have been taken into account.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       2.00 Ratio
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...          9
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.96 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         O2
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         N3
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors ....        C17
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....         N4

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C36 H32 Cl2 Cu2 N8 O10
            Atom count from _chemical_formula_moiety:C38 H32 Cl2 Cu2 N8 O10
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C36 H32 Cl2 Cu2 N8 O10
            Atom count from the _atom_site data:  C38 H32 Cl2 Cu2 N8 O10
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    1
           From the CIF: _chemical_formula_sum  C36 H32 Cl2 Cu2 N8 O10
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         36.00     38.00   -2.00
           H         32.00     32.00    0.00
           Cl         2.00      2.00    0.00
           Cu         2.00      2.00    0.00
           N          8.00      8.00    0.00
           O         10.00     10.00    0.00

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

catena-Poly[[[di-µ-chloro-bis[(5-nitro-1,10-phenanthroline)copper(II)]]- µ-terephthalato] bis(N,N'-dimethylformamide)] top

Crystal data top

[Cu₂Cl₂(C₈H₄O₄)(C₁₂H₇N₃O₂)₂]·2C₃H₇NO	Z = 1
M_r = 958.7	F(000) = 488
Triclinic, P1	D_x = 1.603 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4185 (11) Å	Cell parameters from 2222 reflections
b = 10.2030 (12) Å	θ = 4.8–53.3°
c = 12.3617 (15) Å	µ = 1.27 mm⁻¹
α = 106.223 (2)°	T = 293 K
β = 93.856 (2)°	Needle, green
γ = 116.698 (2)°	0.53 × 0.39 × 0.19 mm
V = 993.0 (2) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4022 independent reflections
Radiation source: fine-focus sealed tube	3093 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
φ and ω scans	θ_max = 26.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.504, T_max = 0.786	k = −11→12
5614 measured reflections	l = −15→15

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) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ²(F_o²) + (0.0588P)²] where P = (F_o² + 2F_c²)/3
4022 reflections	(Δ/σ)_max < 0.001
308 parameters	Δρ_max = 0.72 e Å⁻³
5 restraints	Δρ_min = −0.39 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Cu	0.35716 (5)	0.02614 (5)	0.42589 (4)	0.03572 (16)
Cl	0.36022 (11)	−0.20081 (10)	0.40832 (8)	0.0441 (2)
O1	0.4602 (3)	0.0541 (3)	0.2983 (2)	0.0460 (6)
O2	0.2117 (3)	−0.0962 (4)	0.1874 (3)	0.0657 (8)
O3	0.0841 (6)	0.5735 (5)	0.6293 (4)	0.1127 (15)
O4	0.0465 (5)	0.5253 (4)	0.7813 (4)	0.0969 (13)
O5	0.4639 (8)	0.5256 (11)	0.8090 (6)	0.211 (4)
N1	0.3133 (3)	0.2082 (3)	0.4399 (3)	0.0395 (7)
N2	0.2317 (3)	0.0137 (3)	0.5534 (2)	0.0349 (6)
N3	0.0814 (4)	0.5005 (4)	0.6900 (4)	0.0616 (10)
N4	0.6739 (9)	0.5367 (9)	0.9093 (5)	0.1156 (18)
C1	0.3545 (5)	0.3004 (5)	0.3779 (4)	0.0521 (10)
C2	0.3218 (5)	0.4247 (5)	0.3989 (4)	0.0572 (11)
C3	0.2487 (5)	0.4553 (5)	0.4856 (4)	0.0547 (10)
C4	0.2020 (4)	0.3605 (4)	0.5533 (3)	0.0426 (8)
C5	0.1207 (4)	0.3707 (4)	0.6464 (3)	0.0444 (9)
C6	0.0732 (4)	0.2683 (4)	0.7043 (3)	0.0453 (9)
C7	0.1086 (4)	0.1428 (4)	0.6755 (3)	0.0391 (8)
C8	0.0666 (5)	0.0332 (5)	0.7311 (4)	0.0472 (9)
C9	0.1090 (5)	−0.0809 (5)	0.6984 (4)	0.0483 (9)
C10	0.1926 (4)	−0.0869 (4)	0.6102 (3)	0.0442 (9)
C11	0.1926 (4)	0.1281 (4)	0.5869 (3)	0.0355 (7)
C12	0.2376 (4)	0.2356 (4)	0.5247 (3)	0.0373 (8)
C13	0.3604 (5)	−0.0196 (5)	0.2010 (4)	0.0464 (9)
C14	0.4328 (4)	−0.0087 (4)	0.0970 (3)	0.0420 (8)
C15	0.5967 (5)	0.0940 (5)	0.1082 (4)	0.0543 (10)
C16	0.3388 (5)	−0.1021 (5)	−0.0128 (4)	0.0547 (10)
C17	0.5454 (15)	0.470 (3)	0.8513 (10)	0.403 (18)
H17	0.4928	0.3615	0.8318	0.484*
C18	0.7610 (18)	0.7020 (14)	0.9382 (10)	0.278 (8)
H18A	0.8661	0.7437	0.9870	0.417*
H18B	0.7010	0.7472	0.9783	0.417*
H18C	0.7747	0.7265	0.8688	0.417*
C19	0.7571 (17)	0.4681 (17)	0.9510 (10)	0.253 (7)
H19A	0.6792	0.3714	0.9577	0.379*
H19B	0.8274	0.5382	1.0254	0.379*
H19C	0.8211	0.4482	0.8980	0.379*
H1	0.409 (4)	0.275 (3)	0.316 (3)	0.025 (8)*
H2	0.365 (6)	0.478 (6)	0.351 (4)	0.099 (18)*
H3	0.238 (5)	0.542 (4)	0.520 (4)	0.078 (15)*
H4	0.026 (5)	0.299 (5)	0.776 (4)	0.061 (12)*
H5	0.006 (4)	0.041 (5)	0.784 (3)	0.064 (13)*
H6	0.067 (5)	−0.168 (4)	0.719 (4)	0.076 (14)*
H7	0.220 (4)	−0.175 (4)	0.580 (3)	0.051 (10)*
H8	0.669 (5)	0.176 (5)	0.185 (4)	0.076 (14)*
H9	0.230 (3)	−0.165 (5)	−0.025 (4)	0.098 (17)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.0431 (3)	0.0419 (3)	0.0379 (3)	0.0264 (2)	0.02044 (19)	0.0237 (2)
Cl	0.0537 (5)	0.0390 (5)	0.0498 (5)	0.0278 (4)	0.0185 (4)	0.0193 (4)
O1	0.0541 (15)	0.0625 (17)	0.0374 (14)	0.0320 (14)	0.0257 (13)	0.0302 (13)
O2	0.0502 (17)	0.097 (2)	0.0620 (19)	0.0338 (17)	0.0346 (15)	0.0438 (17)
O3	0.184 (4)	0.107 (3)	0.129 (4)	0.116 (3)	0.079 (3)	0.068 (3)
O4	0.130 (3)	0.079 (2)	0.107 (3)	0.072 (2)	0.065 (3)	0.024 (2)
O5	0.106 (5)	0.361 (11)	0.132 (6)	0.067 (6)	0.028 (4)	0.116 (6)
N1	0.0417 (16)	0.0391 (16)	0.0450 (17)	0.0194 (14)	0.0116 (14)	0.0248 (14)
N2	0.0348 (15)	0.0403 (16)	0.0384 (16)	0.0220 (13)	0.0146 (13)	0.0180 (13)
N3	0.062 (2)	0.043 (2)	0.079 (3)	0.0291 (18)	0.016 (2)	0.015 (2)
N4	0.127 (5)	0.157 (6)	0.073 (4)	0.075 (5)	0.028 (3)	0.043 (4)
C1	0.056 (2)	0.053 (2)	0.058 (3)	0.028 (2)	0.019 (2)	0.030 (2)
C2	0.067 (3)	0.054 (3)	0.069 (3)	0.031 (2)	0.025 (2)	0.042 (2)
C3	0.057 (3)	0.043 (2)	0.073 (3)	0.027 (2)	0.019 (2)	0.027 (2)
C4	0.0384 (19)	0.0330 (19)	0.054 (2)	0.0155 (16)	0.0059 (17)	0.0160 (17)
C5	0.039 (2)	0.0331 (19)	0.057 (2)	0.0202 (17)	0.0109 (18)	0.0057 (17)
C6	0.041 (2)	0.039 (2)	0.050 (2)	0.0170 (17)	0.0141 (18)	0.0092 (18)
C7	0.0325 (18)	0.041 (2)	0.042 (2)	0.0179 (16)	0.0092 (15)	0.0123 (16)
C8	0.043 (2)	0.057 (2)	0.048 (2)	0.0245 (19)	0.0209 (18)	0.0243 (19)
C9	0.051 (2)	0.054 (2)	0.053 (2)	0.026 (2)	0.0245 (19)	0.035 (2)
C10	0.046 (2)	0.052 (2)	0.053 (2)	0.0287 (19)	0.0246 (18)	0.0302 (19)
C11	0.0311 (17)	0.0360 (18)	0.0403 (19)	0.0160 (15)	0.0086 (15)	0.0149 (16)
C12	0.0340 (18)	0.0354 (18)	0.041 (2)	0.0169 (15)	0.0072 (15)	0.0120 (16)
C13	0.047 (2)	0.057 (2)	0.051 (2)	0.030 (2)	0.0255 (19)	0.031 (2)
C14	0.041 (2)	0.055 (2)	0.039 (2)	0.0240 (18)	0.0187 (16)	0.0268 (18)
C15	0.045 (2)	0.063 (3)	0.047 (2)	0.015 (2)	0.015 (2)	0.026 (2)
C16	0.036 (2)	0.070 (3)	0.051 (3)	0.014 (2)	0.0177 (19)	0.029 (2)
C17	0.121 (10)	0.88 (5)	0.088 (8)	0.168 (17)	0.030 (7)	0.122 (16)
C18	0.36 (2)	0.155 (11)	0.173 (13)	0.037 (12)	0.018 (12)	0.008 (9)
C19	0.386 (19)	0.404 (19)	0.206 (12)	0.314 (17)	0.160 (13)	0.208 (14)

Geometric parameters (Å, º) top

Cu—O1	1.928 (2)	C4—C5	1.430 (5)
Cu—N2	2.031 (3)	C5—C6	1.358 (5)
Cu—N1	2.042 (3)	C6—C7	1.423 (5)
Cu—Cl	2.2781 (9)	C6—H4	1.05 (4)
Cu—Clⁱ	2.7248 (11)	C7—C8	1.395 (5)
Cl—Cuⁱ	2.7248 (11)	C7—C11	1.407 (5)
O1—C13	1.267 (5)	C8—C9	1.362 (5)
O2—C13	1.230 (4)	C8—H5	0.91 (4)
O3—N3	1.190 (5)	C9—C10	1.391 (5)
O4—N3	1.188 (5)	C9—H6	0.91 (4)
O5—C17	1.30 (2)	C10—H7	1.02 (4)
N1—C1	1.318 (5)	C11—C12	1.440 (5)
N1—C12	1.343 (4)	C13—C14	1.502 (5)
N2—C10	1.334 (4)	C14—C16	1.375 (5)
N2—C11	1.343 (4)	C14—C15	1.392 (5)
N3—C5	1.500 (5)	C15—C16ⁱⁱ	1.368 (6)
N4—C17	1.145 (12)	C15—H8	1.01 (4)
N4—C19	1.418 (10)	C16—C15ⁱⁱ	1.368 (6)
N4—C18	1.423 (12)	C16—H9	0.91 (4)
C1—C2	1.395 (6)	C17—H17	0.9300
C1—H1	0.99 (3)	C18—H18A	0.9600
C2—C3	1.352 (6)	C18—H18B	0.9600
C2—H2	0.91 (5)	C18—H18C	0.9600
C3—C4	1.396 (5)	C19—H19A	0.9600
C3—H3	0.92 (5)	C19—H19B	0.9600
C4—C12	1.418 (5)	C19—H19C	0.9600

O1—Cu—N2	171.33 (10)	C11—C7—C6	118.7 (3)
O1—Cu—N1	92.19 (11)	C9—C8—C7	119.2 (3)
N2—Cu—N1	79.82 (11)	C9—C8—H5	125 (3)
O1—Cu—Cl	93.53 (8)	C7—C8—H5	115 (3)
N2—Cu—Cl	93.95 (8)	C8—C9—C10	119.7 (3)
N1—Cu—Cl	170.34 (8)	C8—C9—H6	124 (3)
O1—Cu—Clⁱ	95.33 (8)	C10—C9—H6	115 (3)
N2—Cu—Clⁱ	88.71 (8)	N2—C10—C9	122.7 (3)
N1—Cu—Clⁱ	94.63 (8)	N2—C10—H7	116 (2)
Cl—Cu—Clⁱ	92.59 (3)	C9—C10—H7	122 (2)
Cu—Cl—Cuⁱ	87.41 (3)	N2—C11—C7	123.2 (3)
C13—O1—Cu	113.3 (2)	N2—C11—C12	116.4 (3)
C1—N1—C12	118.5 (3)	C7—C11—C12	120.5 (3)
C1—N1—Cu	127.3 (3)	N1—C12—C4	123.8 (3)
C12—N1—Cu	114.2 (2)	N1—C12—C11	115.4 (3)
C10—N2—C11	117.7 (3)	C4—C12—C11	120.8 (3)
C10—N2—Cu	128.2 (2)	O2—C13—O1	124.4 (4)
C11—N2—Cu	114.0 (2)	O2—C13—C14	119.3 (4)
O4—N3—O3	122.6 (4)	O1—C13—C14	116.3 (3)
O4—N3—C5	119.8 (4)	C16—C14—C15	117.7 (4)
O3—N3—C5	117.6 (4)	C16—C14—C13	120.8 (3)
C17—N4—C19	125.4 (16)	C15—C14—C13	121.5 (4)
C17—N4—C18	117.8 (15)	C16ⁱⁱ—C15—C14	120.9 (4)
C19—N4—C18	116.8 (10)	C16ⁱⁱ—C15—H8	117 (3)
N1—C1—C2	121.6 (4)	C14—C15—H8	122 (3)
N1—C1—H1	115.7 (18)	C15ⁱⁱ—C16—C14	121.4 (4)
C2—C1—H1	122.6 (18)	C15ⁱⁱ—C16—H9	117 (3)
C3—C2—C1	120.4 (4)	C14—C16—H9	121 (3)
C3—C2—H2	131 (3)	N4—C17—O5	128 (2)
C1—C2—H2	109 (3)	N4—C17—H17	115.9
C2—C3—C4	120.1 (4)	O5—C17—H17	115.9
C2—C3—H3	131 (3)	N4—C18—H18A	109.5
C4—C3—H3	108 (3)	N4—C18—H18B	109.5
C3—C4—C12	115.6 (4)	H18A—C18—H18B	109.5
C3—C4—C5	128.8 (3)	N4—C18—H18C	109.5
C12—C4—C5	115.6 (3)	H18A—C18—H18C	109.5
C6—C5—C4	124.7 (3)	H18B—C18—H18C	109.5
C6—C5—N3	113.5 (3)	N4—C19—H19A	109.5
C4—C5—N3	121.8 (3)	N4—C19—H19B	109.5
C5—C6—C7	119.8 (3)	H19A—C19—H19B	109.5
C5—C6—H4	115 (2)	N4—C19—H19C	109.5
C7—C6—H4	125 (2)	H19A—C19—H19C	109.5
C8—C7—C11	117.5 (3)	H19B—C19—H19C	109.5
C8—C7—C6	123.9 (3)

O1—Cu—Cl—Cuⁱ	95.51 (8)	C6—C7—C8—C9	−178.7 (4)
N2—Cu—Cl—Cuⁱ	−88.88 (8)	C7—C8—C9—C10	−0.2 (6)
Clⁱ—Cu—Cl—Cuⁱ	0.0	C11—N2—C10—C9	2.4 (6)
N1—Cu—O1—C13	−87.5 (3)	Cu—N2—C10—C9	178.4 (3)
Cl—Cu—O1—C13	84.7 (2)	C8—C9—C10—N2	−1.2 (6)
Clⁱ—Cu—O1—C13	177.7 (2)	C10—N2—C11—C7	−2.2 (5)
O1—Cu—N1—C1	−1.6 (3)	Cu—N2—C11—C7	−178.7 (3)
N2—Cu—N1—C1	−178.2 (3)	C10—N2—C11—C12	179.5 (3)
Clⁱ—Cu—N1—C1	93.9 (3)	Cu—N2—C11—C12	2.9 (4)
O1—Cu—N1—C12	−179.8 (2)	C8—C7—C11—N2	0.8 (5)
N2—Cu—N1—C12	3.6 (2)	C6—C7—C11—N2	−180.0 (3)
Clⁱ—Cu—N1—C12	−84.2 (2)	C8—C7—C11—C12	179.1 (3)
N1—Cu—N2—C10	−179.6 (3)	C6—C7—C11—C12	−1.7 (5)
Cl—Cu—N2—C10	7.8 (3)	C1—N1—C12—C4	−1.4 (5)
Clⁱ—Cu—N2—C10	−84.7 (3)	Cu—N1—C12—C4	177.0 (3)
N1—Cu—N2—C11	−3.5 (2)	C1—N1—C12—C11	178.5 (3)
Cl—Cu—N2—C11	−176.1 (2)	Cu—N1—C12—C11	−3.1 (4)
Clⁱ—Cu—N2—C11	91.4 (2)	C3—C4—C12—N1	1.0 (5)
C12—N1—C1—C2	0.3 (6)	C5—C4—C12—N1	−180.0 (3)
Cu—N1—C1—C2	−177.8 (3)	C3—C4—C12—C11	−178.9 (3)
N1—C1—C2—C3	1.1 (7)	C5—C4—C12—C11	0.2 (5)
C1—C2—C3—C4	−1.4 (7)	N2—C11—C12—N1	0.1 (5)
C2—C3—C4—C12	0.4 (6)	C7—C11—C12—N1	−178.2 (3)
C2—C3—C4—C5	−178.4 (4)	N2—C11—C12—C4	−180.0 (3)
C3—C4—C5—C6	176.9 (4)	C7—C11—C12—C4	1.6 (5)
C12—C4—C5—C6	−2.0 (6)	Cu—O1—C13—O2	3.1 (5)
C3—C4—C5—N3	−3.8 (6)	Cu—O1—C13—C14	−177.5 (2)
C12—C4—C5—N3	177.3 (3)	O2—C13—C14—C16	−10.2 (6)
O4—N3—C5—C6	15.5 (6)	O1—C13—C14—C16	170.4 (4)
O3—N3—C5—C6	−163.3 (4)	O2—C13—C14—C15	170.6 (4)
O4—N3—C5—C4	−163.9 (4)	O1—C13—C14—C15	−8.8 (5)
O3—N3—C5—C4	17.3 (6)	C16—C14—C15—C16ⁱⁱ	0.4 (7)
C4—C5—C6—C7	2.0 (6)	C13—C14—C15—C16ⁱⁱ	179.6 (4)
N3—C5—C6—C7	−177.4 (3)	C15—C14—C16—C15ⁱⁱ	−0.4 (7)
C5—C6—C7—C8	179.1 (4)	C13—C14—C16—C15ⁱⁱ	−179.6 (4)
C5—C6—C7—C11	0.0 (5)	C19—N4—C17—O5	−178.9 (10)
C11—C7—C8—C9	0.5 (6)	C18—N4—C17—O5	−2.0 (17)

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

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