catena-Poly­[[di­aqua­calcium(II)]­bis­[μ-2-oxo-1,2-di­hydro­pyridine-1-acetato]]

Zhao, J.-G.; Gao, S.; Zhang, Z.-Y.; Huo, L.-H.; Zhao, H.

doi:10.1107/S160053680501473X

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catena-Poly[[diaquacalcium(II)]bis[μ-2-oxo-1,2-dihydropyridine-1-acetato]]

J.-G. Zhao, S. Gao, Z.-Y. Zhang, L.-H. Huo and H. Zhao

In the title coordination polymer, [Ca(2-OPA)₂(H₂O)₂]_n [2-OPA⁻ is 2-oxo-1,2-dihydropyridine-1-acetate, C₇H₆NO₃], the Ca atom is eight-coordinated by six O atoms from four 2-OPA⁻ ligands and two water molecules, and displays a dodecahedral coordination geometry. Each 2-OPA⁻ ligand bridges two adjacent Ca atoms, forming a chain along the a-axis direction. The Ca

Ca separation within the polymer is 4.1022 (8) Å. A two-dimensional supramolecular framework is further constructed by hydrogen bonds and weak π–π stacking interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501473X/rz6076sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680501473X/rz6076Isup2.hkl Contains datablock I

CCDC reference: 298701

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R factor = 0.030
wR factor = 0.073
Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.27 Ratio

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.48
           From the CIF: _reflns_number_total               3590
           Count of symmetry unique reflns         1862
           Completeness (_total/calc)            192.80%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1728
           Fraction of Friedel pairs measured     0.928
           Are heavy atom types Z>Si present          yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

catena-Poly[[diaquacalcium(II)]bis[µ-2-oxo-1,2-dihydropyridine-1-acetato]] top

Crystal data top

[Ca(C₇H₆NO₃)₂(H₂O)₂]	F(000) = 792
M_r = 380.37	D_x = 1.587 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 11561 reflections
a = 7.9996 (16) Å	θ = 3.5–27.5°
b = 8.2377 (16) Å	µ = 0.44 mm⁻¹
c = 24.153 (5) Å	T = 296 K
V = 1591.6 (6) Å³	Sheet, colorless
Z = 4	0.39 × 0.24 × 0.17 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	3590 independent reflections
Radiation source: fine-focus sealed tube	3187 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 10 pixels mm^-1	θ_max = 27.5°, θ_min = 3.4°
ω scans	h = −10→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −10→10
T_min = 0.846, T_max = 0.928	l = −31→31
13703 measured reflections

Refinement top

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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.073	w = 1/[σ²(F_o²) + (0.0479P)² + 0.2343P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
3590 reflections	Δρ_max = 0.25 e Å⁻³
239 parameters	Δρ_min = −0.18 e Å⁻³
7 restraints	Absolute structure: Flack (1983). 1739 Friedel pairs.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.11 (3)

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

	x	y	z	U_iso*/U_eq
Ca1	0.37314 (5)	0.19473 (3)	0.22263 (4)	0.02007 (8)
N1	0.6973 (3)	−0.1857 (3)	0.34417 (11)	0.0253 (6)
N2	0.5491 (3)	0.6916 (3)	0.10177 (10)	0.0226 (5)
O1	0.67497 (18)	0.08714 (17)	0.22900 (8)	0.0277 (3)
O2	0.48079 (19)	−0.0598 (2)	0.26958 (8)	0.0323 (4)
O3	0.6586 (2)	0.0689 (2)	0.37746 (8)	0.0360 (4)
O4	0.57140 (18)	0.41250 (17)	0.21624 (8)	0.0280 (4)
O5	0.76546 (18)	0.55950 (19)	0.17553 (8)	0.0319 (4)
O6	0.5904 (2)	0.43406 (19)	0.06737 (8)	0.0352 (4)
O1W	0.3737 (3)	0.2323 (3)	0.12310 (12)	0.0363 (8)
O2W	0.3748 (4)	0.2286 (4)	0.32097 (16)	0.0490 (10)
C1	0.6285 (3)	−0.0238 (2)	0.26161 (8)	0.0207 (4)
C2	0.7636 (3)	−0.1179 (3)	0.29266 (9)	0.0250 (4)
C3	0.6454 (4)	−0.0836 (4)	0.38499 (15)	0.0288 (8)
C4	0.5744 (5)	−0.1541 (5)	0.43296 (17)	0.0400 (9)
C5	0.5579 (5)	−0.3168 (5)	0.43790 (17)	0.0422 (9)
C6	0.6106 (4)	−0.4166 (5)	0.39537 (16)	0.0377 (9)
C7	0.6798 (4)	−0.3527 (4)	0.34867 (13)	0.0257 (6)
C8	0.6176 (3)	0.5232 (2)	0.18339 (8)	0.0203 (4)
C9	0.4828 (3)	0.6177 (3)	0.15259 (9)	0.0242 (4)
C10	0.6041 (4)	0.5829 (4)	0.06086 (13)	0.0247 (7)
C11	0.6697 (5)	0.6602 (5)	0.01228 (16)	0.0357 (8)
C12	0.6833 (5)	0.8236 (5)	0.00831 (18)	0.0395 (9)
C13	0.6316 (4)	0.9261 (5)	0.05234 (17)	0.0355 (10)
C14	0.5651 (4)	0.8525 (5)	0.09762 (16)	0.0339 (8)
H1W1	0.442 (3)	0.283 (4)	0.1028 (11)	0.054*
H1W2	0.296 (3)	0.190 (4)	0.1044 (11)	0.054*
H2W1	0.327 (5)	0.304 (4)	0.3397 (13)	0.074*
H2W2	0.431 (4)	0.169 (4)	0.3423 (12)	0.074*
H2A	0.8051	−0.2050	0.2694	0.030*
H2B	0.8563	−0.0461	0.3010	0.030*
H4	0.5385	−0.0873	0.4616	0.048*
H5	0.5113	−0.3613	0.4698	0.051*
H6	0.5986	−0.5285	0.3986	0.045*
H7	0.7149	−0.4203	0.3201	0.031*
H9B	0.3916	0.5452	0.1432	0.029*
H9A	0.4390	0.7021	0.1765	0.029*
H11	0.7039	0.5962	−0.0174	0.043*
H12	0.7272	0.8694	−0.0237	0.047*
H13	0.6428	1.0383	0.0503	0.043*
H14	0.5292	0.9168	0.1269	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ca1	0.01756 (14)	0.02000 (14)	0.02264 (14)	−0.00003 (17)	−0.00116 (14)	−0.0003 (3)
N1	0.0237 (11)	0.0299 (16)	0.0224 (12)	0.0027 (9)	0.0010 (8)	0.0070 (10)
N2	0.0233 (10)	0.0240 (15)	0.0204 (10)	0.0051 (9)	0.0003 (7)	0.0006 (10)
O1	0.0278 (8)	0.0246 (7)	0.0307 (9)	−0.0018 (5)	−0.0017 (7)	0.0074 (7)
O2	0.0199 (8)	0.0348 (9)	0.0421 (10)	−0.0040 (6)	−0.0046 (7)	0.0107 (7)
O3	0.0435 (11)	0.0285 (9)	0.0360 (9)	−0.0020 (7)	0.0061 (8)	−0.0036 (7)
O4	0.0256 (7)	0.0249 (7)	0.0335 (10)	−0.0022 (4)	−0.0030 (7)	0.0094 (7)
O5	0.0216 (8)	0.0340 (9)	0.0401 (9)	−0.0028 (6)	−0.0041 (7)	0.0117 (7)
O6	0.0435 (10)	0.0287 (9)	0.0334 (9)	−0.0015 (7)	0.0041 (7)	−0.0047 (7)
O1W	0.053 (2)	0.0374 (13)	0.0189 (13)	−0.0152 (9)	−0.0012 (10)	−0.0009 (9)
O2W	0.055 (3)	0.0496 (16)	0.042 (2)	0.0225 (11)	−0.0033 (12)	−0.0079 (13)
C1	0.0235 (9)	0.0175 (9)	0.0211 (8)	−0.0008 (8)	0.0002 (10)	−0.0010 (6)
C2	0.0222 (10)	0.0275 (12)	0.0253 (11)	0.0051 (8)	0.0023 (8)	0.0048 (8)
C3	0.0265 (15)	0.0323 (16)	0.0276 (15)	0.0023 (10)	−0.0003 (12)	−0.0012 (12)
C4	0.0432 (19)	0.051 (2)	0.0259 (17)	−0.0047 (15)	0.0053 (13)	−0.0030 (15)
C5	0.0419 (19)	0.059 (3)	0.0255 (17)	−0.0095 (17)	0.0021 (13)	0.0153 (16)
C6	0.0423 (19)	0.0355 (17)	0.0353 (19)	0.0000 (13)	−0.0052 (14)	0.0124 (13)
C7	0.0300 (13)	0.0191 (13)	0.0279 (14)	0.0028 (9)	−0.0020 (10)	0.0048 (11)
C8	0.0220 (9)	0.0171 (9)	0.0217 (9)	0.0034 (8)	−0.0026 (10)	−0.0022 (7)
C9	0.0217 (11)	0.0268 (12)	0.0241 (10)	0.0069 (8)	0.0031 (8)	0.0043 (8)
C10	0.0257 (14)	0.0278 (15)	0.0206 (14)	−0.0008 (10)	−0.0016 (11)	0.0050 (10)
C11	0.0401 (17)	0.0409 (18)	0.0261 (16)	0.0004 (13)	0.0089 (12)	−0.0008 (13)
C12	0.0429 (18)	0.043 (2)	0.0329 (18)	−0.0066 (15)	0.0088 (14)	0.0103 (14)
C13	0.0378 (19)	0.0270 (16)	0.0417 (19)	−0.0038 (12)	−0.0012 (14)	0.0122 (12)
C14	0.0318 (15)	0.0352 (17)	0.0347 (17)	0.0080 (12)	−0.0036 (11)	0.0004 (13)

Geometric parameters (Å, º) top

Ca1—O1	2.5766 (15)	O1W—H1W1	0.84 (3)
Ca1—O1ⁱ	2.4011 (14)	O1W—H1W2	0.84 (3)
Ca1—O2	2.5344 (16)	O2W—H2W1	0.86 (3)
Ca1—O4	2.3995 (14)	O2W—H2W2	0.84 (3)
Ca1—O4ⁱ	2.5749 (15)	C1—C2	1.527 (3)
Ca1—O5ⁱ	2.5342 (16)	C2—H2A	0.9700
Ca1—O1W	2.424 (3)	C2—H2B	0.9700
Ca1—O2W	2.392 (4)	C3—C4	1.415 (5)
O3—C3	1.274 (4)	C4—C5	1.352 (7)
O6—C10	1.241 (4)	C4—H4	0.9300
Ca1—Ca1ⁱⁱ	4.1022 (8)	C5—C6	1.382 (6)
Ca1—Ca1ⁱ	4.1022 (8)	C5—H5	0.9300
Ca1—C1	2.881 (2)	C6—C7	1.362 (5)
Ca1—C8ⁱ	2.881 (2)	C6—H6	0.9300
N1—C2	1.463 (3)	C7—H7	0.9300
N1—C3	1.361 (4)	C8—Ca1ⁱⁱ	2.881 (2)
N1—C7	1.387 (4)	C8—C9	1.524 (3)
N2—C9	1.469 (3)	C9—H9A	0.9700
N2—C10	1.404 (4)	C9—H9B	0.9700
N2—C14	1.335 (5)	C10—C11	1.435 (5)
O1—Ca1ⁱⁱ	2.4011 (14)	C11—C12	1.354 (7)
O1—C1	1.262 (3)	C11—H11	0.9300
O2—C1	1.234 (3)	C12—C13	1.419 (6)
O4—Ca1ⁱⁱ	2.5749 (15)	C12—H12	0.9300
O4—C8	1.264 (2)	C13—C14	1.359 (5)
O5—Ca1ⁱⁱ	2.5342 (16)	C13—H13	0.9300
O5—C8	1.235 (3)	C14—H14	0.9300

O1ⁱ—Ca1—O1	150.72 (4)	O4ⁱ—Ca1—C1	118.04 (5)
O1ⁱ—Ca1—O2	144.56 (6)	O4—Ca1—C8ⁱ	156.02 (6)
O1ⁱ—Ca1—O4ⁱ	69.00 (4)	O4ⁱ—Ca1—C8ⁱ	26.02 (5)
O1ⁱ—Ca1—O5ⁱ	115.01 (5)	O4—C8—Ca1ⁱⁱ	63.34 (10)
O1ⁱ—Ca1—O1W	88.23 (8)	O4—C8—C9	117.9 (2)
O2—Ca1—O1	50.97 (5)	O5ⁱ—Ca1—Ca1ⁱ	81.49 (4)
O2—Ca1—O4ⁱ	93.53 (5)	O5ⁱ—Ca1—Ca1ⁱⁱ	120.99 (4)
O2—Ca1—O5ⁱ	68.45 (4)	O5ⁱ—Ca1—C1	82.61 (5)
O4—Ca1—O1	69.00 (4)	O5ⁱ—Ca1—C8ⁱ	25.34 (6)
O4—Ca1—O1ⁱ	83.17 (4)	O5—C8—Ca1ⁱⁱ	61.43 (11)
O4ⁱ—Ca1—O1	139.82 (4)	O5—C8—O4	123.45 (19)
O4—Ca1—O2	115.00 (5)	O5—C8—C9	118.60 (18)
O4—Ca1—O4ⁱ	150.72 (4)	O6—C10—N2	120.9 (3)
O4—Ca1—O5ⁱ	144.45 (6)	O6—C10—C11	125.1 (3)
O4—Ca1—O1W	80.76 (8)	O1W—Ca1—Ca1ⁱ	88.47 (7)
O5ⁱ—Ca1—O1	93.50 (5)	O1W—Ca1—Ca1ⁱⁱ	88.28 (6)
O5ⁱ—Ca1—O4ⁱ	51.02 (5)	O1W—Ca1—C1	113.75 (8)
O1W—Ca1—O1	95.83 (8)	O1W—Ca1—C8ⁱ	75.79 (7)
O1W—Ca1—O2	123.29 (8)	O2W—Ca1—Ca1ⁱ	88.83 (7)
O1W—Ca1—O4ⁱ	89.20 (7)	O2W—Ca1—Ca1ⁱⁱ	88.19 (8)
O1W—Ca1—O5ⁱ	70.18 (7)	O2W—Ca1—C1	75.19 (8)
O2W—Ca1—O1	88.60 (8)	O2W—Ca1—C8ⁱ	113.80 (9)
O2W—Ca1—O1ⁱ	81.53 (8)	C1—Ca1—Ca1ⁱ	146.11 (4)
O2W—Ca1—O2	69.53 (9)	C1—Ca1—Ca1ⁱⁱ	56.44 (4)
O2W—Ca1—O4	88.44 (10)	C1—O1—Ca1ⁱⁱ	140.89 (14)
O2W—Ca1—O4ⁱ	96.02 (9)	C1—O1—Ca1	90.60 (13)
O2W—Ca1—O5ⁱ	122.97 (10)	C1—O2—Ca1	93.26 (12)
O2W—Ca1—O1W	165.95 (5)	C1—C2—H2A	109.5
N1—C2—C1	110.81 (18)	C1—C2—H2B	109.5
N2—C9—C8	111.38 (18)	C2—C1—Ca1	168.41 (14)
Ca1ⁱⁱ—Ca1—Ca1ⁱ	154.348 (16)	C3—N1—C7	121.7 (2)
Ca1ⁱⁱ—O1—Ca1	110.94 (5)	C3—N1—C2	119.4 (3)
Ca1—O4—Ca1ⁱⁱ	111.06 (5)	C3—C4—H4	119.4
Ca1—O1W—H1W1	130 (2)	C4—C5—C6	119.6 (3)
Ca1—O1W—H1W2	119 (2)	C4—C5—H5	120.2
Ca1—O2W—H2W1	127 (2)	C5—C4—C3	121.2 (3)
Ca1—O2W—H2W2	123 (2)	C5—C4—H4	119.4
N1—C2—H2A	109.5	C5—C6—H6	119.7
N1—C2—H2B	109.5	C6—C5—H5	120.2
N1—C3—C4	117.5 (3)	C6—C7—N1	119.3 (3)
N1—C7—H7	120.4	C6—C7—H7	120.4
N2—C9—H9A	109.4	C7—N1—C2	118.8 (2)
N2—C9—H9B	109.4	C7—C6—C5	120.6 (4)
N2—C10—C11	114.0 (3)	C7—C6—H6	119.7
N2—C14—C13	122.7 (3)	C8ⁱ—Ca1—Ca1ⁱ	56.39 (4)
N2—C14—H14	118.6	C8ⁱ—Ca1—Ca1ⁱⁱ	146.12 (4)
O1—Ca1—Ca1ⁱⁱ	33.14 (3)	C8ⁱ—Ca1—C1	102.80 (4)
O1ⁱ—Ca1—Ca1ⁱⁱ	118.53 (4)	C8—O4—Ca1	140.61 (14)
O1—Ca1—Ca1ⁱ	171.92 (3)	C8—O4—Ca1ⁱⁱ	90.64 (13)
O1ⁱ—Ca1—Ca1ⁱ	35.92 (3)	C8—O5—Ca1ⁱⁱ	93.23 (12)
O1—Ca1—C1	25.98 (6)	C8—C9—H9A	109.4
O1ⁱ—Ca1—C1	156.18 (6)	C8—C9—H9B	109.4
O1—Ca1—C8ⁱ	118.06 (5)	C9—C8—Ca1ⁱⁱ	168.83 (14)
O1ⁱ—Ca1—C8ⁱ	91.08 (5)	C10—N2—C9	115.9 (2)
O1—C1—Ca1	63.41 (11)	C10—C11—H11	119.0
O1—C1—C2	117.8 (2)	C11—C12—C13	121.0 (3)
O2—Ca1—Ca1ⁱⁱ	81.51 (4)	C11—C12—H12	119.5
O2—Ca1—Ca1ⁱ	121.00 (4)	C12—C11—C10	121.9 (3)
O2—Ca1—C1	25.31 (6)	C12—C11—H11	119.0
O2—Ca1—C8ⁱ	82.70 (5)	C12—C13—H13	121.6
O2—C1—Ca1	61.43 (11)	C13—C12—H12	119.5
O2—C1—O1	123.6 (2)	C13—C14—H14	118.6
O2—C1—C2	118.64 (18)	C14—N2—C9	120.6 (2)
O3—C3—N1	118.7 (3)	C14—N2—C10	123.4 (2)
O3—C3—C4	123.7 (3)	C14—C13—C12	116.9 (4)
O4—Ca1—Ca1ⁱ	118.59 (4)	C14—C13—H13	121.6
O4—Ca1—Ca1ⁱⁱ	35.86 (3)	H2A—C2—H2B	108.1
O4ⁱ—Ca1—Ca1ⁱ	33.08 (3)	H9B—C9—H9A	108.0
O4ⁱ—Ca1—Ca1ⁱⁱ	171.96 (3)	H1W1—O1W—H1W2	111.6 (16)
O4—Ca1—C1	91.11 (6)	H2W1—O2W—H2W2	109.6 (16)

Ca1ⁱⁱ—Ca1—O1—C1	146.61 (16)	O4ⁱ—Ca1—C1—O2	−15.66 (15)
Ca1ⁱⁱ—Ca1—O2—C1	−7.45 (12)	O4—Ca1—C1—C2	67.9 (8)
Ca1ⁱ—Ca1—O2—C1	−174.24 (11)	O4ⁱ—Ca1—C1—C2	−109.2 (8)
Ca1ⁱ—Ca1—O4—Ca1ⁱⁱ	176.90 (4)	O4—C8—C9—N2	−157.1 (2)
Ca1ⁱⁱ—Ca1—O4—C8	119.2 (3)	O5ⁱ—Ca1—O1—Ca1ⁱⁱ	148.20 (8)
Ca1ⁱ—Ca1—O4—C8	−63.9 (2)	O5ⁱ—Ca1—O1—C1	−65.19 (12)
Ca1ⁱⁱ—Ca1—C1—O1	−21.16 (10)	O5ⁱ—Ca1—O2—C1	120.77 (13)
Ca1ⁱ—Ca1—C1—O1	176.56 (9)	O5ⁱ—Ca1—O4—Ca1ⁱⁱ	−64.88 (12)
Ca1ⁱⁱ—Ca1—C1—O2	171.15 (14)	O5ⁱ—Ca1—O4—C8	54.3 (2)
Ca1ⁱ—Ca1—C1—O2	8.88 (16)	O5ⁱ—Ca1—C1—O2	−53.69 (12)
Ca1ⁱⁱ—Ca1—C1—C2	77.7 (8)	O5ⁱ—Ca1—C1—O1	113.99 (12)
Ca1ⁱ—Ca1—C1—C2	−84.6 (8)	O5ⁱ—Ca1—C1—C2	−147.2 (8)
Ca1ⁱⁱ—O1—C1—Ca1	125.4 (2)	O5—C8—C9—N2	23.7 (3)
Ca1ⁱⁱ—O1—C1—O2	138.43 (19)	O6—C10—C11—C12	−179.0 (3)
Ca1—O1—C1—O2	13.0 (2)	O1W—Ca1—O1—Ca1ⁱⁱ	77.78 (9)
Ca1ⁱⁱ—O1—C1—C2	−41.6 (3)	O1W—Ca1—O1—C1	−135.61 (13)
Ca1—O1—C1—C2	−167.03 (16)	O1W—Ca1—O2—C1	74.83 (15)
Ca1—O2—C1—O1	−13.2 (2)	O1W—Ca1—O4—C8	19.2 (2)
Ca1—O2—C1—C2	166.79 (16)	O1W—Ca1—O4—Ca1ⁱⁱ	−99.96 (9)
Ca1—O4—C8—Ca1ⁱⁱ	−125.4 (2)	O1W—Ca1—C1—O1	49.49 (14)
Ca1—O4—C8—O5	−138.78 (19)	O1W—Ca1—C1—O2	−118.19 (14)
Ca1ⁱⁱ—O4—C8—O5	−13.3 (2)	O1W—Ca1—C1—C2	148.3 (8)
Ca1—O4—C8—C9	42.1 (3)	O2W—Ca1—O1—Ca1ⁱⁱ	−88.85 (10)
Ca1ⁱⁱ—O4—C8—C9	167.51 (16)	O2W—Ca1—O1—C1	57.76 (14)
Ca1ⁱⁱ—O5—C8—O4	13.6 (2)	O2W—Ca1—O2—C1	−98.69 (15)
Ca1ⁱⁱ—O5—C8—C9	−167.28 (16)	O2W—Ca1—O4—Ca1ⁱⁱ	89.07 (9)
Ca1—C1—C2—N1	61.9 (8)	O2W—Ca1—O4—C8	−151.7 (2)
Ca1ⁱⁱ—C8—C9—N2	−63.5 (8)	O2W—Ca1—C1—O1	−118.99 (15)
N1—C3—C4—C5	−0.4 (5)	O2W—Ca1—C1—O2	73.32 (15)
N2—C10—C11—C12	2.9 (4)	O2W—Ca1—C1—C2	−20.2 (8)
O1ⁱ—Ca1—O1—Ca1ⁱⁱ	−19.0 (2)	C1—Ca1—O1—Ca1ⁱⁱ	−146.61 (16)
O1ⁱ—Ca1—O1—C1	127.59 (14)	C1—Ca1—O4—Ca1ⁱⁱ	13.92 (8)
O1—Ca1—O2—C1	6.91 (11)	C1—Ca1—O4—C8	133.1 (2)
O1ⁱ—Ca1—O2—C1	−135.98 (12)	C2—N1—C3—O3	−1.1 (4)
O1—Ca1—O4—Ca1ⁱⁱ	−0.02 (8)	C2—N1—C3—C4	176.9 (3)
O1ⁱ—Ca1—O4—Ca1ⁱⁱ	170.73 (5)	C2—N1—C7—C6	−176.8 (3)
O1—Ca1—O4—C8	119.2 (2)	C3—N1—C2—C1	−64.7 (3)
O1ⁱ—Ca1—O4—C8	−70.1 (2)	C3—N1—C7—C6	−0.8 (4)
O1ⁱ—Ca1—C1—O1	−106.38 (13)	C3—C4—C5—C6	−0.2 (4)
O1—Ca1—C1—O2	−167.7 (2)	C4—C5—C6—C7	0.4 (5)
O1ⁱ—Ca1—C1—O2	85.94 (18)	C5—C6—C7—N1	0.1 (4)
O1—Ca1—C1—C2	98.8 (8)	C7—N1—C2—C1	111.4 (2)
O1ⁱ—Ca1—C1—C2	−7.6 (8)	C7—N1—C3—O3	−177.1 (2)
O1—C1—C2—N1	154.7 (2)	C7—N1—C3—C4	0.9 (4)
O2—Ca1—O1—Ca1ⁱⁱ	−153.35 (11)	C8ⁱ—Ca1—O1—Ca1ⁱⁱ	154.77 (6)
O2—Ca1—O1—C1	−6.74 (11)	C8ⁱ—Ca1—O1—C1	−58.62 (13)
O2—Ca1—O4—C8	141.8 (2)	C8ⁱ—Ca1—O2—C1	142.49 (14)
O2—Ca1—O4—Ca1ⁱⁱ	22.57 (10)	C8ⁱ—Ca1—O4—C8	7.1 (3)
O2—Ca1—C1—O1	167.7 (2)	C8ⁱ—Ca1—O4—Ca1ⁱⁱ	−112.14 (13)
O2—Ca1—C1—C2	−93.5 (8)	C8ⁱ—Ca1—C1—O2	−38.27 (14)
O2—C1—C2—N1	−25.3 (3)	C8ⁱ—Ca1—C1—O1	129.41 (12)
O3—C3—C4—C5	177.5 (3)	C8ⁱ—Ca1—C1—C2	−131.8 (7)
O4—Ca1—O1—Ca1ⁱⁱ	0.02 (9)	C9—N2—C10—O6	2.6 (4)
O4ⁱ—Ca1—O1—Ca1ⁱⁱ	173.47 (6)	C9—N2—C10—C11	−179.2 (3)
O4—Ca1—O1—C1	146.63 (11)	C9—N2—C14—C13	177.4 (3)
O4ⁱ—Ca1—O1—C1	−39.92 (19)	C10—N2—C9—C8	64.3 (3)
O4—Ca1—O2—C1	−20.59 (15)	C10—C11—C12—C13	−0.5 (4)
O4ⁱ—Ca1—O2—C1	166.19 (13)	C10—N2—C14—C13	2.2 (4)
O4ⁱ—Ca1—O4—Ca1ⁱⁱ	−171.36 (10)	C11—C12—C13—C14	−1.4 (5)
O4ⁱ—Ca1—O4—C8	−52.2 (3)	C12—C13—C14—N2	0.6 (5)
O4—Ca1—C1—O1	−30.90 (11)	C14—N2—C9—C8	−111.3 (2)
O4ⁱ—Ca1—C1—O1	152.03 (13)	C14—N2—C10—O6	178.0 (2)
O4—Ca1—C1—O2	161.41 (13)	C14—N2—C10—C11	−3.8 (4)

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
O1W—H1W1···O6	0.84 (3)	1.92 (3)	2.753 (3)	168 (4)
O1W—H1W2···O6ⁱ	0.84 (3)	2.14 (3)	2.970 (3)	172 (3)
O2W—H2W1···O3ⁱ	0.86 (3)	1.93 (4)	2.763 (3)	163 (4)
O2W—H2W2···O3	0.84 (3)	2.16 (4)	2.958 (4)	157 (4)

Symmetry code: (i) x−1/2, −y+1/2, z.

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