[2-Carb­oxy-4-(4-carb­oxy-3-carboxyl­atobenzoyl)benzoato]bis­(1,10-phenanthroline)cobalt(II) monohydrate

In the title compound, [Co(C₁₂H₈N₂)₂(C₁₇H₈O₉)]·H₂O, the Co atom is octa­hedrally coordinated by four N atoms from two 1,10-phenanthroline (phen) ligands and two O atoms from the 2-carb­oxy-4-(4-carb­oxy-3-carboxyl­atobenzo­yl)benzoate ligand. O...H...O hydrogen bonds link this discrete structure into a one-dimensional chain.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.055
• wR factor = 0.132
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95
PLAT432_ALERT_2_B Short Inter X...Y Contact  O1     ..  C8      ..       2.82 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C84    -   C841   ...       1.53 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1     ..  C5      ..       3.00 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   4 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1997); data reduction: SHELXTL (Siemens, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL.

[2-Carboxy-4-(4-carboxy-3-carboxylatobenzoyl)benzoato]bis(1,10- phenanthroline)cobalt(II) monohydrate

Crystal data

[Co(C12H8N2)2(C17H8O9)]·H2O	F(000) = 1628
Mr = 793.59	Dx = 1.491 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5859 reflections
a = 14.2816 (3) Å	θ = 2.8–25.7°
b = 16.8507 (4) Å	µ = 0.55 mm^−1
c = 15.0142 (4) Å	T = 293 K
β = 101.90 (1)°	Prism, red
V = 3535.6 (2) Å^3	0.25 × 0.15 × 0.05 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	6760 independent reflections
Radiation source: fine-focus sealed tube	6442 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 25.7°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.905, Tmax = 0.973	k = −18→20
18205 measured reflections	l = −18→17

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.21	w = 1/[σ^2(Fo^2) + (0.0459P)^2 + 3.3384P] where P = (Fo^2 + 2Fc^2)/3
6442 reflections	(Δ/σ)max = 0.001
516 parameters	Δρmax = 0.70 e Å^−3
6 restraints	Δρmin = −0.36 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.

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Co1	0.66553 (3)	0.61221 (2)	0.24099 (3)	0.03355 (13)
N1	0.52676 (19)	0.66869 (18)	0.19845 (19)	0.0477 (7)
N2	0.63498 (19)	0.59232 (16)	0.09858 (19)	0.0436 (6)
N3	0.74664 (19)	0.71755 (18)	0.27449 (19)	0.0470 (7)
N4	0.8083 (2)	0.56750 (19)	0.2664 (2)	0.0493 (7)
O1	0.62348 (15)	0.57504 (14)	0.35988 (16)	0.0450 (5)
O2	0.60192 (18)	0.48497 (18)	0.25345 (17)	0.0605 (7)
O8	0.38399 (15)	0.25472 (13)	0.54650 (17)	0.0489 (6)
O31	0.0930 (2)	0.11116 (16)	0.4396 (3)	0.0829 (10)
O32	−0.04985 (19)	0.16274 (18)	0.4036 (3)	0.0845 (10)
H32	−0.0745	0.2069	0.3986	0.127*
O41	−0.09203 (16)	0.40296 (15)	0.47414 (19)	0.0552 (7)
O42	−0.12477 (19)	0.2887 (2)	0.4063 (3)	0.1037 (14)
O71	0.72777 (15)	0.42326 (16)	0.43471 (18)	0.0539 (6)
H2	0.7837	0.4107	0.4542	0.081*
O72	0.70652 (18)	0.3675 (2)	0.5630 (2)	0.0756 (9)
C1	0.5925 (2)	0.5085 (2)	0.3295 (2)	0.0381 (7)
C2	0.5336 (2)	0.45942 (18)	0.3808 (2)	0.0360 (7)
C3	0.4347 (2)	0.4657 (2)	0.3529 (2)	0.0414 (7)
H3	0.4094	0.5014	0.3070	0.050*
C4	0.3732 (2)	0.4203 (2)	0.3916 (2)	0.0398 (7)
H4	0.3074	0.4258	0.3718	0.048*
C5	0.4090 (2)	0.36645 (18)	0.4599 (2)	0.0346 (7)
C6	0.5077 (2)	0.36189 (19)	0.4902 (2)	0.0377 (7)
H6	0.5326	0.3270	0.5372	0.045*
C7	0.5699 (2)	0.40762 (18)	0.4526 (2)	0.0356 (7)
C8	0.3482 (2)	0.31038 (18)	0.5001 (2)	0.0382 (7)
C11	0.4882 (2)	0.65679 (19)	0.1097 (2)	0.0414 (7)
C12	0.3958 (2)	0.6820 (2)	0.0686 (3)	0.0490 (8)
C13	0.3427 (3)	0.7203 (2)	0.1241 (3)	0.0618 (10)
H13	0.2809	0.7376	0.0999	0.074*
C14	0.3817 (3)	0.7322 (3)	0.2131 (3)	0.0689 (11)
H14	0.3469	0.7582	0.2503	0.083*
C15	0.4740 (3)	0.7053 (3)	0.2489 (3)	0.0608 (10)
H15	0.4996	0.7133	0.3104	0.073*
C16	0.3613 (3)	0.6664 (2)	−0.0265 (3)	0.0579 (10)
H16	0.3002	0.6832	−0.0543	0.070*
C21	0.5456 (2)	0.61583 (18)	0.0559 (2)	0.0399 (7)
C22	0.5088 (3)	0.6013 (2)	−0.0365 (2)	0.0469 (8)
C23	0.5680 (3)	0.5603 (2)	−0.0848 (3)	0.0557 (9)
H23	0.5465	0.5494	−0.1464	0.067*
C24	0.6567 (3)	0.5365 (2)	−0.0415 (3)	0.0571 (10)
H24	0.6960	0.5091	−0.0732	0.068*
C25	0.6881 (3)	0.5534 (2)	0.0501 (3)	0.0506 (9)
H25	0.7490	0.5369	0.0789	0.061*
C26	0.4152 (3)	0.6280 (2)	−0.0761 (3)	0.0569 (9)
H26	0.3908	0.6188	−0.1376	0.068*
C31	0.8433 (2)	0.7053 (2)	0.2919 (2)	0.0473 (8)
C32	0.9098 (3)	0.7667 (3)	0.3147 (3)	0.0562 (9)
C33	0.8741 (3)	0.8433 (3)	0.3207 (3)	0.0655 (11)
H33	0.9160	0.8858	0.3358	0.079*
C34	0.7767 (3)	0.8556 (3)	0.3041 (3)	0.0641 (10)
H34	0.7520	0.9062	0.3081	0.077*
C35	0.7162 (3)	0.7912 (2)	0.2814 (3)	0.0564 (9)
H35	0.6505	0.8001	0.2704	0.068*
C36	1.0087 (3)	0.7492 (3)	0.3321 (3)	0.0711 (12)
H36	1.0529	0.7901	0.3474	0.085*
C41	0.8761 (2)	0.6252 (2)	0.2865 (2)	0.0479 (8)
C42	0.9740 (3)	0.6097 (3)	0.3038 (3)	0.0582 (10)
C43	1.0014 (3)	0.5303 (3)	0.2984 (3)	0.0673 (12)
H43	1.0659	0.5171	0.3087	0.081*
C44	0.9343 (3)	0.4729 (3)	0.2784 (3)	0.0683 (12)
H44	0.9526	0.4202	0.2745	0.082*
C45	0.8375 (3)	0.4929 (2)	0.2635 (3)	0.0574 (9)
H45	0.7921	0.4527	0.2511	0.069*
C46	1.0398 (3)	0.6745 (3)	0.3269 (3)	0.0720 (13)
H46	1.1052	0.6645	0.3385	0.086*
C71	0.6754 (2)	0.3975 (2)	0.4896 (2)	0.0429 (8)
C81	0.2408 (2)	0.31937 (19)	0.4808 (2)	0.0373 (7)
C82	0.1860 (2)	0.25103 (19)	0.4624 (2)	0.0398 (7)
H82	0.2171	0.2029	0.4592	0.048*
C83	0.0866 (2)	0.25141 (19)	0.4485 (2)	0.0405 (7)
C84	0.0407 (2)	0.32464 (19)	0.4571 (2)	0.0381 (7)
C85	0.0969 (2)	0.39211 (19)	0.4778 (2)	0.0408 (7)
H85	0.0671	0.4401	0.4850	0.049*
C86	0.1955 (2)	0.39076 (19)	0.4883 (2)	0.0390 (7)
H86	0.2308	0.4373	0.5001	0.047*
C831	0.0412 (3)	0.1697 (2)	0.4298 (3)	0.0541 (9)
C841	−0.0664 (2)	0.3397 (2)	0.4464 (3)	0.0514 (9)
O1W	0.7723 (4)	0.4415 (3)	0.7642 (5)	0.0842 (19)	0.50
H11W	0.8163	0.4417	0.8096	0.126*	0.50
H12W	0.7812	0.4641	0.7179	0.126*	0.50
O2W	0.0960 (6)	−0.0598 (4)	0.4430 (5)	0.095 (2)	0.50
H22W	0.1292	−0.0492	0.4984	0.143*	0.50
H21W	0.0548	−0.0221	0.4266	0.143*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0235 (2)	0.0421 (2)	0.0362 (2)	0.00169 (17)	0.00874 (15)	0.00673 (18)
N1	0.0379 (15)	0.0568 (18)	0.0488 (16)	0.0032 (13)	0.0098 (12)	0.0018 (14)
N2	0.0398 (15)	0.0434 (15)	0.0499 (16)	−0.0027 (12)	0.0148 (12)	0.0051 (12)
N3	0.0392 (15)	0.0553 (18)	0.0480 (16)	0.0033 (13)	0.0121 (12)	0.0089 (14)
N4	0.0424 (15)	0.0551 (19)	0.0531 (17)	0.0050 (14)	0.0157 (13)	0.0087 (14)
O1	0.0397 (12)	0.0441 (13)	0.0533 (14)	−0.0039 (10)	0.0143 (10)	−0.0013 (11)
O2	0.0574 (15)	0.0816 (19)	0.0473 (14)	−0.0204 (14)	0.0219 (12)	−0.0117 (13)
O8	0.0346 (12)	0.0380 (13)	0.0743 (16)	0.0060 (10)	0.0118 (11)	0.0103 (12)
O31	0.0596 (18)	0.0402 (16)	0.147 (3)	−0.0056 (14)	0.0173 (19)	−0.0056 (17)
O32	0.0443 (15)	0.0576 (18)	0.153 (3)	−0.0163 (13)	0.0241 (18)	−0.022 (2)
O41	0.0292 (11)	0.0524 (15)	0.0862 (19)	0.0069 (10)	0.0172 (12)	−0.0019 (13)
O42	0.0280 (13)	0.078 (2)	0.197 (4)	−0.0132 (14)	0.0048 (18)	−0.047 (2)
O71	0.0257 (11)	0.0594 (15)	0.0798 (17)	0.0043 (11)	0.0180 (11)	0.0144 (13)
O72	0.0332 (13)	0.117 (3)	0.0736 (19)	0.0055 (15)	0.0050 (13)	0.0305 (18)
C1	0.0265 (14)	0.0492 (19)	0.0385 (17)	0.0008 (13)	0.0064 (12)	0.0003 (14)
C2	0.0322 (15)	0.0375 (16)	0.0398 (16)	−0.0035 (12)	0.0115 (12)	−0.0078 (13)
C3	0.0328 (16)	0.0489 (19)	0.0418 (17)	0.0025 (14)	0.0063 (13)	0.0023 (14)
C4	0.0252 (14)	0.0464 (18)	0.0474 (18)	−0.0007 (13)	0.0068 (13)	−0.0024 (15)
C5	0.0262 (14)	0.0364 (16)	0.0426 (17)	−0.0008 (12)	0.0104 (12)	−0.0069 (13)
C6	0.0275 (14)	0.0387 (17)	0.0476 (18)	0.0039 (12)	0.0096 (13)	−0.0006 (14)
C7	0.0256 (14)	0.0383 (17)	0.0437 (17)	0.0019 (12)	0.0093 (12)	−0.0052 (13)
C8	0.0307 (15)	0.0335 (16)	0.0525 (19)	0.0014 (13)	0.0133 (14)	−0.0063 (14)
C11	0.0350 (16)	0.0380 (17)	0.0497 (19)	−0.0036 (13)	0.0055 (14)	0.0057 (14)
C12	0.0384 (17)	0.0414 (19)	0.065 (2)	0.0022 (15)	0.0044 (16)	0.0075 (16)
C13	0.0394 (19)	0.061 (2)	0.082 (3)	0.0098 (18)	0.0066 (19)	0.002 (2)
C14	0.052 (2)	0.076 (3)	0.081 (3)	0.014 (2)	0.019 (2)	−0.009 (2)
C15	0.048 (2)	0.078 (3)	0.059 (2)	0.0126 (19)	0.0155 (18)	−0.006 (2)
C16	0.047 (2)	0.052 (2)	0.065 (2)	0.0009 (17)	−0.0104 (18)	0.0091 (19)
C21	0.0382 (16)	0.0347 (16)	0.0461 (18)	−0.0077 (13)	0.0069 (13)	0.0069 (14)
C22	0.053 (2)	0.0375 (18)	0.0500 (19)	−0.0131 (15)	0.0105 (16)	0.0051 (15)
C23	0.067 (2)	0.052 (2)	0.050 (2)	−0.0165 (19)	0.0166 (18)	−0.0031 (17)
C24	0.064 (2)	0.050 (2)	0.066 (2)	−0.0124 (18)	0.032 (2)	−0.0064 (18)
C25	0.0449 (19)	0.050 (2)	0.063 (2)	−0.0023 (16)	0.0244 (17)	0.0032 (17)
C26	0.059 (2)	0.053 (2)	0.053 (2)	−0.0087 (18)	−0.0015 (18)	0.0037 (17)
C31	0.0420 (18)	0.059 (2)	0.0442 (18)	−0.0036 (16)	0.0160 (14)	0.0079 (16)
C32	0.049 (2)	0.069 (3)	0.051 (2)	−0.0101 (19)	0.0126 (16)	0.0073 (18)
C33	0.072 (3)	0.059 (3)	0.065 (3)	−0.015 (2)	0.013 (2)	0.006 (2)
C34	0.072 (3)	0.055 (2)	0.066 (3)	−0.002 (2)	0.017 (2)	0.002 (2)
C35	0.053 (2)	0.056 (2)	0.061 (2)	0.0101 (18)	0.0142 (18)	0.0086 (18)
C36	0.045 (2)	0.087 (3)	0.082 (3)	−0.011 (2)	0.016 (2)	0.006 (2)
C41	0.0363 (17)	0.065 (2)	0.0452 (18)	0.0008 (16)	0.0141 (14)	0.0102 (16)
C42	0.0368 (18)	0.082 (3)	0.059 (2)	0.0078 (19)	0.0175 (16)	0.014 (2)
C43	0.042 (2)	0.087 (3)	0.078 (3)	0.015 (2)	0.0219 (19)	0.019 (2)
C44	0.062 (3)	0.070 (3)	0.079 (3)	0.024 (2)	0.031 (2)	0.016 (2)
C45	0.054 (2)	0.058 (2)	0.064 (2)	0.0089 (18)	0.0197 (18)	0.0103 (19)
C46	0.0341 (19)	0.107 (4)	0.076 (3)	−0.005 (2)	0.0135 (18)	0.013 (3)
C71	0.0304 (15)	0.0411 (18)	0.057 (2)	0.0004 (13)	0.0093 (15)	0.0010 (15)
C81	0.0281 (14)	0.0409 (17)	0.0451 (17)	0.0002 (13)	0.0129 (13)	0.0004 (14)
C82	0.0313 (15)	0.0355 (17)	0.0562 (19)	0.0014 (13)	0.0174 (14)	−0.0001 (14)
C83	0.0345 (16)	0.0384 (17)	0.0504 (18)	−0.0057 (13)	0.0128 (14)	−0.0009 (14)
C84	0.0251 (14)	0.0436 (18)	0.0467 (17)	−0.0020 (13)	0.0099 (12)	0.0001 (14)
C85	0.0281 (15)	0.0382 (17)	0.0574 (19)	0.0046 (13)	0.0119 (13)	−0.0019 (15)
C86	0.0277 (14)	0.0351 (16)	0.0553 (19)	−0.0009 (12)	0.0109 (13)	−0.0014 (14)
C831	0.0434 (19)	0.048 (2)	0.075 (3)	−0.0103 (17)	0.0207 (17)	−0.0061 (18)
C841	0.0280 (16)	0.051 (2)	0.076 (3)	−0.0009 (15)	0.0126 (16)	0.0042 (18)
O1W	0.069 (4)	0.056 (3)	0.137 (6)	0.005 (3)	0.042 (4)	−0.002 (4)
O2W	0.137 (6)	0.045 (3)	0.120 (6)	−0.023 (4)	0.064 (5)	−0.005 (3)

Geometric parameters (Å, º)

Co1—O1	2.093 (2)	C16—C26	1.343 (6)
Co1—N2	2.119 (3)	C16—H16	0.9300
Co1—N3	2.123 (3)	C21—C22	1.400 (5)
Co1—N4	2.133 (3)	C22—C23	1.405 (5)
Co1—N1	2.172 (3)	C22—C26	1.420 (5)
Co1—O2	2.351 (3)	C23—C24	1.359 (6)
N1—C15	1.325 (5)	C23—H23	0.9300
N1—C11	1.348 (4)	C24—C25	1.387 (5)
N2—C25	1.327 (4)	C24—H24	0.9300
N2—C21	1.363 (4)	C25—H25	0.9300
N3—C35	1.326 (5)	C26—H26	0.9300
N3—C31	1.366 (4)	C31—C32	1.398 (5)
N4—C45	1.328 (5)	C31—C41	1.437 (5)
N4—C41	1.362 (5)	C32—C33	1.398 (6)
O1—C1	1.256 (4)	C32—C36	1.413 (6)
O2—C1	1.242 (4)	C33—C34	1.377 (6)
O8—C8	1.216 (4)	C33—H33	0.9300
O31—C831	1.224 (5)	C34—C35	1.386 (6)
O32—C831	1.284 (4)	C34—H34	0.9300
O32—H32	0.8200	C35—H35	0.9300
O41—C841	1.227 (4)	C36—C46	1.343 (7)
O42—C841	1.261 (5)	C36—H36	0.9300
O71—C71	1.296 (4)	C41—C42	1.393 (5)
O71—H2	0.8200	C42—C43	1.401 (6)
O72—C71	1.211 (4)	C42—C46	1.435 (6)
C1—C2	1.502 (4)	C43—C44	1.351 (6)
C2—C3	1.392 (4)	C43—H43	0.9300
C2—C7	1.400 (4)	C44—C45	1.395 (5)
C3—C4	1.381 (4)	C44—H44	0.9300
C3—H3	0.9300	C45—H45	0.9300
C4—C5	1.386 (4)	C46—H46	0.9300
C4—H4	0.9300	C81—C86	1.381 (4)
C5—C6	1.391 (4)	C81—C82	1.387 (4)
C5—C8	1.493 (4)	C82—C83	1.392 (4)
C6—C7	1.381 (4)	C82—H82	0.9300
C6—H6	0.9300	C83—C84	1.415 (4)
C7—C71	1.505 (4)	C83—C831	1.523 (5)
C8—C81	1.510 (4)	C84—C85	1.389 (4)
C11—C12	1.403 (4)	C84—C841	1.527 (4)
C11—C21	1.439 (5)	C85—C86	1.385 (4)
C12—C13	1.395 (5)	C85—H85	0.9300
C12—C16	1.434 (5)	C86—H86	0.9300
C13—C14	1.353 (6)	O1W—H11W	0.8262
C13—H13	0.9300	O1W—H12W	0.8254
C14—C15	1.394 (5)	O2W—H22W	0.8871
C14—H14	0.9300	O2W—H21W	0.8672
C15—H15	0.9300
O1—Co1—N2	141.04 (10)	C23—C22—C26	123.7 (3)
O1—Co1—N3	106.66 (10)	C24—C23—C22	119.9 (4)
N2—Co1—N3	111.11 (10)	C24—C23—H23	120.0
O1—Co1—N4	99.99 (10)	C22—C23—H23	120.0
N2—Co1—N4	96.60 (11)	C23—C24—C25	119.5 (4)
N3—Co1—N4	78.36 (11)	C23—C24—H24	120.2
O1—Co1—N1	88.69 (10)	C25—C24—H24	120.2
N2—Co1—N1	77.71 (11)	N2—C25—C24	122.7 (4)
N3—Co1—N1	97.10 (11)	N2—C25—H25	118.6
N4—Co1—N1	171.04 (11)	C24—C25—H25	118.6
O1—Co1—O2	58.38 (9)	C16—C26—C22	121.2 (4)
N2—Co1—O2	86.19 (10)	C16—C26—H26	119.4
N3—Co1—O2	160.86 (10)	C22—C26—H26	119.4
N4—Co1—O2	91.97 (11)	N3—C31—C32	123.0 (3)
N1—Co1—O2	94.52 (11)	N3—C31—C41	117.4 (3)
C15—N1—C11	118.0 (3)	C32—C31—C41	119.6 (3)
C15—N1—Co1	128.9 (3)	C33—C32—C31	117.4 (4)
C11—N1—Co1	112.8 (2)	C33—C32—C36	123.0 (4)
C25—N2—C21	118.2 (3)	C31—C32—C36	119.6 (4)
C25—N2—Co1	127.5 (2)	C34—C33—C32	119.7 (4)
C21—N2—Co1	113.9 (2)	C34—C33—H33	120.2
C35—N3—C31	117.4 (3)	C32—C33—H33	120.2
C35—N3—Co1	129.0 (2)	C33—C34—C35	118.9 (4)
C31—N3—Co1	113.6 (2)	C33—C34—H34	120.6
C45—N4—C41	118.0 (3)	C35—C34—H34	120.6
C45—N4—Co1	128.6 (3)	N3—C35—C34	123.6 (4)
C41—N4—Co1	113.4 (2)	N3—C35—H35	118.2
C1—O1—Co1	95.67 (19)	C34—C35—H35	118.2
C1—O2—Co1	84.2 (2)	C46—C36—C32	120.9 (4)
C831—O32—H32	109.5	C46—C36—H36	119.5
C71—O71—H2	109.5	C32—C36—H36	119.5
O2—C1—O1	121.5 (3)	N4—C41—C42	123.3 (4)
O2—C1—C2	118.3 (3)	N4—C41—C31	117.2 (3)
O1—C1—C2	119.9 (3)	C42—C41—C31	119.5 (3)
C3—C2—C7	118.1 (3)	C41—C42—C43	116.7 (4)
C3—C2—C1	116.4 (3)	C41—C42—C46	119.0 (4)
C7—C2—C1	125.5 (3)	C43—C42—C46	124.3 (4)
C4—C3—C2	121.7 (3)	C44—C43—C42	120.2 (4)
C4—C3—H3	119.2	C44—C43—H43	119.9
C2—C3—H3	119.2	C42—C43—H43	119.9
C3—C4—C5	120.3 (3)	C43—C44—C45	119.7 (4)
C3—C4—H4	119.9	C43—C44—H44	120.1
C5—C4—H4	119.9	C45—C44—H44	120.1
C4—C5—C6	118.3 (3)	N4—C45—C44	122.1 (4)
C4—C5—C8	123.8 (3)	N4—C45—H45	118.9
C6—C5—C8	117.9 (3)	C44—C45—H45	118.9
C7—C6—C5	121.9 (3)	C36—C46—C42	121.3 (4)
C7—C6—H6	119.0	C36—C46—H46	119.4
C5—C6—H6	119.0	C42—C46—H46	119.4
C6—C7—C2	119.7 (3)	O72—C71—O71	124.6 (3)
C6—C7—C71	117.7 (3)	O72—C71—C7	122.3 (3)
C2—C7—C71	122.6 (3)	O71—C71—C7	113.1 (3)
O8—C8—C5	120.6 (3)	C86—C81—C82	119.1 (3)
O8—C8—C81	118.5 (3)	C86—C81—C8	123.1 (3)
C5—C8—C81	120.8 (3)	C82—C81—C8	117.6 (3)
N1—C11—C12	123.0 (3)	C81—C82—C83	122.8 (3)
N1—C11—C21	117.5 (3)	C81—C82—H82	118.6
C12—C11—C21	119.4 (3)	C83—C82—H82	118.6
C13—C12—C11	117.1 (3)	C82—C83—C84	117.9 (3)
C13—C12—C16	124.2 (3)	C82—C83—C831	114.0 (3)
C11—C12—C16	118.8 (3)	C84—C83—C831	128.1 (3)
C14—C13—C12	119.7 (4)	C85—C84—C83	118.5 (3)
C14—C13—H13	120.1	C85—C84—C841	114.0 (3)
C12—C13—H13	120.1	C83—C84—C841	127.5 (3)
C13—C14—C15	119.7 (4)	C86—C85—C84	122.6 (3)
C13—C14—H14	120.1	C86—C85—H85	118.7
C15—C14—H14	120.1	C84—C85—H85	118.7
N1—C15—C14	122.4 (4)	C81—C86—C85	119.1 (3)
N1—C15—H15	118.8	C81—C86—H86	120.4
C14—C15—H15	118.8	C85—C86—H86	120.4
C26—C16—C12	121.4 (3)	O31—C831—O32	120.7 (3)
C26—C16—H16	119.3	O31—C831—C83	118.9 (3)
C12—C16—H16	119.3	O32—C831—C83	120.4 (3)
N2—C21—C22	122.6 (3)	O41—C841—O42	122.7 (3)
N2—C21—C11	117.5 (3)	O41—C841—C84	118.1 (3)
C22—C21—C11	119.9 (3)	O42—C841—C84	119.1 (3)
C21—C22—C23	117.1 (3)	H11W—O1W—H12W	118.1
C21—C22—C26	119.3 (3)	H22W—O2W—H21W	108.6

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O32—H32···O42	0.82	1.57	2.381 (5)	170
O71—H2···O41^i	0.82	1.74	2.542 (3)	164

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