μ-Aqua-bis(μ-2′-carboxybi­phenyl-2-carboxyl­ato-κ²O:O′)­bis­[bis(2′-carboxybi­phenyl-2-carboxyl­ato-κO)(1,10-phenanthroline-κ²N,N′)­cobalt(II)]

In the title complex, [Co₂(C₁₄H₉O₄)₄(C₁₂H₈N₂)₂(H₂O)], each Co²⁺ cation is surrounded by two N atoms from a 1,10-phenanthroline (phen) ligand and four O atoms [one from a water mol­ecule, one from a monodentate 2′-carboxybi­phenyl-2-carboxyl­ate (Hbpdc) ligand and two from two bridging Hbpdc ligands), thus forming a distorted CoO₄N₂ octahedron. The two Co²⁺ cations are bridged by two Hbpdc anions via their carboxyl­ate groups to produce an eight-membered dinuclear ring. The Co centres are also bridged by a water molecule, this latter species lying on a twofold axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.014 Å
• R factor = 0.117
• wR factor = 0.247
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
RFACG01_ALERT_3_C  The value of the R factor is > 0.10
            R factor given   0.117
PLAT082_ALERT_2_C High R1 Value ..................................       0.12
PLAT213_ALERT_2_C Atom C11     has ADP max/min Ratio .............       3.20 prolat
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.32 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.42 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for        C23
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         14

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

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

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.

µ-Aqua-bis(µ-2'-carboxybiphenyl-2-carboxylato-κ²O:O')bis[bis(2'- carboxybiphenyl-2-carboxylato-κO)(1,10-phenanthroline-κ²N,N')cobalt(II)]

Crystal data

[Co2(C14H9O4)4(C12H8N2)2(H2O)]	F(000) = 3008
Mr = 1461.13	Dx = 1.459 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3246 reflections
a = 32.2977 (7) Å	θ = 2.5–23.6°
b = 10.2480 (3) Å	µ = 0.58 mm^−1
c = 22.6078 (7) Å	T = 298 K
β = 117.237 (1)°	Block, red
V = 6653.2 (3) Å^3	0.41 × 0.16 × 0.14 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	5871 independent reflections
Radiation source: fine-focus sealed tube	5697 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −38→37
Tmin = 0.798, Tmax = 0.924	k = −10→12
16951 measured reflections	l = −26→26

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)] = 0.117	Hydrogen site location: difmap (O-H) and geom (C-H)
wR(F^2) = 0.247	H atoms treated by a mixture of independent and constrained refinement
S = 1.43	w = 1/[σ^2(Fo^2) + (0.0582P)^2 + 63.3018P] where P = (Fo^2 + 2Fc^2)/3
5871 reflections	(Δ/σ)max = 0.001
470 parameters	Δρmax = 0.57 e Å^−3
0 restraints	Δρmin = −1.04 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
Co1	0.93630 (3)	0.44937 (9)	0.21176 (4)	0.0211 (3)
O1	0.91006 (15)	0.3065 (5)	0.2558 (2)	0.0282 (11)
O2	0.97568 (16)	0.2064 (5)	0.3265 (3)	0.0354 (13)
O3	0.82033 (19)	0.2409 (6)	0.1823 (3)	0.0462 (15)
H3	0.8471	0.2635	0.2071	0.055*
O4	0.7501 (2)	0.3041 (8)	0.1621 (3)	0.071 (2)
O5	0.96492 (17)	0.5613 (5)	0.2962 (3)	0.0388 (13)
O6	1.04297 (16)	0.5684 (5)	0.3454 (2)	0.0330 (12)
O7	1.1151 (2)	0.6074 (6)	0.4703 (3)	0.0484 (15)
H7	1.0923	0.6027	0.4336	0.058*
O8	1.1720 (2)	0.7465 (9)	0.5245 (3)	0.077 (2)
O9	1.0000	0.3395 (7)	0.2500	0.0226 (14)
N1	0.8723 (2)	0.5496 (7)	0.1786 (3)	0.0390 (16)
N2	0.8940 (2)	0.3550 (6)	0.1187 (3)	0.0311 (14)
C1	0.8625 (3)	0.6480 (10)	0.2076 (5)	0.052 (2)
H1	0.8860	0.6794	0.2475	0.062*
C2	0.8184 (4)	0.7086 (11)	0.1813 (6)	0.070 (3)
H2	0.8130	0.7776	0.2036	0.084*
C3	0.7841 (3)	0.6640 (13)	0.1230 (6)	0.075 (4)
H3A	0.7547	0.7019	0.1049	0.090*
C4	0.7931 (3)	0.5612 (11)	0.0904 (5)	0.060 (3)
C5	0.7594 (3)	0.5054 (15)	0.0278 (6)	0.083 (4)
H5	0.7291	0.5374	0.0080	0.100*
C6	0.7706 (3)	0.4102 (14)	−0.0020 (6)	0.079 (4)
H6	0.7479	0.3788	−0.0425	0.094*
C7	0.8160 (3)	0.3541 (11)	0.0259 (4)	0.055 (3)
C8	0.8297 (4)	0.2547 (11)	−0.0037 (4)	0.062 (3)
H8	0.8082	0.2189	−0.0440	0.074*
C9	0.8745 (3)	0.2100 (10)	0.0264 (4)	0.055 (3)
H9	0.8842	0.1461	0.0063	0.066*
C10	0.9058 (3)	0.2626 (8)	0.0887 (4)	0.041 (2)
H10	0.9362	0.2308	0.1094	0.050*
C11	0.8493 (2)	0.4017 (8)	0.0884 (3)	0.037 (2)
C12	0.8381 (2)	0.5058 (8)	0.1194 (4)	0.0373 (19)
C13	0.9326 (2)	0.2238 (7)	0.3015 (3)	0.0246 (15)
C14	0.9043 (2)	0.1378 (7)	0.3240 (3)	0.0256 (15)
C15	0.9180 (3)	0.0086 (8)	0.3387 (4)	0.0405 (19)
H15	0.9455	−0.0193	0.3391	0.049*
C16	0.8910 (3)	−0.0795 (8)	0.3529 (4)	0.045 (2)
H16	0.8997	−0.1668	0.3608	0.053*
C17	0.8521 (3)	−0.0373 (9)	0.3551 (5)	0.052 (2)
H17	0.8337	−0.0959	0.3642	0.062*
C18	0.8396 (3)	0.0926 (9)	0.3441 (4)	0.042 (2)
H18	0.8134	0.1210	0.3476	0.050*
C19	0.8651 (2)	0.1818 (7)	0.3279 (3)	0.0255 (15)
C20	0.8500 (2)	0.3217 (8)	0.3210 (4)	0.0338 (18)
C21	0.8701 (3)	0.4011 (9)	0.3780 (4)	0.045 (2)
H21	0.8961	0.3716	0.4155	0.054*
C22	0.8520 (4)	0.5201 (10)	0.3790 (6)	0.069 (3)
H22	0.8662	0.5706	0.4173	0.082*
C23	0.8138 (4)	0.5678 (11)	0.3256 (7)	0.081 (4)
H23	0.8016	0.6490	0.3272	0.097*
C24	0.7939 (3)	0.4920 (10)	0.2690 (6)	0.059 (3)
H24	0.7674	0.5226	0.2325	0.070*
C25	0.8120 (2)	0.3714 (8)	0.2645 (4)	0.0381 (19)
C26	0.7912 (3)	0.3003 (9)	0.2005 (4)	0.044 (2)
C27	1.0037 (2)	0.5960 (7)	0.3413 (3)	0.0257 (15)
C28	1.0035 (2)	0.6718 (7)	0.3980 (3)	0.0272 (15)
C29	0.9755 (3)	0.6279 (8)	0.4252 (4)	0.0353 (18)
H29	0.9555	0.5579	0.4057	0.042*
C30	0.9767 (3)	0.6865 (10)	0.4811 (4)	0.050 (2)
H30	0.9585	0.6546	0.5000	0.060*
C31	1.0054 (3)	0.7936 (10)	0.5083 (4)	0.047 (2)
H31	1.0062	0.8345	0.5455	0.057*
C32	1.0326 (3)	0.8397 (8)	0.4811 (4)	0.0393 (19)
H32	1.0515	0.9118	0.5000	0.047*
C33	1.0323 (2)	0.7806 (7)	0.4257 (3)	0.0296 (16)
C34	1.0612 (3)	0.8379 (7)	0.3961 (4)	0.0334 (17)
C35	1.0413 (3)	0.9226 (7)	0.3429 (5)	0.044 (2)
H35	1.0093	0.9358	0.3234	0.052*
C36	1.0670 (4)	0.9885 (9)	0.3174 (5)	0.056 (3)
H36	1.0521	1.0439	0.2811	0.067*
C37	1.1145 (4)	0.9719 (10)	0.3459 (5)	0.061 (3)
H37	1.1321	1.0172	0.3297	0.073*
C38	1.1351 (3)	0.8883 (10)	0.3980 (5)	0.057 (3)
H38	1.1672	0.8763	0.4170	0.069*
C39	1.1098 (3)	0.8202 (9)	0.4238 (4)	0.042 (2)
C40	1.1350 (3)	0.7253 (10)	0.4775 (4)	0.046 (2)
H9A	1.008 (3)	0.288 (9)	0.224 (4)	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0157 (4)	0.0268 (5)	0.0170 (5)	−0.0002 (4)	0.0042 (3)	0.0025 (4)
O1	0.025 (2)	0.036 (3)	0.024 (2)	0.005 (2)	0.011 (2)	0.014 (2)
O2	0.023 (3)	0.050 (3)	0.037 (3)	0.008 (2)	0.017 (2)	0.014 (3)
O3	0.035 (3)	0.062 (4)	0.032 (3)	−0.008 (3)	0.007 (3)	−0.004 (3)
O4	0.022 (3)	0.100 (6)	0.068 (5)	−0.010 (3)	0.002 (3)	0.010 (4)
O5	0.027 (3)	0.046 (3)	0.038 (3)	0.001 (2)	0.011 (2)	−0.019 (3)
O6	0.028 (3)	0.038 (3)	0.031 (3)	0.001 (2)	0.012 (2)	−0.011 (2)
O7	0.038 (3)	0.060 (4)	0.033 (3)	0.010 (3)	0.003 (3)	−0.003 (3)
O8	0.033 (3)	0.120 (7)	0.049 (4)	−0.005 (4)	−0.006 (3)	−0.003 (4)
O9	0.019 (3)	0.031 (4)	0.019 (3)	0.000	0.010 (3)	0.000
N1	0.026 (3)	0.048 (4)	0.042 (4)	0.005 (3)	0.015 (3)	0.006 (3)
N2	0.026 (3)	0.037 (4)	0.021 (3)	−0.007 (3)	0.003 (3)	0.004 (3)
C1	0.029 (4)	0.068 (7)	0.052 (5)	0.011 (4)	0.013 (4)	0.011 (5)
C2	0.063 (7)	0.062 (7)	0.092 (8)	0.040 (6)	0.041 (7)	0.034 (6)
C3	0.026 (5)	0.094 (9)	0.096 (9)	0.026 (5)	0.019 (6)	0.042 (8)
C4	0.026 (4)	0.075 (7)	0.068 (7)	0.003 (5)	0.011 (4)	0.036 (6)
C5	0.029 (5)	0.113 (11)	0.074 (8)	0.004 (6)	−0.005 (5)	0.033 (8)
C6	0.034 (5)	0.104 (10)	0.055 (7)	−0.025 (6)	−0.016 (5)	0.017 (7)
C7	0.035 (5)	0.083 (7)	0.033 (5)	−0.021 (5)	0.003 (4)	0.019 (5)
C8	0.062 (7)	0.084 (8)	0.022 (4)	−0.043 (6)	0.004 (4)	−0.004 (5)
C9	0.066 (6)	0.053 (6)	0.038 (5)	−0.030 (5)	0.018 (5)	−0.014 (4)
C10	0.050 (5)	0.044 (5)	0.027 (4)	−0.017 (4)	0.014 (4)	0.000 (4)
C11	0.021 (4)	0.054 (5)	0.018 (3)	−0.014 (3)	−0.007 (3)	0.018 (4)
C12	0.024 (4)	0.046 (5)	0.032 (4)	0.002 (3)	0.003 (3)	0.013 (4)
C13	0.029 (4)	0.026 (4)	0.024 (4)	0.001 (3)	0.017 (3)	−0.009 (3)
C14	0.028 (4)	0.028 (4)	0.017 (3)	0.001 (3)	0.007 (3)	0.001 (3)
C15	0.040 (4)	0.040 (5)	0.046 (5)	0.001 (4)	0.023 (4)	0.001 (4)
C16	0.054 (5)	0.027 (4)	0.051 (5)	0.001 (4)	0.022 (4)	0.010 (4)
C17	0.050 (5)	0.047 (6)	0.061 (6)	−0.003 (4)	0.027 (5)	0.020 (5)
C18	0.029 (4)	0.058 (6)	0.045 (5)	−0.003 (4)	0.021 (4)	0.011 (4)
C19	0.020 (3)	0.035 (4)	0.015 (3)	0.001 (3)	0.002 (3)	0.002 (3)
C20	0.027 (4)	0.047 (5)	0.039 (4)	0.001 (3)	0.025 (3)	0.002 (4)
C21	0.053 (5)	0.050 (5)	0.036 (5)	0.003 (4)	0.024 (4)	−0.005 (4)
C22	0.082 (8)	0.056 (7)	0.086 (8)	0.005 (6)	0.054 (7)	−0.030 (6)
C23	0.079 (8)	0.044 (6)	0.134 (12)	0.024 (6)	0.060 (8)	−0.001 (7)
C24	0.045 (5)	0.049 (6)	0.087 (8)	0.020 (5)	0.035 (5)	0.020 (6)
C25	0.023 (4)	0.041 (5)	0.051 (5)	0.005 (3)	0.018 (4)	0.006 (4)
C26	0.032 (4)	0.045 (5)	0.045 (5)	−0.006 (4)	0.010 (4)	0.016 (4)
C27	0.030 (4)	0.023 (4)	0.024 (4)	0.005 (3)	0.013 (3)	0.001 (3)
C28	0.032 (4)	0.022 (4)	0.025 (4)	0.002 (3)	0.010 (3)	−0.005 (3)
C29	0.045 (5)	0.031 (4)	0.036 (4)	−0.001 (4)	0.024 (4)	−0.001 (3)
C30	0.048 (5)	0.069 (7)	0.041 (5)	0.008 (5)	0.027 (4)	−0.001 (5)
C31	0.045 (5)	0.070 (6)	0.024 (4)	0.011 (5)	0.013 (4)	−0.013 (4)
C32	0.036 (4)	0.042 (5)	0.033 (4)	0.001 (4)	0.009 (3)	−0.013 (4)
C33	0.025 (4)	0.036 (4)	0.020 (3)	0.010 (3)	0.004 (3)	0.002 (3)
C34	0.040 (4)	0.023 (4)	0.037 (4)	0.003 (3)	0.016 (4)	−0.002 (3)
C35	0.058 (5)	0.021 (4)	0.067 (6)	0.010 (4)	0.041 (5)	0.011 (4)
C36	0.086 (8)	0.039 (5)	0.060 (6)	0.005 (5)	0.049 (6)	0.012 (5)
C37	0.077 (7)	0.060 (7)	0.063 (6)	−0.023 (6)	0.046 (6)	−0.003 (5)
C38	0.053 (6)	0.068 (7)	0.054 (6)	−0.026 (5)	0.028 (5)	−0.022 (5)
C39	0.036 (4)	0.052 (5)	0.035 (4)	−0.007 (4)	0.012 (4)	−0.017 (4)
C40	0.033 (5)	0.062 (6)	0.032 (4)	−0.008 (4)	0.007 (4)	−0.015 (4)

Geometric parameters (Å, º)

Co1—O5	2.049 (5)	C14—C15	1.387 (11)
Co1—O6^i	2.097 (5)	C15—C16	1.391 (11)
Co1—N1	2.115 (6)	C15—H15	0.9300
Co1—N2	2.145 (6)	C16—C17	1.353 (12)
Co1—O9	2.150 (4)	C16—H16	0.9300
Co1—O1	2.150 (5)	C17—C18	1.380 (12)
O1—C13	1.276 (8)	C17—H17	0.9300
O2—C13	1.253 (8)	C18—C19	1.388 (10)
O3—C26	1.333 (10)	C18—H18	0.9300
O3—H3	0.8200	C19—C20	1.499 (11)
O4—C26	1.209 (9)	C20—C25	1.401 (11)
O5—C27	1.252 (8)	C20—C21	1.406 (11)
O6—C27	1.261 (8)	C21—C22	1.356 (13)
O6—Co1^i	2.097 (5)	C21—H21	0.9300
O7—C40	1.343 (11)	C22—C23	1.362 (16)
O7—H7	0.8200	C22—H22	0.9300
O8—C40	1.202 (9)	C23—C24	1.379 (16)
O9—Co1^i	2.150 (4)	C23—H23	0.9300
O9—H9A	0.92 (8)	C24—C25	1.391 (12)
N1—C1	1.317 (11)	C24—H24	0.9300
N1—C12	1.364 (10)	C25—C26	1.478 (12)
N2—C10	1.319 (10)	C27—C28	1.501 (9)
N2—C11	1.370 (9)	C28—C29	1.382 (10)
C1—C2	1.412 (12)	C28—C33	1.401 (10)
C1—H1	0.9300	C29—C30	1.382 (11)
C2—C3	1.356 (16)	C29—H29	0.9300
C2—H2	0.9300	C30—C31	1.387 (13)
C3—C4	1.391 (16)	C30—H30	0.9300
C3—H3A	0.9300	C31—C32	1.366 (12)
C4—C12	1.409 (11)	C31—H31	0.9300
C4—C5	1.452 (16)	C32—C33	1.388 (10)
C5—C6	1.326 (17)	C32—H32	0.9300
C5—H5	0.9300	C33—C34	1.497 (10)
C6—C7	1.427 (15)	C34—C35	1.380 (11)
C6—H6	0.9300	C34—C39	1.409 (11)
C7—C8	1.397 (15)	C35—C36	1.383 (12)
C7—C11	1.414 (11)	C35—H35	0.9300
C8—C9	1.367 (14)	C36—C37	1.376 (14)
C8—H8	0.9300	C36—H36	0.9300
C9—C10	1.411 (11)	C37—C38	1.360 (14)
C9—H9	0.9300	C37—H37	0.9300
C10—H10	0.9300	C38—C39	1.390 (12)
C11—C12	1.412 (12)	C38—H38	0.9300
C13—C14	1.515 (9)	C39—C40	1.475 (12)
C14—C19	1.384 (9)
O5—Co1—O6^i	96.5 (2)	C17—C16—H16	120.2
O5—Co1—N1	90.5 (2)	C15—C16—H16	120.2
O6^i—Co1—N1	92.0 (2)	C16—C17—C18	120.1 (8)
O5—Co1—N2	168.5 (2)	C16—C17—H17	120.0
O6^i—Co1—N2	84.1 (2)	C18—C17—H17	120.0
N1—Co1—N2	77.9 (3)	C17—C18—C19	121.6 (8)
O5—Co1—O9	88.75 (18)	C17—C18—H18	119.2
O6^i—Co1—O9	92.07 (17)	C19—C18—H18	119.2
N1—Co1—O9	175.9 (2)	C14—C19—C18	118.2 (7)
N2—Co1—O9	102.8 (2)	C14—C19—C20	124.6 (6)
O5—Co1—O1	93.2 (2)	C18—C19—C20	117.0 (6)
O6^i—Co1—O1	170.3 (2)	C25—C20—C21	118.0 (8)
N1—Co1—O1	88.1 (2)	C25—C20—C19	123.3 (7)
N2—Co1—O1	86.4 (2)	C21—C20—C19	117.8 (7)
O9—Co1—O1	87.96 (18)	C22—C21—C20	121.0 (9)
C13—O1—Co1	128.9 (4)	C22—C21—H21	119.5
C26—O3—H3	109.5	C20—C21—H21	119.5
C27—O5—Co1	140.8 (5)	C21—C22—C23	122.0 (10)
C27—O6—Co1^i	132.8 (5)	C21—C22—H22	119.0
C40—O7—H7	109.5	C23—C22—H22	119.0
Co1^i—O9—Co1	116.8 (3)	C22—C23—C24	118.0 (9)
Co1^i—O9—H9A	93 (5)	C22—C23—H23	121.0
Co1—O9—H9A	123 (6)	C24—C23—H23	121.0
C1—N1—C12	117.9 (7)	C23—C24—C25	122.3 (9)
C1—N1—Co1	127.8 (6)	C23—C24—H24	118.8
C12—N1—Co1	114.2 (5)	C25—C24—H24	118.8
C10—N2—C11	118.8 (7)	C24—C25—C20	118.6 (8)
C10—N2—Co1	128.6 (5)	C24—C25—C26	119.4 (8)
C11—N2—Co1	112.6 (5)	C20—C25—C26	122.0 (7)
N1—C1—C2	123.6 (9)	O4—C26—O3	119.4 (9)
N1—C1—H1	118.2	O4—C26—C25	123.0 (9)
C2—C1—H1	118.2	O3—C26—C25	117.2 (7)
C3—C2—C1	118.6 (11)	O5—C27—O6	126.4 (6)
C3—C2—H2	120.7	O5—C27—C28	116.7 (6)
C1—C2—H2	120.7	O6—C27—C28	116.9 (6)
C2—C3—C4	119.6 (9)	C29—C28—C33	119.7 (7)
C2—C3—H3A	120.2	C29—C28—C27	118.1 (6)
C4—C3—H3A	120.2	C33—C28—C27	122.1 (6)
C3—C4—C12	118.7 (9)	C30—C29—C28	121.0 (8)
C3—C4—C5	124.6 (10)	C30—C29—H29	119.5
C12—C4—C5	116.7 (11)	C28—C29—H29	119.5
C6—C5—C4	121.8 (10)	C29—C30—C31	118.8 (8)
C6—C5—H5	119.1	C29—C30—H30	120.6
C4—C5—H5	119.1	C31—C30—H30	120.6
C5—C6—C7	122.4 (10)	C32—C31—C30	120.8 (7)
C5—C6—H6	118.8	C32—C31—H31	119.6
C7—C6—H6	118.8	C30—C31—H31	119.6
C8—C7—C11	117.9 (9)	C31—C32—C33	121.0 (8)
C8—C7—C6	124.7 (10)	C31—C32—H32	119.5
C11—C7—C6	117.4 (11)	C33—C32—H32	119.5
C9—C8—C7	120.0 (8)	C32—C33—C28	118.6 (7)
C9—C8—H8	120.0	C32—C33—C34	119.0 (7)
C7—C8—H8	120.0	C28—C33—C34	122.3 (6)
C8—C9—C10	118.8 (10)	C35—C34—C39	116.6 (8)
C8—C9—H9	120.6	C35—C34—C33	119.9 (7)
C10—C9—H9	120.6	C39—C34—C33	123.1 (7)
N2—C10—C9	122.8 (9)	C34—C35—C36	122.8 (9)
N2—C10—H10	118.6	C34—C35—H35	118.6
C9—C10—H10	118.6	C36—C35—H35	118.6
N2—C11—C12	117.9 (6)	C37—C36—C35	119.8 (9)
N2—C11—C7	121.5 (9)	C37—C36—H36	120.1
C12—C11—C7	120.4 (8)	C35—C36—H36	120.1
N1—C12—C4	121.6 (9)	C38—C37—C36	118.9 (9)
N1—C12—C11	117.3 (7)	C38—C37—H37	120.6
C4—C12—C11	121.1 (8)	C36—C37—H37	120.6
O2—C13—O1	124.3 (6)	C37—C38—C39	122.1 (9)
O2—C13—C14	118.8 (6)	C37—C38—H38	119.0
O1—C13—C14	116.8 (6)	C39—C38—H38	119.0
C19—C14—C15	119.8 (7)	C38—C39—C34	119.8 (9)
C19—C14—C13	122.7 (6)	C38—C39—C40	117.8 (8)
C15—C14—C13	117.4 (6)	C34—C39—C40	122.3 (8)
C14—C15—C16	120.6 (7)	O8—C40—O7	119.9 (9)
C14—C15—H15	119.7	O8—C40—C39	124.0 (9)
C16—C15—H15	119.7	O7—C40—C39	116.1 (7)
C17—C16—C15	119.5 (8)

Symmetry code: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.82	1.87	2.684 (7)	173
O7—H7···O6	0.82	1.93	2.745 (7)	172
O9—H9A···O2^i	0.92 (8)	1.68 (8)	2.590 (6)	174 (8)
O9—H9A···O1^i	0.92 (8)	2.47 (8)	2.986 (5)	116 (7)

Symmetry code: (i) −x+2, y, −z+1/2.