(2,9-Dimethyl-1,10-phenanthroline-κ(2)N,N')bis-(2-meth-oxy-benzoato-κ(2)O(1),O(1'))cadmium.

In the title compound, [Cd(C(8)H(7)O(3))(2)(C(14)H(12)N(2))], the Cd(II) ion is coordinated by two N atoms from a 2,9-dimethyl-1,10-phenanthroline (dmphen) ligand and four O atoms from two 2-meth-oxy-benzoate anions in a distorted octa-hedral environment. Two O atoms of one bidentate 2-meth-oxy-benzoate ligand are each disordered over two positions, with site-occupancy factors of 0.579 (4) and 0.421 (4). In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming a two-dimensional network lieing parallel to the bc plane. The crystal packing is further stablized by π-π stacking inter-actions between the dmphen rings of neighboring mol-ecules, with distances between their parallel dmphen ring planes of 3.517 (3) and 3.610 (3) Å.

Related literature

For features of transition metal complexes with n class="Chemical">1,10-phenanthroline and their derivatives, see: Dhar et al. (2003 ▶); Mizuno et al. (2002 ▶); Wall et al. (1999 ▶). For related structures, see: Harvey et al. (2000 ▶); Ding et al. (2005 ▶); Cui & Zhang (2011 ▶)

Experimental

Crystal data

[Cd(C8H7O3)2(C14n class="Species">H12N2)]

M = 622.93

Monoclinic,

a = 16.9045 (12) Å

b = 8.0547 (6) Å

c = 19.3625 (14) Å

β = 101.877 (1)°

V = 2580.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.90 mm−1

T = 296 K

0.48 × 0.26 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.673, T max = 0.863

18898 measured reflections

4803 independent reflections

4307 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.060

S = 1.02

4803 reflections

363 parameters

44 restraints

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.47 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010835/bg2438sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010835/bg2438Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cd(C8H7O3)2(C14H12N2)]	F(000) = 1264
Mr = 622.93	Dx = 1.604 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9957 reflections
a = 16.9045 (12) Å	θ = 2.5–28.2°
b = 8.0547 (6) Å	µ = 0.90 mm−1
c = 19.3625 (14) Å	T = 296 K
β = 101.877 (1)°	Block, colourless
V = 2580.0 (3) Å3	0.48 × 0.26 × 0.17 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	4803 independent reflections
Radiation source: fine-focus sealed tube	4307 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
phi and ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −20→20
Tmin = 0.673, Tmax = 0.863	k = −9→9
18898 measured reflections	l = −23→23

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0297P)2 + 1.5264P] where P = (Fo2 + 2Fc2)/3
4803 reflections	(Δ/σ)max = 0.001
363 parameters	Δρmax = 0.59 e Å−3
44 restraints	Δρmin = −0.47 e Å−3

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.30422 (17)	0.4057 (4)	0.12323 (16)	0.0450 (4)	0.579 (4)
O2	0.20884 (17)	0.2183 (4)	0.12535 (17)	0.0494 (4)	0.579 (4)
O1'	0.2860 (3)	0.4050 (6)	0.1036 (2)	0.0450 (4)	0.421 (4)
O2'	0.2352 (3)	0.1914 (5)	0.1509 (2)	0.0494 (4)	0.421 (4)
Cd1	0.307440 (8)	0.144637 (19)	0.062350 (7)	0.03648 (5)
O3	0.15835 (11)	0.2486 (2)	0.25184 (8)	0.0552 (4)
O4	0.20186 (9)	0.05972 (19)	−0.02720 (8)	0.0483 (4)
O5	0.25548 (9)	−0.12268 (18)	0.05286 (8)	0.0460 (4)
O6	0.04132 (8)	−0.00151 (19)	−0.07279 (8)	0.0473 (4)
N1	0.43234 (10)	0.0689 (2)	0.13255 (9)	0.0425 (4)
N2	0.40861 (10)	0.2261 (2)	0.00289 (9)	0.0404 (4)
C1	0.44175 (16)	−0.0095 (3)	0.19443 (12)	0.0563 (6)
C2	0.51880 (18)	−0.0427 (4)	0.23466 (15)	0.0736 (9)
H2	0.5244	−0.0980	0.2775	0.088*
C3	0.58528 (18)	0.0059 (4)	0.21110 (17)	0.0778 (9)
H3	0.6364	−0.0158	0.2381	0.093*
C4	0.57759 (14)	0.0884 (3)	0.14638 (16)	0.0625 (7)
C5	0.64459 (16)	0.1445 (4)	0.1188 (2)	0.0816 (10)
H5	0.6968	0.1268	0.1445	0.098*
C6	0.63385 (15)	0.2224 (4)	0.0567 (2)	0.0784 (9)
H6	0.6789	0.2588	0.0404	0.094*
C7	0.55435 (14)	0.2517 (3)	0.01409 (15)	0.0587 (6)
C8	0.54051 (17)	0.3281 (3)	−0.05163 (17)	0.0725 (8)
H8	0.5840	0.3638	−0.0704	0.087*
C9	0.4639 (2)	0.3511 (3)	−0.08871 (15)	0.0700 (8)
H9	0.4551	0.4006	−0.1330	0.084*
C10	0.39695 (15)	0.2994 (3)	−0.05982 (12)	0.0520 (6)
C11	0.48584 (12)	0.2002 (3)	0.03993 (12)	0.0443 (5)
C12	0.49803 (13)	0.1175 (3)	0.10742 (13)	0.0448 (5)
C13	0.36708 (19)	−0.0598 (4)	0.21911 (14)	0.0796 (9)
H13A	0.3348	0.0366	0.2227	0.119*
H13B	0.3819	−0.1120	0.2645	0.119*
H13C	0.3366	−0.1364	0.1860	0.119*
C14	0.31198 (18)	0.3251 (4)	−0.09904 (14)	0.0695 (8)
H14A	0.2806	0.2278	−0.0946	0.104*
H14B	0.3117	0.3450	−0.1480	0.104*
H14C	0.2891	0.4190	−0.0797	0.104*
C15	0.20540 (11)	0.4688 (3)	0.18954 (10)	0.0353 (4)
C16	0.16481 (12)	0.4150 (3)	0.24222 (10)	0.0387 (5)
C17	0.13494 (13)	0.5310 (3)	0.28312 (12)	0.0479 (5)
H17	0.1091	0.4955	0.3185	0.057*
C18	0.14315 (14)	0.6992 (3)	0.27181 (13)	0.0516 (6)
H18	0.1228	0.7758	0.2996	0.062*
C19	0.18119 (13)	0.7540 (3)	0.21972 (12)	0.0482 (5)
H19	0.1862	0.8670	0.2118	0.058*
C20	0.21190 (13)	0.6384 (3)	0.17919 (11)	0.0416 (5)
H20	0.2376	0.6755	0.1440	0.050*
C21	0.24280 (12)	0.3527 (3)	0.14442 (11)	0.0405 (4)
C22	0.1085 (2)	0.1952 (4)	0.29900 (16)	0.0758 (8)
H22A	0.1299	0.2374	0.3454	0.114*
H22B	0.1076	0.0761	0.3004	0.114*
H22C	0.0545	0.2361	0.2828	0.114*
C23	0.13813 (11)	−0.2080 (3)	−0.02853 (10)	0.0351 (4)
C24	0.05986 (12)	−0.1656 (3)	−0.06558 (10)	0.0384 (5)
C25	0.00480 (13)	−0.2911 (3)	−0.09126 (12)	0.0495 (6)
H25	−0.0467	−0.2638	−0.1161	0.059*
C26	0.02634 (15)	−0.4555 (3)	−0.07995 (13)	0.0562 (6)
H26	−0.0107	−0.5380	−0.0978	0.067*
C27	0.10208 (15)	−0.4998 (3)	−0.04248 (12)	0.0519 (6)
H27	0.1160	−0.6109	−0.0346	0.062*
C28	0.15693 (13)	−0.3753 (3)	−0.01683 (11)	0.0422 (5)
H28	0.2077	−0.4043	0.0089	0.051*
C29	0.20123 (11)	−0.0812 (3)	0.00066 (10)	0.0345 (4)
C30	−0.03947 (14)	0.0418 (4)	−0.10615 (14)	0.0611 (7)
H30A	−0.0494	0.0086	−0.1548	0.092*
H30B	−0.0465	0.1597	−0.1033	0.092*
H30C	−0.0768	−0.0138	−0.0828	0.092*

	U11	U22	U33	U12	U13	U23
O1	0.0453 (7)	0.0492 (6)	0.0427 (9)	0.0018 (6)	0.0146 (7)	−0.0052 (6)
O2	0.0472 (8)	0.0521 (7)	0.0521 (9)	−0.0004 (6)	0.0172 (7)	−0.0110 (7)
O1'	0.0453 (7)	0.0492 (6)	0.0427 (9)	0.0018 (6)	0.0146 (7)	−0.0052 (6)
O2'	0.0472 (8)	0.0521 (7)	0.0521 (9)	−0.0004 (6)	0.0172 (7)	−0.0110 (7)
Cd1	0.02953 (8)	0.04385 (9)	0.03711 (8)	−0.00541 (6)	0.00932 (6)	−0.00570 (6)
O3	0.0769 (11)	0.0434 (9)	0.0519 (9)	−0.0021 (8)	0.0286 (8)	0.0021 (7)
O4	0.0421 (8)	0.0463 (9)	0.0512 (9)	−0.0114 (7)	−0.0027 (7)	0.0072 (7)
O5	0.0435 (8)	0.0485 (9)	0.0412 (8)	−0.0067 (7)	−0.0027 (7)	0.0022 (6)
O6	0.0338 (7)	0.0507 (9)	0.0547 (9)	0.0001 (7)	0.0029 (6)	0.0011 (7)
N1	0.0392 (9)	0.0404 (9)	0.0450 (10)	−0.0038 (8)	0.0015 (8)	−0.0075 (8)
N2	0.0408 (9)	0.0401 (9)	0.0438 (9)	−0.0072 (8)	0.0170 (8)	−0.0088 (8)
C1	0.0659 (15)	0.0497 (14)	0.0444 (13)	−0.0037 (12)	−0.0096 (11)	−0.0048 (11)
C2	0.0766 (19)	0.0648 (17)	0.0639 (17)	0.0070 (15)	−0.0215 (15)	−0.0022 (14)
C3	0.0603 (16)	0.0705 (18)	0.084 (2)	0.0167 (15)	−0.0292 (15)	−0.0167 (16)
C4	0.0367 (12)	0.0559 (14)	0.0887 (19)	0.0029 (11)	−0.0017 (12)	−0.0290 (14)
C5	0.0339 (13)	0.077 (2)	0.130 (3)	0.0012 (13)	0.0076 (16)	−0.0381 (19)
C6	0.0363 (12)	0.0722 (18)	0.137 (3)	−0.0151 (12)	0.0415 (15)	−0.0456 (19)
C7	0.0500 (12)	0.0493 (13)	0.0879 (17)	−0.0141 (11)	0.0403 (12)	−0.0275 (13)
C8	0.0705 (16)	0.0641 (17)	0.101 (2)	−0.0256 (13)	0.0593 (16)	−0.0288 (15)
C9	0.099 (2)	0.0605 (16)	0.0643 (16)	−0.0215 (15)	0.0495 (16)	−0.0069 (13)
C10	0.0627 (14)	0.0468 (12)	0.0520 (13)	−0.0112 (11)	0.0243 (11)	−0.0067 (11)
C11	0.0339 (10)	0.0379 (11)	0.0653 (14)	−0.0075 (9)	0.0198 (10)	−0.0226 (10)
C12	0.0342 (10)	0.0397 (11)	0.0579 (13)	−0.0007 (9)	0.0039 (10)	−0.0179 (10)
C13	0.089 (2)	0.096 (2)	0.0483 (14)	−0.0276 (18)	0.0030 (14)	0.0169 (15)
C14	0.0814 (19)	0.0728 (18)	0.0538 (15)	−0.0059 (15)	0.0128 (14)	0.0141 (13)
C15	0.0286 (9)	0.0458 (11)	0.0301 (9)	0.0018 (8)	0.0026 (7)	−0.0014 (8)
C16	0.0364 (10)	0.0446 (11)	0.0347 (10)	0.0004 (9)	0.0065 (8)	0.0014 (9)
C17	0.0482 (12)	0.0548 (14)	0.0460 (12)	0.0004 (10)	0.0220 (10)	−0.0021 (10)
C18	0.0496 (12)	0.0521 (13)	0.0566 (13)	0.0092 (11)	0.0192 (11)	−0.0078 (11)
C19	0.0484 (12)	0.0401 (12)	0.0558 (13)	0.0055 (10)	0.0103 (10)	0.0040 (10)
C20	0.0373 (11)	0.0501 (12)	0.0376 (11)	−0.0003 (9)	0.0080 (9)	0.0049 (9)
C21	0.0389 (7)	0.0452 (7)	0.0374 (7)	0.0038 (5)	0.0080 (5)	−0.0022 (5)
C22	0.105 (2)	0.0601 (16)	0.0738 (18)	−0.0175 (16)	0.0444 (17)	0.0048 (14)
C23	0.0340 (9)	0.0429 (11)	0.0308 (9)	−0.0057 (9)	0.0121 (8)	−0.0045 (8)
C24	0.0349 (10)	0.0487 (12)	0.0339 (10)	−0.0069 (9)	0.0123 (8)	−0.0047 (9)
C25	0.0380 (11)	0.0634 (15)	0.0467 (12)	−0.0119 (11)	0.0080 (9)	−0.0099 (11)
C26	0.0549 (13)	0.0560 (15)	0.0600 (14)	−0.0227 (11)	0.0170 (11)	−0.0167 (12)
C27	0.0642 (14)	0.0415 (12)	0.0551 (13)	−0.0086 (11)	0.0242 (11)	−0.0073 (10)
C28	0.0433 (11)	0.0467 (12)	0.0395 (11)	−0.0021 (9)	0.0151 (9)	−0.0047 (9)
C29	0.0293 (9)	0.0435 (11)	0.0324 (9)	−0.0020 (8)	0.0107 (8)	−0.0041 (8)
C30	0.0420 (12)	0.0708 (17)	0.0654 (16)	0.0091 (12)	−0.0007 (11)	−0.0055 (13)

O1—C21	1.266 (3)	C8—H8	0.9300
O1—Cd1	2.416 (3)	C9—C10	1.424 (4)
O2—C21	1.245 (3)	C9—H9	0.9300
O2—Cd1	2.336 (3)	C10—C14	1.495 (4)
O1'—C21	1.254 (4)	C11—C12	1.443 (3)
O1'—Cd1	2.299 (5)	C13—H13A	0.9600
O2'—C21	1.314 (4)	C13—H13B	0.9600
O2'—Cd1	2.331 (4)	C13—H13C	0.9600
Cd1—O5	2.3184 (15)	C14—H14A	0.9600
Cd1—O4	2.3207 (14)	C14—H14B	0.9600
Cd1—N2	2.3435 (16)	C14—H14C	0.9600
Cd1—N1	2.3444 (17)	C15—C20	1.388 (3)
Cd1—C29	2.660 (2)	C15—C16	1.410 (3)
Cd1—C21	2.691 (2)	C15—C21	1.505 (3)
O3—C16	1.361 (3)	C16—C17	1.385 (3)
O3—C22	1.430 (3)	C17—C18	1.384 (3)
O4—C29	1.258 (3)	C17—H17	0.9300
O5—C29	1.262 (2)	C18—C19	1.376 (3)
O6—C24	1.359 (3)	C18—H18	0.9300
O6—C30	1.429 (3)	C19—C20	1.385 (3)
N1—C1	1.335 (3)	C19—H19	0.9300
N1—C12	1.359 (3)	C20—H20	0.9300
N2—C10	1.328 (3)	C22—H22A	0.9600
N2—C11	1.370 (3)	C22—H22B	0.9600
C1—C2	1.399 (4)	C22—H22C	0.9600
C1—C13	1.495 (4)	C23—C28	1.392 (3)
C2—C3	1.355 (5)	C23—C24	1.411 (3)
C2—H2	0.9300	C23—C29	1.501 (3)
C3—C4	1.401 (4)	C24—C25	1.395 (3)
C3—H3	0.9300	C25—C26	1.378 (4)
C4—C12	1.419 (3)	C25—H25	0.9300
C4—C5	1.421 (4)	C26—C27	1.382 (3)
C5—C6	1.336 (5)	C26—H26	0.9300
C5—H5	0.9300	C27—C28	1.387 (3)
C6—C7	1.444 (4)	C27—H27	0.9300
C6—H6	0.9300	C28—H28	0.9300
C7—C8	1.389 (4)	C30—H30A	0.9600
C7—C11	1.415 (3)	C30—H30B	0.9600
C8—C9	1.358 (4)	C30—H30C	0.9600
C21—O1—Cd1	88.12 (18)	C7—C11—C12	118.7 (2)
C21—O2—Cd1	92.34 (17)	N1—C12—C4	121.1 (2)
C21—O1'—Cd1	93.8 (3)	N1—C12—C11	118.83 (18)
C21—O2'—Cd1	90.8 (2)	C4—C12—C11	120.0 (2)
O1'—Cd1—O5	142.22 (10)	C1—C13—H13A	109.5
O1'—Cd1—O4	112.12 (12)	C1—C13—H13B	109.5
O5—Cd1—O4	56.39 (5)	H13A—C13—H13B	109.5
O1'—Cd1—O2'	56.84 (12)	C1—C13—H13C	109.5
O5—Cd1—O2'	87.78 (10)	H13A—C13—H13C	109.5
O4—Cd1—O2'	99.14 (12)	H13B—C13—H13C	109.5
O5—Cd1—O2	88.74 (8)	C10—C14—H14A	109.5
O4—Cd1—O2	86.75 (8)	C10—C14—H14B	109.5
O1'—Cd1—N2	95.65 (10)	H14A—C14—H14B	109.5
O5—Cd1—N2	121.61 (6)	C10—C14—H14C	109.5
O4—Cd1—N2	104.02 (6)	H14A—C14—H14C	109.5
O2'—Cd1—N2	149.50 (10)	H14B—C14—H14C	109.5
O2—Cd1—N2	148.95 (8)	C20—C15—C16	118.13 (19)
O1'—Cd1—N1	102.91 (12)	C20—C15—C21	118.20 (18)
O5—Cd1—N1	94.91 (6)	C16—C15—C21	123.67 (19)
O4—Cd1—N1	144.97 (6)	O3—C16—C17	122.47 (19)
O2'—Cd1—N1	99.26 (12)	O3—C16—C15	117.81 (18)
O2—Cd1—N1	114.69 (9)	C17—C16—C15	119.7 (2)
N2—Cd1—N1	72.33 (6)	C18—C17—C16	120.6 (2)
O5—Cd1—O1	143.18 (8)	C18—C17—H17	119.7
O4—Cd1—O1	121.99 (8)	C16—C17—H17	119.7
O2—Cd1—O1	55.52 (9)	C19—C18—C17	120.5 (2)
N2—Cd1—O1	95.04 (8)	C19—C18—H18	119.8
N1—Cd1—O1	92.96 (8)	C17—C18—H18	119.8
O1'—Cd1—C29	129.77 (11)	C18—C19—C20	119.1 (2)
O2'—Cd1—C29	91.94 (11)	C18—C19—H19	120.5
O2—Cd1—C29	85.42 (8)	C20—C19—H19	120.5
N2—Cd1—C29	117.66 (6)	C19—C20—C15	122.0 (2)
N1—Cd1—C29	121.76 (6)	C19—C20—H20	119.0
O1—Cd1—C29	137.15 (8)	C15—C20—H20	119.0
O1'—Cd1—C21	27.70 (10)	O2—C21—O1'	113.5 (3)
O5—Cd1—C21	115.59 (6)	O2—C21—O1	123.7 (3)
O4—Cd1—C21	106.35 (6)	O1'—C21—O2'	118.2 (3)
O2—Cd1—C21	27.53 (8)	O1—C21—O2'	117.8 (3)
N2—Cd1—C21	122.80 (6)	O2—C21—C15	119.3 (2)
N1—Cd1—C21	104.26 (6)	O1'—C21—C15	121.7 (3)
C29—Cd1—C21	111.87 (6)	O1—C21—C15	116.7 (2)
C16—O3—C22	117.27 (19)	O2'—C21—C15	119.9 (2)
C29—O4—Cd1	91.07 (11)	O2—C21—Cd1	60.13 (15)
C29—O5—Cd1	91.08 (12)	O1'—C21—Cd1	58.5 (2)
C24—O6—C30	117.56 (18)	O1—C21—Cd1	63.82 (17)
C1—N1—C12	120.2 (2)	O2'—C21—Cd1	60.0 (2)
C1—N1—Cd1	124.78 (16)	C15—C21—Cd1	179.11 (14)
C12—N1—Cd1	114.99 (14)	O3—C22—H22A	109.5
C10—N2—C11	119.51 (19)	O3—C22—H22B	109.5
C10—N2—Cd1	126.00 (15)	H22A—C22—H22B	109.5
C11—N2—Cd1	114.41 (14)	O3—C22—H22C	109.5
N1—C1—C2	121.0 (3)	H22A—C22—H22C	109.5
N1—C1—C13	117.6 (2)	H22B—C22—H22C	109.5
C2—C1—C13	121.4 (3)	C28—C23—C24	118.41 (18)
C3—C2—C1	119.9 (3)	C28—C23—C29	118.45 (18)
C3—C2—H2	120.0	C24—C23—C29	123.11 (19)
C1—C2—H2	120.0	O6—C24—C25	123.07 (19)
C2—C3—C4	120.5 (2)	O6—C24—C23	117.39 (17)
C2—C3—H3	119.8	C25—C24—C23	119.5 (2)
C4—C3—H3	119.8	C26—C25—C24	120.3 (2)
C3—C4—C12	117.2 (3)	C26—C25—H25	119.9
C3—C4—C5	123.5 (3)	C24—C25—H25	119.9
C12—C4—C5	119.3 (3)	C25—C26—C27	121.2 (2)
C6—C5—C4	121.1 (3)	C25—C26—H26	119.4
C6—C5—H5	119.5	C27—C26—H26	119.4
C4—C5—H5	119.5	C26—C27—C28	118.7 (2)
C5—C6—C7	122.0 (3)	C26—C27—H27	120.7
C5—C6—H6	119.0	C28—C27—H27	120.7
C7—C6—H6	119.0	C27—C28—C23	121.9 (2)
C8—C7—C11	117.3 (2)	C27—C28—H28	119.1
C8—C7—C6	123.9 (2)	C23—C28—H28	119.1
C11—C7—C6	118.9 (3)	O4—C29—O5	120.88 (18)
C9—C8—C7	120.5 (2)	O4—C29—C23	121.38 (17)
C9—C8—H8	119.8	O5—C29—C23	117.70 (18)
C7—C8—H8	119.8	O4—C29—Cd1	60.71 (10)
C8—C9—C10	120.1 (3)	O5—C29—Cd1	60.61 (10)
C8—C9—H9	120.0	C23—C29—Cd1	175.00 (13)
C10—C9—H9	120.0	O6—C30—H30A	109.5
N2—C10—C9	120.6 (2)	O6—C30—H30B	109.5
N2—C10—C14	118.2 (2)	H30A—C30—H30B	109.5
C9—C10—C14	121.2 (2)	O6—C30—H30C	109.5
N2—C11—C7	122.1 (2)	H30A—C30—H30C	109.5
N2—C11—C12	119.18 (18)	H30B—C30—H30C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O5i	0.93	2.46	3.312 (3)	152
C17—H17···O6ii	0.93	2.60	3.487 (3)	161
C14—H14A···O4	0.96	2.45	3.322 (3)	150
C6—H6···O5iii	0.93	2.55	3.206 (3)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O5i	0.93	2.46	3.312 (3)	152
C17—H17⋯O6ii	0.93	2.60	3.487 (3)	161
C14—H14A⋯O4	0.96	2.45	3.322 (3)	150
C6—H6⋯O5iii	0.93	2.55	3.206 (3)	128

Symmetry codes: (i) ; (ii) ; (iii) .