catena-Poly[[[bis­(1,10-phenanthroline)cadmium(II)]-μ-naphthalene-2,6-dicarboxyl­ato] monohydrate]

The title cadmium coordination polymer, {[Cd(C₁₂H₆O₄)(C₁₂H₈N₂)₂]·H₂O}_n, has been synthesized and characterized by single-crystal X-ray diffraction. Each Cd^II cation is coordinated by two carboxyl­ate O atoms belonging to two NDC anions (NDC is naphthalene-2,6-dicarboxyl­ate) and four N atoms from two phen ligands (phen is 1,10-phenanthroline). Each NDC anion bridges two Cd^II cations through the two terminal carb­oxylate groups in a monodentate fashion to form a zigzag polymeric chain and there are π–π inter­actions between adjacent chains. The title coordination polymer exhibits an extended three-dimensional network feature based on inter­chain hydrogen bonding and and π–π stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.027
• wR factor = 0.069
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.20
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13    ..  O2      ..       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8     ..  O3      ..       2.65 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97.

catena-Poly[[[bis(1,10-phenanthroline)cadmium(II)]- µ-naphthalene-2,6-dicarboxylato] monohydrate]

Crystal data

[Cd(C12H6O4)(C12H8N2)2]·H2O	F(000) = 1424
Mr = 704.99	Dx = 1.622 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 24977 reflections
a = 12.413 (4) Å	θ = 3.1–27.5°
b = 18.573 (5) Å	µ = 0.81 mm^−1
c = 12.555 (4) Å	T = 293 K
β = 93.970 (14)°	Block, colourless
V = 2887.5 (15) Å^3	0.44 × 0.33 × 0.22 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	6582 independent reflections
Radiation source: fine-focus sealed tube	5812 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 10.0 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −16→16
Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995)	k = −23→24
Tmin = 0.718, Tmax = 0.841	l = −16→16
27995 measured reflections

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0323P)^2 + 1.3871P] where P = (Fo^2 + 2Fc^2)/3
6582 reflections	(Δ/σ)max = 0.001
423 parameters	Δρmax = 0.82 e Å^−3
0 restraints	Δρmin = −0.26 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
Cd1	0.933644 (8)	0.160431 (5)	0.304600 (7)	0.02655 (2)
O1	0.76857 (9)	0.12334 (6)	0.34826 (9)	0.0454 (3)
O2	0.86603 (9)	0.09038 (8)	0.49272 (11)	0.0558 (4)
O3	0.93851 (10)	0.26421 (6)	0.39955 (10)	0.0463 (3)
O4	0.84335 (13)	0.31436 (7)	0.26491 (11)	0.0659 (4)
O1W	0.63569 (12)	0.23879 (10)	0.27572 (14)	0.0733 (5)
N1	1.10388 (10)	0.14133 (6)	0.40011 (10)	0.0319 (3)
N2	1.08037 (10)	0.20635 (7)	0.20460 (9)	0.0319 (3)
N3	0.96202 (10)	0.03797 (6)	0.23902 (10)	0.0322 (3)
N4	0.84552 (10)	0.14209 (6)	0.12763 (9)	0.0310 (3)
C1	1.11414 (14)	0.11649 (9)	0.49933 (13)	0.0410 (4)
H1	1.0524	0.1023	0.5317	0.080*
C2	1.21413 (15)	0.11071 (9)	0.55731 (14)	0.0465 (4)
H2	1.2184	0.0941	0.6273	0.080*
C3	1.30507 (14)	0.12979 (9)	0.50969 (15)	0.0459 (4)
H3	1.3722	0.1256	0.5469	0.080*
C4	1.29753 (13)	0.15562 (8)	0.40498 (15)	0.0401 (4)
C5	1.38936 (13)	0.17844 (10)	0.35059 (18)	0.0522 (5)
H5	1.4580	0.1735	0.3844	0.080*
C6	1.37862 (14)	0.20670 (10)	0.25219 (18)	0.0543 (5)
H6	1.4399	0.2199	0.2183	0.080*
C7	1.27404 (13)	0.21694 (8)	0.19829 (14)	0.0415 (4)
C8	1.25880 (15)	0.24950 (10)	0.09757 (15)	0.0504 (4)
H8	1.3180	0.2631	0.0607	0.080*
C9	1.15628 (16)	0.26107 (9)	0.05415 (14)	0.0478 (4)
H9	1.1448	0.2831	−0.0122	0.080*
C10	1.06917 (14)	0.23939 (8)	0.11091 (13)	0.0400 (4)
H10	0.9997	0.2486	0.0815	0.080*
C11	1.18111 (11)	0.19492 (7)	0.24863 (12)	0.0318 (3)
C12	1.19351 (12)	0.16188 (7)	0.35297 (12)	0.0316 (3)
C13	1.01679 (14)	−0.01308 (8)	0.29290 (13)	0.0409 (4)
H13	1.0518	−0.0012	0.3584	0.080*
C14	1.02466 (16)	−0.08383 (9)	0.25634 (15)	0.0492 (5)
H14	1.0637	−0.1180	0.2970	0.080*
C15	0.97438 (16)	−0.10192 (9)	0.16041 (16)	0.0504 (5)
H15	0.9782	−0.1488	0.1350	0.080*
C16	0.91677 (14)	−0.04942 (8)	0.10023 (13)	0.0409 (4)
C17	0.86159 (17)	−0.06426 (10)	−0.00184 (16)	0.0545 (5)
H17	0.8645	−0.1104	−0.0302	0.080*
C18	0.80614 (16)	−0.01313 (11)	−0.05685 (14)	0.0537 (5)
H18	0.7719	−0.0243	−0.1230	0.080*
C19	0.79858 (13)	0.05857 (9)	−0.01571 (12)	0.0405 (4)
C20	0.73627 (15)	0.11233 (11)	−0.06797 (13)	0.0493 (5)
H20	0.7011	0.1032	−0.1344	0.080*
C21	0.72724 (15)	0.17767 (10)	−0.02165 (15)	0.0500 (5)
H21	0.6840	0.2132	−0.0546	0.080*
C22	0.78398 (14)	0.19092 (8)	0.07655 (13)	0.0410 (4)
H22	0.7782	0.2362	0.1074	0.080*
C23	0.85181 (11)	0.07558 (8)	0.08401 (11)	0.0308 (3)
C24	0.91247 (11)	0.02051 (8)	0.14317 (11)	0.0314 (3)
C25	0.67611 (12)	0.04376 (9)	0.58941 (12)	0.0373 (4)
H25	0.7346	0.0550	0.6368	0.080*
C26	0.68000 (11)	0.06023 (7)	0.48014 (12)	0.0313 (3)
C27	0.59402 (12)	0.04365 (8)	0.41056 (11)	0.0319 (3)
H27	0.5961	0.0561	0.3390	0.080*
C28	0.50195 (11)	0.00808 (7)	0.44500 (11)	0.0298 (3)
C29	0.41286 (13)	−0.01142 (9)	0.37386 (12)	0.0376 (4)
H29	0.4151	−0.0020	0.3013	0.080*
C30	0.77980 (12)	0.09368 (8)	0.43866 (13)	0.0352 (3)
C31	1.11277 (15)	0.54561 (9)	0.65911 (13)	0.0439 (4)
H31	1.1568	0.5507	0.7216	0.080*
C32	1.08540 (15)	0.47850 (9)	0.62376 (13)	0.0427 (4)
H32	1.1115	0.4383	0.6614	0.080*
C33	1.01738 (12)	0.46978 (8)	0.52996 (11)	0.0335 (3)
C34	0.98575 (13)	0.39966 (8)	0.49033 (12)	0.0374 (4)
H34	1.0078	0.3591	0.5293	0.080*
C35	0.92455 (12)	0.39142 (8)	0.39752 (12)	0.0351 (3)
C36	0.89867 (13)	0.31754 (8)	0.35040 (12)	0.0370 (4)
H1WA	0.6863 (19)	0.2660 (13)	0.2694 (19)	0.074 (7)*
H1WB	0.672 (2)	0.2021 (17)	0.289 (2)	0.107 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cd1	0.02563 (5)	0.02620 (5)	0.02809 (5)	−0.00442 (4)	0.00391 (4)	−0.00199 (4)
O1	0.0386 (6)	0.0476 (6)	0.0515 (6)	−0.0089 (5)	0.0146 (5)	0.0101 (5)
O2	0.0296 (5)	0.0677 (8)	0.0700 (8)	−0.0119 (6)	0.0020 (6)	0.0106 (7)
O3	0.0579 (7)	0.0304 (5)	0.0508 (6)	−0.0011 (5)	0.0062 (6)	−0.0096 (5)
O4	0.0949 (10)	0.0508 (7)	0.0486 (7)	−0.0238 (7)	−0.0201 (7)	−0.0071 (6)
O1W	0.0400 (7)	0.0869 (11)	0.0935 (11)	0.0067 (7)	0.0083 (7)	0.0032 (9)
N1	0.0303 (6)	0.0317 (6)	0.0334 (6)	−0.0029 (5)	0.0001 (5)	−0.0014 (5)
N2	0.0321 (6)	0.0303 (6)	0.0338 (6)	−0.0050 (5)	0.0055 (5)	−0.0007 (5)
N3	0.0360 (6)	0.0274 (5)	0.0334 (6)	−0.0013 (5)	0.0037 (5)	−0.0007 (5)
N4	0.0348 (6)	0.0270 (5)	0.0313 (6)	−0.0043 (5)	0.0028 (5)	0.0016 (5)
C1	0.0423 (8)	0.0429 (8)	0.0370 (7)	−0.0026 (7)	−0.0026 (7)	0.0021 (7)
C2	0.0521 (9)	0.0427 (8)	0.0429 (8)	0.0037 (7)	−0.0106 (7)	0.0002 (7)
C3	0.0392 (8)	0.0372 (8)	0.0585 (10)	0.0065 (7)	−0.0158 (7)	−0.0069 (7)
C4	0.0295 (7)	0.0307 (7)	0.0592 (10)	0.0015 (6)	−0.0030 (7)	−0.0078 (7)
C5	0.0259 (7)	0.0472 (9)	0.0831 (13)	0.0002 (7)	0.0006 (8)	−0.0047 (9)
C6	0.0295 (7)	0.0489 (9)	0.0865 (13)	−0.0048 (7)	0.0181 (8)	−0.0035 (9)
C7	0.0352 (7)	0.0328 (7)	0.0582 (9)	−0.0054 (6)	0.0146 (7)	−0.0048 (7)
C8	0.0508 (9)	0.0429 (8)	0.0608 (10)	−0.0108 (7)	0.0267 (8)	0.0030 (8)
C9	0.0605 (10)	0.0381 (8)	0.0463 (9)	−0.0075 (8)	0.0152 (8)	0.0075 (7)
C10	0.0448 (8)	0.0365 (8)	0.0391 (8)	−0.0065 (7)	0.0063 (7)	0.0038 (6)
C11	0.0303 (6)	0.0242 (6)	0.0418 (7)	−0.0038 (5)	0.0080 (6)	−0.0065 (6)
C12	0.0293 (6)	0.0245 (6)	0.0410 (7)	−0.0020 (5)	0.0015 (6)	−0.0070 (5)
C13	0.0488 (9)	0.0336 (7)	0.0404 (8)	0.0019 (7)	0.0037 (7)	0.0044 (6)
C14	0.0581 (10)	0.0326 (7)	0.0573 (10)	0.0069 (7)	0.0071 (8)	0.0068 (7)
C15	0.0592 (10)	0.0286 (7)	0.0645 (11)	0.0006 (7)	0.0115 (9)	−0.0070 (7)
C16	0.0428 (8)	0.0328 (7)	0.0477 (8)	−0.0032 (6)	0.0077 (7)	−0.0087 (7)
C17	0.0625 (11)	0.0437 (9)	0.0571 (10)	−0.0049 (8)	0.0019 (9)	−0.0241 (8)
C18	0.0567 (10)	0.0588 (10)	0.0447 (9)	−0.0100 (9)	−0.0036 (8)	−0.0214 (8)
C19	0.0385 (8)	0.0465 (8)	0.0364 (7)	−0.0090 (7)	0.0012 (6)	−0.0041 (7)
C20	0.0489 (9)	0.0602 (10)	0.0374 (8)	−0.0127 (8)	−0.0073 (7)	0.0051 (8)
C21	0.0506 (9)	0.0461 (9)	0.0514 (9)	−0.0079 (8)	−0.0105 (8)	0.0171 (8)
C22	0.0439 (8)	0.0322 (7)	0.0464 (8)	−0.0042 (7)	−0.0011 (7)	0.0080 (7)
C23	0.0299 (6)	0.0320 (7)	0.0310 (6)	−0.0063 (5)	0.0054 (5)	−0.0018 (5)
C24	0.0311 (6)	0.0290 (6)	0.0348 (7)	−0.0054 (5)	0.0069 (5)	−0.0038 (6)
C25	0.0328 (7)	0.0403 (8)	0.0386 (7)	−0.0077 (6)	0.0015 (6)	0.0004 (6)
C26	0.0292 (6)	0.0260 (6)	0.0397 (7)	−0.0031 (5)	0.0092 (6)	−0.0002 (6)
C27	0.0326 (7)	0.0302 (6)	0.0338 (7)	−0.0028 (6)	0.0090 (6)	0.0036 (6)
C28	0.0296 (6)	0.0273 (6)	0.0333 (7)	−0.0027 (5)	0.0070 (5)	0.0025 (5)
C29	0.0369 (7)	0.0445 (8)	0.0318 (7)	−0.0072 (7)	0.0048 (6)	0.0036 (6)
C30	0.0333 (7)	0.0261 (6)	0.0478 (8)	−0.0047 (5)	0.0137 (6)	−0.0035 (6)
C31	0.0528 (9)	0.0396 (8)	0.0385 (8)	−0.0035 (7)	−0.0030 (7)	−0.0053 (7)
C32	0.0537 (9)	0.0366 (8)	0.0363 (7)	0.0015 (7)	−0.0075 (7)	−0.0015 (6)
C33	0.0354 (7)	0.0356 (7)	0.0297 (6)	0.0005 (6)	0.0033 (6)	0.0014 (6)
C34	0.0402 (8)	0.0348 (7)	0.0377 (7)	−0.0008 (6)	0.0048 (6)	−0.0050 (6)
C35	0.0357 (7)	0.0327 (7)	0.0379 (7)	−0.0067 (6)	0.0087 (6)	−0.0111 (6)
C36	0.0415 (8)	0.0331 (7)	0.0374 (7)	−0.0134 (6)	0.0088 (6)	−0.0104 (6)

Geometric parameters (Å, º)

Cd1—O1	2.2648 (13)	C13—H13	0.9300
Cd1—O3	2.2649 (12)	C14—C15	1.360 (3)
Cd1—N1	2.3829 (14)	C14—H14	0.9300
Cd1—N4	2.4316 (13)	C15—C16	1.399 (2)
Cd1—N2	2.4367 (13)	C15—H15	0.9300
Cd1—N3	2.4526 (13)	C16—C24	1.409 (2)
O1—C30	1.2606 (19)	C16—C17	1.437 (2)
O2—C30	1.2286 (19)	C17—C18	1.337 (3)
O3—C36	1.251 (2)	C17—H17	0.9300
O4—C36	1.235 (2)	C18—C19	1.434 (3)
O1W—H1WA	0.81 (2)	C18—H18	0.9300
O1W—H1WB	0.83 (3)	C19—C20	1.398 (3)
N1—C1	1.326 (2)	C19—C23	1.410 (2)
N1—C12	1.351 (2)	C20—C21	1.354 (3)
N2—C10	1.325 (2)	C20—H20	0.9300
N2—C11	1.3486 (19)	C21—C22	1.399 (2)
N3—C13	1.325 (2)	C21—H21	0.9300
N3—C24	1.3524 (19)	C22—H22	0.9300
N4—C22	1.323 (2)	C23—C24	1.445 (2)
N4—C23	1.3556 (18)	C25—C29^i	1.365 (2)
C1—C2	1.399 (2)	C25—C26	1.410 (2)
C1—H1	0.9300	C25—H25	0.9300
C2—C3	1.361 (3)	C26—C27	1.367 (2)
C2—H2	0.9300	C26—C30	1.510 (2)
C3—C4	1.396 (3)	C27—C28	1.413 (2)
C3—H3	0.9300	C27—H27	0.9300
C4—C12	1.411 (2)	C28—C28^i	1.417 (3)
C4—C5	1.433 (3)	C28—C29	1.420 (2)
C5—C6	1.340 (3)	C29—C25^i	1.365 (2)
C5—H5	0.9300	C29—H29	0.9300
C6—C7	1.434 (2)	C31—C32	1.358 (2)
C6—H6	0.9300	C31—C35^ii	1.429 (2)
C7—C8	1.403 (3)	C31—H31	0.9300
C7—C11	1.414 (2)	C32—C33	1.410 (2)
C8—C9	1.366 (3)	C32—H32	0.9300
C8—H8	0.9300	C33—C33^ii	1.403 (3)
C9—C10	1.395 (2)	C33—C34	1.439 (2)
C9—H9	0.9300	C34—C35	1.355 (2)
C10—H10	0.9300	C34—H34	0.9300
C11—C12	1.445 (2)	C35—C31^ii	1.429 (2)
C13—C14	1.397 (2)	C35—C36	1.520 (2)
O1—Cd1—O3	97.07 (5)	C15—C14—C13	119.02 (16)
O1—Cd1—N1	128.21 (5)	C15—C14—H14	120.5
O3—Cd1—N1	82.61 (4)	C13—C14—H14	120.5
O1—Cd1—N4	79.70 (5)	C14—C15—C16	119.47 (15)
O3—Cd1—N4	126.45 (4)	C14—C15—H15	120.3
N1—Cd1—N4	140.00 (4)	C16—C15—H15	120.3
O1—Cd1—N2	162.22 (4)	C15—C16—C24	117.86 (15)
O3—Cd1—N2	88.84 (5)	C15—C16—C17	122.81 (15)
N1—Cd1—N2	69.08 (5)	C24—C16—C17	119.32 (15)
N4—Cd1—N2	83.29 (5)	C18—C17—C16	121.40 (16)
O1—Cd1—N3	87.28 (4)	C18—C17—H17	119.3
O3—Cd1—N3	165.16 (4)	C16—C17—H17	119.3
N1—Cd1—N3	83.56 (4)	C17—C18—C19	121.19 (16)
N4—Cd1—N3	68.24 (4)	C17—C18—H18	119.4
N2—Cd1—N3	91.25 (4)	C19—C18—H18	119.4
C30—O1—Cd1	107.78 (10)	C20—C19—C23	117.81 (15)
C36—O3—Cd1	114.77 (10)	C20—C19—C18	122.82 (15)
H1WA—O1W—H1WB	97 (3)	C23—C19—C18	119.31 (15)
C1—N1—C12	118.77 (13)	C21—C20—C19	119.87 (16)
C1—N1—Cd1	123.27 (11)	C21—C20—H20	120.1
C12—N1—Cd1	117.77 (10)	C19—C20—H20	120.1
C10—N2—C11	118.30 (13)	C20—C21—C22	119.00 (16)
C10—N2—Cd1	125.67 (10)	C20—C21—H21	120.5
C11—N2—Cd1	116.02 (9)	C22—C21—H21	120.5
C13—N3—C24	117.94 (13)	N4—C22—C21	123.04 (15)
C13—N3—Cd1	124.95 (10)	N4—C22—H22	118.5
C24—N3—Cd1	117.00 (9)	C21—C22—H22	118.5
C22—N4—C23	118.46 (13)	N4—C23—C19	121.74 (13)
C22—N4—Cd1	123.72 (10)	N4—C23—C24	118.68 (12)
C23—N4—Cd1	117.51 (9)	C19—C23—C24	119.56 (13)
N1—C1—C2	122.65 (16)	N3—C24—C16	122.32 (13)
N1—C1—H1	118.7	N3—C24—C23	118.46 (12)
C2—C1—H1	118.7	C16—C24—C23	119.22 (13)
C3—C2—C1	118.99 (16)	C29^i—C25—C26	120.48 (14)
C3—C2—H2	120.5	C29^i—C25—H25	119.8
C1—C2—H2	120.5	C26—C25—H25	119.8
C2—C3—C4	119.97 (15)	C27—C26—C25	119.69 (13)
C2—C3—H3	120.0	C27—C26—C30	119.68 (13)
C4—C3—H3	120.0	C25—C26—C30	120.60 (13)
C3—C4—C12	117.62 (15)	C26—C27—C28	121.46 (13)
C3—C4—C5	123.13 (16)	C26—C27—H27	119.3
C12—C4—C5	119.20 (16)	C28—C27—H27	119.3
C6—C5—C4	121.56 (16)	C27—C28—C28^i	118.68 (16)
C6—C5—H5	119.2	C27—C28—C29	122.55 (13)
C4—C5—H5	119.2	C28^i—C28—C29	118.77 (16)
C5—C6—C7	121.05 (17)	C25^i—C29—C28	120.86 (14)
C5—C6—H6	119.5	C25^i—C29—H29	119.6
C7—C6—H6	119.5	C28—C29—H29	119.6
C8—C7—C11	117.68 (15)	O2—C30—O1	123.84 (15)
C8—C7—C6	122.94 (16)	O2—C30—C26	119.54 (14)
C11—C7—C6	119.37 (16)	O1—C30—C26	116.61 (13)
C9—C8—C7	119.42 (16)	C32—C31—C35^ii	121.55 (15)
C9—C8—H8	120.3	C32—C31—H31	119.2
C7—C8—H8	120.3	C35^ii—C31—H31	119.2
C8—C9—C10	118.97 (16)	C31—C32—C33	120.00 (15)
C8—C9—H9	120.5	C31—C32—H32	120.0
C10—C9—H9	120.5	C33—C32—H32	120.0
N2—C10—C9	123.34 (16)	C33^ii—C33—C32	120.00 (17)
N2—C10—H10	118.3	C33^ii—C33—C34	118.20 (16)
C9—C10—H10	118.3	C32—C33—C34	121.73 (14)
N2—C11—C7	122.23 (14)	C35—C34—C33	121.52 (14)
N2—C11—C12	118.42 (13)	C35—C34—H34	119.2
C7—C11—C12	119.29 (14)	C33—C34—H34	119.2
N1—C12—C4	121.94 (14)	C34—C35—C31^ii	118.59 (14)
N1—C12—C11	118.55 (13)	C34—C35—C36	121.84 (14)
C4—C12—C11	119.42 (14)	C31^ii—C35—C36	119.52 (13)
N3—C13—C14	123.39 (15)	O4—C36—O3	124.61 (15)
N3—C13—H13	118.3	O4—C36—C35	118.13 (14)
C14—C13—H13	118.3	O3—C36—C35	117.21 (14)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2^iii	0.93	2.65	3.298 (2)	127.6
C6—H6···O1W^iv	0.93	2.51	3.240 (3)	135.4
C8—H8···O3^v	0.93	2.65	3.463 (2)	146.8
C1—H1···O2	0.93	2.34	3.113 (2)	140
C22—H22···O4	0.93	2.54	3.339 (2)	144
O1W—H1WB···O1	0.83 (3)	2.00 (3)	2.818 (2)	169 (3)
O1W—H1WA···O4	0.81 (2)	2.15 (2)	2.946 (2)	166 (2)

Symmetry codes: (iii) −x+2, −y, −z+1; (iv) x+1, y, z; (v) x+1/2, −y+1/2, z−1/2.