Aqua-(dicyanamido-κN)(2,9-dimethyl-1,10-phenanthroline-κN,N')(nitrato-κO,O')cobalt(II)-2,9-dimethyl-1,10-phenanthroline-water (2/1/2).

In the title compound, 2[Co(C(2)N(3))(NO(3))(C(14)H(12)N(2))(H(2)O)]·C(14)H(12)N(2)·2H(2)O, the Co(II) ion is coordinated by a bidentate 2,9-dimethyl-1,10-phenanthroline (dmphen) ligand, a bidentate nitrate anion, a water mol-ecule and a monodentate dicyan-amide group in a distorted octa-hedral geometry. One uncoordinated dmphen mol-ecule is situated on a crystallographic twofold axis and the asymmetric unit is completed by one water mol-ecule. In the crystal, mol-ecules form a one-dimensional framework in the [001] direction through O-H⋯N and O-H⋯O hydrogen bonds. The crystal packing is further stabilized by π-π stacking inter-actions between the dmphen rings of neighboring mol-ecules, with a centroid-centroid separation of 3.5641 (8) Å and a partially overlapped arrangement of parallel dmphen rings with a distance of 3.407 (2) Å.

Related literature

For background to metal–phenanthroline complexes, see: Naing et al. (1995 ▶); Wang et al. (1996 ▶); Wall et al. (1999 ▶). For related Co(II)–phenanthroline structures, see: Ding et al. (2006 ▶); Xuan & Zhao (2007 ▶); Zhao et al. (2008 ▶).

Experimental

Crystal data

2[Co(C2N3)(NO3)(C14H12N2)(H2O)]·C14H12N2·2H2O

M = 1070.82

Monoclinic,

a = 17.993 (6) Å

b = 11.770 (4) Å

c = 23.428 (7) Å

β = 106.981 (4)°

V = 4745 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.77 mm−1

T = 291 K

0.34 × 0.18 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.781, T max = 0.917

17592 measured reflections

4400 independent reflections

2862 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.196

S = 1.04

4400 reflections

328 parameters

36 restraints

H-atom parameters constrained

Δρmax = 1.06 e Å−3

Δρmin = −0.58 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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/S1600536811035148/bh2369sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035148/bh2369Isup2.hkl

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

2[Co(C2N3)(NO3)(C14H12N2)(H2O)]·C14H12N2·2H2O	F(000) = 2208
Mr = 1070.82	Dx = 1.499 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2628 reflections
a = 17.993 (6) Å	θ = 2.4–21.2°
b = 11.770 (4) Å	µ = 0.77 mm−1
c = 23.428 (7) Å	T = 291 K
β = 106.981 (4)°	Block, pink
V = 4745 (3) Å3	0.34 × 0.18 × 0.11 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4400 independent reflections
Radiation source: fine-focus sealed tube	2862 reflections with I > 2σ(I)
graphite	Rint = 0.070
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −21→21
Tmin = 0.781, Tmax = 0.917	k = −13→14
17592 measured reflections	l = −28→28

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1026P)2 + 4.8562P] where P = (Fo2 + 2Fc2)/3
4400 reflections	(Δ/σ)max < 0.001
328 parameters	Δρmax = 1.06 e Å−3
36 restraints	Δρmin = −0.58 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Co1	0.42687 (4)	0.19148 (5)	0.38145 (3)	0.0453 (3)
O1	0.3472 (2)	0.0602 (3)	0.32847 (17)	0.0706 (10)
O2	0.3720 (3)	−0.1178 (3)	0.3477 (2)	0.1070 (17)
O3	0.4528 (2)	0.0107 (3)	0.39358 (17)	0.0648 (10)
O4	0.4792 (3)	0.1851 (3)	0.31525 (17)	0.0672 (11)
H1W	0.4450	0.1747	0.2819	0.101*
H2W	0.5124	0.2344	0.3124	0.101*
O5	0.5612 (6)	−0.0066 (7)	0.2802 (4)	0.233 (5)
H3W	0.5731	0.0572	0.2975	0.350*
H4W	0.5602	−0.0359	0.3132	0.350*
N1	0.5202 (2)	0.2867 (3)	0.43700 (16)	0.0443 (9)
N2	0.3892 (2)	0.3599 (3)	0.35623 (16)	0.0434 (9)
N3	0.3653 (3)	0.1776 (4)	0.4424 (2)	0.0694 (13)
N4	0.2925 (4)	0.1214 (6)	0.5087 (3)	0.114 (2)
N5	0.3362 (7)	0.1052 (7)	0.6164 (4)	0.172 (4)
N6	0.3906 (3)	−0.0181 (4)	0.3558 (2)	0.0667 (12)
N7	0.5696 (2)	0.3653 (4)	0.29332 (18)	0.0534 (10)
C1	0.5844 (3)	0.2489 (5)	0.4772 (2)	0.0568 (13)
C2	0.6423 (3)	0.3248 (7)	0.5087 (3)	0.0753 (18)
H2	0.6866	0.2966	0.5363	0.090*
C3	0.6345 (3)	0.4380 (6)	0.4995 (3)	0.0701 (16)
H3	0.6737	0.4871	0.5200	0.084*
C4	0.5662 (3)	0.4812 (5)	0.4582 (2)	0.0582 (14)
C5	0.5522 (4)	0.5994 (5)	0.4464 (3)	0.0696 (16)
H5	0.5887	0.6522	0.4669	0.084*
C6	0.4872 (4)	0.6351 (5)	0.4062 (3)	0.0694 (16)
H6	0.4793	0.7125	0.3991	0.083*
C7	0.4299 (3)	0.5567 (4)	0.3738 (2)	0.0534 (13)
C8	0.3608 (4)	0.5883 (4)	0.3314 (3)	0.0639 (15)
H8	0.3504	0.6647	0.3226	0.077*
C9	0.3089 (3)	0.5090 (5)	0.3029 (3)	0.0651 (15)
H9	0.2633	0.5308	0.2745	0.078*
C10	0.3242 (3)	0.3931 (4)	0.3164 (2)	0.0504 (12)
C11	0.4419 (3)	0.4398 (4)	0.38500 (19)	0.0433 (11)
C12	0.5111 (3)	0.4015 (4)	0.4278 (2)	0.0455 (11)
C13	0.5937 (4)	0.1235 (5)	0.4881 (3)	0.0800 (18)
H13A	0.5582	0.0983	0.5091	0.120*
H13B	0.6460	0.1073	0.5115	0.120*
H13C	0.5827	0.0844	0.4505	0.120*
C14	0.2674 (3)	0.3042 (5)	0.2860 (3)	0.0705 (16)
H14A	0.2920	0.2521	0.2658	0.106*
H14B	0.2240	0.3394	0.2576	0.106*
H14C	0.2495	0.2638	0.3151	0.106*
C15	0.3341 (4)	0.1530 (5)	0.4758 (3)	0.0691 (16)
C16	0.3184 (6)	0.1179 (7)	0.5646 (5)	0.110 (3)
C17	0.6397 (4)	0.3631 (7)	0.3335 (3)	0.0808 (18)
C18	0.6784 (4)	0.4641 (8)	0.3554 (3)	0.099 (2)
H18	0.7274	0.4612	0.3830	0.118*
C19	0.6457 (5)	0.5651 (8)	0.3371 (3)	0.101 (2)
H19	0.6712	0.6315	0.3534	0.121*
C20	0.5729 (5)	0.5711 (6)	0.2933 (3)	0.0904 (19)
C21	0.5337 (5)	0.6744 (6)	0.2707 (4)	0.105 (3)
H21	0.5565	0.7433	0.2856	0.127*
C22	0.5374 (3)	0.4659 (4)	0.2729 (2)	0.0542 (13)
C23	0.6749 (4)	0.2515 (8)	0.3539 (3)	0.111 (3)
H23A	0.6522	0.1949	0.3245	0.167*
H23B	0.6655	0.2320	0.3910	0.167*
H23C	0.7299	0.2550	0.3595	0.167*

	U11	U22	U33	U12	U13	U23
Co1	0.0533 (5)	0.0302 (4)	0.0530 (4)	−0.0039 (3)	0.0165 (3)	−0.0007 (3)
O1	0.075 (3)	0.048 (2)	0.079 (3)	−0.002 (2)	0.007 (2)	0.0021 (19)
O2	0.133 (4)	0.035 (2)	0.144 (4)	−0.020 (2)	0.026 (3)	−0.015 (2)
O3	0.070 (3)	0.043 (2)	0.078 (2)	−0.0033 (18)	0.017 (2)	0.0042 (17)
O4	0.104 (3)	0.041 (2)	0.071 (2)	−0.0056 (19)	0.048 (2)	−0.0030 (16)
O5	0.371 (15)	0.145 (7)	0.204 (9)	−0.066 (8)	0.118 (9)	−0.001 (6)
N1	0.047 (2)	0.040 (2)	0.047 (2)	−0.0035 (17)	0.0147 (18)	0.0012 (16)
N2	0.047 (2)	0.035 (2)	0.051 (2)	−0.0026 (18)	0.0189 (19)	−0.0007 (17)
N3	0.078 (3)	0.060 (3)	0.082 (3)	−0.016 (2)	0.041 (3)	−0.010 (2)
N4	0.129 (5)	0.110 (5)	0.136 (5)	−0.022 (4)	0.092 (5)	−0.001 (4)
N5	0.295 (11)	0.124 (7)	0.147 (7)	−0.022 (7)	0.141 (8)	−0.015 (5)
N6	0.084 (4)	0.032 (3)	0.082 (3)	−0.010 (2)	0.022 (3)	−0.004 (2)
N7	0.043 (2)	0.062 (3)	0.058 (2)	−0.001 (2)	0.020 (2)	−0.004 (2)
C1	0.054 (3)	0.064 (3)	0.051 (3)	−0.004 (3)	0.014 (2)	0.001 (3)
C2	0.049 (3)	0.112 (6)	0.059 (3)	−0.008 (3)	0.007 (3)	−0.003 (3)
C3	0.055 (3)	0.078 (4)	0.075 (4)	−0.022 (3)	0.017 (3)	−0.017 (3)
C4	0.060 (3)	0.057 (3)	0.064 (3)	−0.023 (3)	0.028 (3)	−0.017 (3)
C5	0.082 (4)	0.050 (3)	0.083 (4)	−0.032 (3)	0.034 (4)	−0.026 (3)
C6	0.097 (5)	0.037 (3)	0.087 (4)	−0.015 (3)	0.048 (4)	−0.013 (3)
C7	0.071 (4)	0.030 (2)	0.069 (3)	−0.001 (2)	0.036 (3)	−0.006 (2)
C8	0.085 (4)	0.034 (3)	0.081 (4)	0.015 (3)	0.037 (3)	0.009 (3)
C9	0.066 (4)	0.054 (3)	0.076 (4)	0.016 (3)	0.021 (3)	0.008 (3)
C10	0.057 (3)	0.042 (3)	0.053 (3)	0.006 (2)	0.017 (2)	0.002 (2)
C11	0.052 (3)	0.034 (2)	0.050 (3)	−0.005 (2)	0.023 (2)	−0.0062 (19)
C12	0.050 (3)	0.041 (3)	0.052 (3)	−0.009 (2)	0.025 (2)	−0.007 (2)
C13	0.078 (4)	0.073 (4)	0.078 (4)	0.012 (3)	0.007 (3)	0.021 (3)
C14	0.061 (4)	0.066 (4)	0.074 (4)	−0.002 (3)	0.003 (3)	−0.001 (3)
C15	0.079 (4)	0.045 (3)	0.098 (4)	−0.009 (3)	0.049 (4)	−0.010 (3)
C16	0.160 (6)	0.081 (5)	0.128 (6)	−0.018 (4)	0.105 (6)	−0.018 (5)
C17	0.054 (4)	0.130 (6)	0.065 (3)	−0.010 (4)	0.028 (3)	−0.011 (4)
C18	0.066 (4)	0.145 (6)	0.088 (4)	−0.038 (4)	0.028 (3)	−0.032 (4)
C19	0.096 (5)	0.118 (5)	0.106 (5)	−0.066 (4)	0.057 (4)	−0.047 (4)
C20	0.114 (5)	0.072 (4)	0.112 (5)	−0.040 (4)	0.075 (4)	−0.027 (3)
C21	0.152 (7)	0.053 (3)	0.139 (7)	−0.025 (4)	0.085 (5)	−0.023 (4)
C22	0.061 (3)	0.046 (3)	0.071 (3)	−0.014 (2)	0.043 (3)	−0.012 (2)
C23	0.073 (5)	0.174 (8)	0.084 (5)	0.046 (5)	0.019 (4)	0.030 (5)

Co1—O4	2.037 (4)	C5—H5	0.9300
Co1—N3	2.053 (5)	C6—C7	1.425 (8)
Co1—N1	2.120 (4)	C6—H6	0.9300
Co1—N2	2.122 (4)	C7—C8	1.397 (7)
Co1—O3	2.180 (4)	C7—C11	1.405 (7)
Co1—O1	2.224 (4)	C8—C9	1.350 (8)
O1—N6	1.256 (6)	C8—H8	0.9300
O2—N6	1.220 (5)	C9—C10	1.408 (7)
O3—N6	1.253 (6)	C9—H9	0.9300
O4—H1W	0.8501	C10—C14	1.491 (7)
O4—H2W	0.8500	C11—C12	1.425 (7)
O5—H3W	0.8500	C13—H13A	0.9600
O5—H4W	0.8501	C13—H13B	0.9600
N1—C1	1.336 (6)	C13—H13C	0.9600
N1—C12	1.371 (6)	C14—H14A	0.9600
N2—C10	1.325 (6)	C14—H14B	0.9600
N2—C11	1.366 (6)	C14—H14C	0.9600
N3—C15	1.126 (7)	C17—C18	1.398 (10)
N4—C16	1.256 (11)	C17—C23	1.476 (11)
N4—C15	1.276 (8)	C18—C19	1.339 (11)
N5—C16	1.172 (11)	C18—H18	0.9300
N7—C17	1.336 (7)	C19—C20	1.410 (11)
N7—C22	1.344 (7)	C19—H19	0.9300
C1—C2	1.406 (8)	C20—C22	1.411 (8)
C1—C13	1.499 (8)	C20—C21	1.427 (10)
C2—C3	1.349 (9)	C21—C21i	1.314 (17)
C2—H2	0.9300	C21—H21	0.9300
C3—C4	1.419 (8)	C22—C22i	1.455 (11)
C3—H3	0.9300	C23—H23A	0.9600
C4—C12	1.398 (7)	C23—H23B	0.9600
C4—C5	1.426 (8)	C23—H23C	0.9600
C5—C6	1.337 (9)
O4—Co1—N3	171.71 (16)	C9—C8—C7	120.8 (5)
O4—Co1—N1	91.57 (16)	C9—C8—H8	119.6
N3—Co1—N1	96.13 (17)	C7—C8—H8	119.6
O4—Co1—N2	90.19 (14)	C8—C9—C10	119.8 (5)
N3—Co1—N2	94.27 (17)	C8—C9—H9	120.1
N1—Co1—N2	78.95 (14)	C10—C9—H9	120.1
O4—Co1—O3	86.23 (14)	N2—C10—C9	121.2 (5)
N3—Co1—O3	88.30 (17)	N2—C10—C14	118.1 (4)
N1—Co1—O3	109.58 (15)	C9—C10—C14	120.7 (5)
N2—Co1—O3	170.81 (15)	N2—C11—C7	122.4 (4)
O4—Co1—O1	85.13 (16)	N2—C11—C12	117.9 (4)
N3—Co1—O1	86.69 (17)	C7—C11—C12	119.7 (4)
N1—Co1—O1	167.45 (15)	N1—C12—C4	123.1 (5)
N2—Co1—O1	113.10 (14)	N1—C12—C11	117.5 (4)
O3—Co1—O1	58.18 (14)	C4—C12—C11	119.3 (5)
N6—O1—Co1	91.2 (3)	C1—C13—H13A	109.5
N6—O3—Co1	93.4 (3)	C1—C13—H13B	109.5
Co1—O4—H1W	109.6	H13A—C13—H13B	109.5
Co1—O4—H2W	121.9	C1—C13—H13C	109.5
H1W—O4—H2W	111.2	H13A—C13—H13C	109.5
H3W—O5—H4W	89.8	H13B—C13—H13C	109.5
C1—N1—C12	118.6 (4)	C10—C14—H14A	109.5
C1—N1—Co1	128.6 (3)	C10—C14—H14B	109.5
C12—N1—Co1	112.8 (3)	H14A—C14—H14B	109.5
C10—N2—C11	119.2 (4)	C10—C14—H14C	109.5
C10—N2—Co1	128.1 (3)	H14A—C14—H14C	109.5
C11—N2—Co1	112.8 (3)	H14B—C14—H14C	109.5
C15—N3—Co1	169.5 (5)	N3—C15—N4	173.6 (8)
C16—N4—C15	122.4 (8)	N5—C16—N4	172.3 (10)
O2—N6—O3	121.2 (5)	N7—C17—C18	120.5 (7)
O2—N6—O1	121.6 (5)	N7—C17—C23	118.3 (7)
O3—N6—O1	117.1 (4)	C18—C17—C23	121.2 (7)
C17—N7—C22	119.3 (5)	C19—C18—C17	120.9 (7)
N1—C1—C2	120.9 (5)	C19—C18—H18	119.6
N1—C1—C13	118.5 (5)	C17—C18—H18	119.6
C2—C1—C13	120.6 (5)	C18—C19—C20	120.3 (7)
C3—C2—C1	121.1 (6)	C18—C19—H19	119.8
C3—C2—H2	119.4	C20—C19—H19	119.8
C1—C2—H2	119.4	C19—C20—C22	115.8 (7)
C2—C3—C4	119.4 (5)	C19—C20—C21	124.5 (7)
C2—C3—H3	120.3	C22—C20—C21	119.7 (7)
C4—C3—H3	120.3	C21i—C21—C20	121.6 (4)
C12—C4—C3	116.8 (5)	C21i—C21—H21	119.2
C12—C4—C5	119.8 (5)	C20—C21—H21	119.2
C3—C4—C5	123.4 (5)	N7—C22—C20	123.2 (6)
C6—C5—C4	120.8 (5)	N7—C22—C22i	118.2 (3)
C6—C5—H5	119.6	C20—C22—C22i	118.7 (4)
C4—C5—H5	119.6	C17—C23—H23A	109.5
C5—C6—C7	121.3 (5)	C17—C23—H23B	109.5
C5—C6—H6	119.4	H23A—C23—H23B	109.5
C7—C6—H6	119.4	C17—C23—H23C	109.5
C8—C7—C11	116.7 (5)	H23A—C23—H23C	109.5
C8—C7—C6	124.2 (5)	H23B—C23—H23C	109.5
C11—C7—C6	119.1 (5)
O4—Co1—O1—N6	90.4 (3)	C5—C6—C7—C8	179.8 (5)
N3—Co1—O1—N6	−88.2 (3)	C5—C6—C7—C11	0.5 (8)
N1—Co1—O1—N6	15.2 (8)	C11—C7—C8—C9	−0.1 (8)
N2—Co1—O1—N6	178.5 (3)	C6—C7—C8—C9	−179.5 (5)
O3—Co1—O1—N6	1.8 (3)	C7—C8—C9—C10	0.5 (8)
O4—Co1—O3—N6	−88.4 (3)	C11—N2—C10—C9	0.6 (7)
N3—Co1—O3—N6	85.3 (3)	Co1—N2—C10—C9	−177.4 (4)
N1—Co1—O3—N6	−178.8 (3)	C11—N2—C10—C14	−179.6 (4)
O1—Co1—O3—N6	−1.8 (3)	Co1—N2—C10—C14	2.4 (7)
O4—Co1—N1—C1	−90.8 (4)	C8—C9—C10—N2	−0.8 (8)
N3—Co1—N1—C1	86.1 (4)	C8—C9—C10—C14	179.3 (5)
N2—Co1—N1—C1	179.3 (4)	C10—N2—C11—C7	−0.1 (6)
O3—Co1—N1—C1	−4.3 (4)	Co1—N2—C11—C7	178.2 (3)
O1—Co1—N1—C1	−16.3 (9)	C10—N2—C11—C12	179.8 (4)
O4—Co1—N1—C12	87.9 (3)	Co1—N2—C11—C12	−1.9 (5)
N3—Co1—N1—C12	−95.2 (3)	C8—C7—C11—N2	−0.1 (7)
N2—Co1—N1—C12	−2.0 (3)	C6—C7—C11—N2	179.3 (4)
O3—Co1—N1—C12	174.4 (3)	C8—C7—C11—C12	180.0 (4)
O1—Co1—N1—C12	162.4 (6)	C6—C7—C11—C12	−0.6 (7)
O4—Co1—N2—C10	88.7 (4)	C1—N1—C12—C4	0.4 (7)
N3—Co1—N2—C10	−84.3 (4)	Co1—N1—C12—C4	−178.4 (4)
N1—Co1—N2—C10	−179.8 (4)	C1—N1—C12—C11	−179.5 (4)
O1—Co1—N2—C10	3.9 (4)	Co1—N1—C12—C11	1.7 (5)
O4—Co1—N2—C11	−89.4 (3)	C3—C4—C12—N1	1.1 (7)
N3—Co1—N2—C11	97.5 (3)	C5—C4—C12—N1	−179.5 (4)
N1—Co1—N2—C11	2.1 (3)	C3—C4—C12—C11	−179.0 (4)
O1—Co1—N2—C11	−174.2 (3)	C5—C4—C12—C11	0.4 (7)
N1—Co1—N3—C15	−113 (3)	N2—C11—C12—N1	0.2 (6)
N2—Co1—N3—C15	167 (3)	C7—C11—C12—N1	−179.9 (4)
O3—Co1—N3—C15	−4(3)	N2—C11—C12—C4	−179.7 (4)
O1—Co1—N3—C15	55 (3)	C7—C11—C12—C4	0.2 (6)
Co1—O3—N6—O2	−174.5 (5)	C22—N7—C17—C18	1.8 (8)
Co1—O3—N6—O1	3.1 (5)	C22—N7—C17—C23	−178.1 (5)
Co1—O1—N6—O2	174.5 (5)	N7—C17—C18—C19	0.8 (10)
Co1—O1—N6—O3	−3.0 (5)	C23—C17—C18—C19	−179.3 (6)
C12—N1—C1—C2	−1.2 (7)	C17—C18—C19—C20	−2.9 (11)
Co1—N1—C1—C2	177.4 (4)	C18—C19—C20—C22	2.4 (10)
C12—N1—C1—C13	178.9 (4)	C18—C19—C20—C21	−179.6 (7)
Co1—N1—C1—C13	−2.5 (7)	C19—C20—C21—C21i	179.3 (9)
N1—C1—C2—C3	0.4 (9)	C22—C20—C21—C21i	−2.8 (14)
C13—C1—C2—C3	−179.8 (6)	C17—N7—C22—C20	−2.2 (7)
C1—C2—C3—C4	1.2 (9)	C17—N7—C22—C22i	177.2 (5)
C2—C3—C4—C12	−1.9 (8)	C19—C20—C22—N7	0.1 (8)
C2—C3—C4—C5	178.8 (5)	C21—C20—C22—N7	−177.9 (6)
C12—C4—C5—C6	−0.5 (8)	C19—C20—C22—C22i	−179.3 (6)
C3—C4—C5—C6	178.8 (5)	C21—C20—C22—C22i	2.6 (9)
C4—C5—C6—C7	0.1 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1W···O5i	0.85	2.57	3.111 (9)	123.
O4—H2W···N7	0.85	1.97	2.810 (6)	167.
O5—H3W···O4	0.85	2.39	2.941 (11)	123.
O5—H4W···N5ii	0.85	2.25	2.830 (15)	126.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1W⋯O5i	0.85	2.57	3.111 (9)	123
O4—H2W⋯N7	0.85	1.97	2.810 (6)	167
O5—H4W⋯N5ii	0.85	2.25	2.830 (15)	126

Symmetry codes: (i) ; (ii) .