Honeycomb mol­ecular network based upon a hydrate of 4,6-di­chloro­resorcinol and the photoproduct rtct-tetra­kis­(pyridin-4-yl)cyclo­butane

The formation of a self-inter­penetrated honeycomb mol­ecular network based upon 4,6-di­chloro­resorcinol (4,6-diCl res), a water mol­ecule, and the photoproduct rtct-tetra­kis­(pyridin-4-yl)cyclo­butane (rtct-TPCB) is reported. Inter­estingly, only three of the four pyridine rings on the central cyclo­butane ring are found to engage in O—H...N hydrogen bonds with either the 4,6-diCl res or an included water mol­ecule, resulting in a three-connected net. Notably, the solid (4,6-diCl res)·(rtct-TPCB)·(H₂O), C₆H₄Cl₂O₂·C₂₄H₂₀N₄·H₂O, contains channels that run along the crystallographic b axis, which are found to be inter­penetrated. Although rtct-TPCB has been employed as a bridging ligand in the formation of numerous metal–organic materials, surprisingly neither the single-com­ponent X-ray structure nor any multi-com­ponent mol­ecular solids based upon this stereoisomer have been reported previously. Lastly, the single-crystal X-ray structure of the photoproduct rtct-TPCB is also reported.

Computing details

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2020); cell refinement: CrysAlis PRO (Rigaku OD, 2020); data reduction: CrysAlis PRO (Rigaku OD, 2020); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

rtct-1,2,3,4-Tetrakis(pyridin-4-yl)cyclobutane (rtct-TPCB)

Crystal data

C24H20N4	F(000) = 1536
Mr = 364.44	Dx = 1.256 Mg m^−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
a = 29.76986 (18) Å	Cell parameters from 28495 reflections
b = 8.91767 (4) Å	θ = 3.0–77.5°
c = 14.70912 (8) Å	µ = 0.59 mm^−1
β = 99.2973 (6)°	T = 100 K
V = 3853.65 (4) Å^3	Irregular, clear colourless
Z = 8	0.22 × 0.16 × 0.10 mm

Data collection

Rigaku XtaLAB Synergy diffractometer with a Dualflex HyPix detector	4044 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	3829 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.025
Detector resolution: 10.0000 pixels mm^-1	θmax = 77.6°, θmin = 3.0°
ω scans	h = −37→36
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2020)	k = −9→11
Tmin = 0.637, Tmax = 1.000	l = −18→18
36302 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[σ^2(Fo^2) + (0.0483P)^2 + 3.0424P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.102	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.28 e Å^−3
4044 reflections	Δρmin = −0.18 e Å^−3
254 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00036 (5)
Primary atom site location: dual

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. After data collection, the unit cell was redetermined using a subset of the full data collection. Intensity data were corrected for Lorentz, polarization, and background effects using CrysAlis PRO (Rigaku OD, 2020). A numerical absorption correction was applied based on a Gaussian integration over a multifaceted crystal and followed by a semi-empirical correction for adsorption applied using the program SCALE3 ABSPACK. The SHELX2014 (Sheldrick, 2015a and 2015b) series of programs was used for the solution and refinement of the crystal structure within the OLEX2 software (Dolomanov, et al., 2009).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.58182 (3)	0.03330 (11)	0.30232 (7)	0.0279 (2)
N2	0.66621 (4)	0.75045 (11)	0.61026 (7)	0.0296 (2)
N3	0.75637 (3)	0.81773 (12)	0.11522 (7)	0.0307 (2)
N4	0.49764 (4)	0.76001 (13)	−0.00233 (8)	0.0355 (3)
C1	0.60187 (3)	0.51203 (11)	0.28799 (7)	0.0186 (2)
H1	0.577099	0.564157	0.311374	0.022*
C2	0.64846 (3)	0.58069 (11)	0.33121 (7)	0.0183 (2)
H2	0.672862	0.509307	0.325412	0.022*
C3	0.64302 (3)	0.69217 (11)	0.24902 (7)	0.0188 (2)
H3	0.626866	0.782159	0.264249	0.023*
C4	0.60863 (3)	0.57984 (11)	0.19354 (7)	0.0185 (2)
H4	0.625468	0.508129	0.161410	0.022*
C5	0.59549 (3)	0.34542 (12)	0.29341 (7)	0.0195 (2)
C6	0.62072 (4)	0.25836 (13)	0.36157 (8)	0.0265 (2)
H6	0.642752	0.302138	0.405613	0.032*
C7	0.61267 (4)	0.10568 (13)	0.36310 (8)	0.0308 (3)
H7	0.629830	0.049484	0.409475	0.037*
C8	0.55861 (4)	0.11809 (13)	0.23584 (8)	0.0291 (3)
H8	0.537425	0.071061	0.191571	0.035*
C9	0.56413 (4)	0.27120 (13)	0.22881 (8)	0.0267 (2)
H9	0.546911	0.324311	0.181021	0.032*
C10	0.65462 (3)	0.64028 (11)	0.42789 (7)	0.0194 (2)
C11	0.69055 (4)	0.59309 (13)	0.49430 (7)	0.0246 (2)
H11	0.711396	0.523154	0.479525	0.030*
C12	0.69496 (4)	0.65139 (14)	0.58273 (8)	0.0292 (3)
H12	0.719514	0.619520	0.625677	0.035*
C13	0.63130 (4)	0.79322 (13)	0.54628 (8)	0.0274 (2)
H13	0.610408	0.860631	0.563643	0.033*
C14	0.62437 (4)	0.74333 (12)	0.45582 (7)	0.0233 (2)
H14	0.599756	0.778291	0.414143	0.028*
C15	0.68331 (3)	0.73617 (12)	0.20530 (7)	0.0205 (2)
C16	0.72717 (4)	0.68585 (13)	0.23572 (7)	0.0249 (2)
H16	0.733173	0.623288	0.286824	0.030*
C17	0.76219 (4)	0.72955 (14)	0.18928 (8)	0.0277 (2)
H17	0.791421	0.695126	0.211271	0.033*
C18	0.71389 (4)	0.86443 (17)	0.08580 (9)	0.0406 (3)
H18	0.708766	0.924966	0.033665	0.049*
C19	0.67703 (4)	0.82840 (15)	0.12803 (9)	0.0353 (3)
H19	0.648260	0.865570	0.104919	0.042*
C20	0.56938 (3)	0.64073 (11)	0.12696 (7)	0.0198 (2)
C21	0.56306 (4)	0.59993 (17)	0.03512 (8)	0.0348 (3)
H21	0.582631	0.531440	0.014215	0.042*
C22	0.52741 (5)	0.6616 (2)	−0.02566 (9)	0.0469 (4)
H22	0.524055	0.632129	−0.087040	0.056*
C23	0.50378 (4)	0.79856 (14)	0.08665 (9)	0.0330 (3)
H23	0.483585	0.866970	0.105560	0.040*
C24	0.53838 (4)	0.74291 (13)	0.15253 (8)	0.0299 (3)
H24	0.540851	0.773770	0.213529	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0305 (5)	0.0207 (5)	0.0312 (5)	−0.0036 (4)	0.0008 (4)	0.0010 (4)
N2	0.0392 (6)	0.0268 (5)	0.0226 (5)	−0.0013 (4)	0.0042 (4)	−0.0007 (4)
N3	0.0240 (5)	0.0420 (6)	0.0257 (5)	−0.0096 (4)	0.0027 (4)	0.0033 (4)
N4	0.0234 (5)	0.0478 (6)	0.0332 (5)	0.0024 (4)	−0.0020 (4)	0.0102 (5)
C1	0.0169 (4)	0.0187 (5)	0.0203 (5)	0.0001 (4)	0.0028 (4)	0.0001 (4)
C2	0.0172 (4)	0.0166 (5)	0.0209 (5)	0.0002 (4)	0.0026 (4)	0.0004 (4)
C3	0.0178 (5)	0.0174 (5)	0.0208 (5)	−0.0001 (4)	0.0014 (4)	0.0008 (4)
C4	0.0174 (5)	0.0171 (5)	0.0211 (5)	0.0002 (4)	0.0031 (4)	0.0000 (4)
C5	0.0182 (5)	0.0197 (5)	0.0212 (5)	−0.0010 (4)	0.0050 (4)	0.0004 (4)
C6	0.0285 (6)	0.0229 (6)	0.0254 (5)	−0.0032 (4)	−0.0038 (4)	0.0010 (4)
C7	0.0347 (6)	0.0229 (6)	0.0310 (6)	−0.0014 (5)	−0.0058 (5)	0.0046 (4)
C8	0.0291 (6)	0.0255 (6)	0.0299 (6)	−0.0065 (4)	−0.0038 (4)	−0.0002 (4)
C9	0.0250 (5)	0.0246 (6)	0.0277 (5)	−0.0026 (4)	−0.0037 (4)	0.0035 (4)
C10	0.0204 (5)	0.0168 (5)	0.0210 (5)	−0.0030 (4)	0.0035 (4)	0.0013 (4)
C11	0.0237 (5)	0.0251 (5)	0.0241 (5)	0.0025 (4)	0.0017 (4)	0.0007 (4)
C12	0.0315 (6)	0.0304 (6)	0.0235 (5)	0.0008 (5)	−0.0020 (4)	0.0018 (4)
C13	0.0342 (6)	0.0224 (5)	0.0266 (5)	0.0021 (4)	0.0080 (5)	−0.0012 (4)
C14	0.0243 (5)	0.0204 (5)	0.0248 (5)	0.0015 (4)	0.0029 (4)	0.0008 (4)
C15	0.0207 (5)	0.0193 (5)	0.0211 (5)	−0.0033 (4)	0.0023 (4)	−0.0011 (4)
C16	0.0215 (5)	0.0296 (6)	0.0226 (5)	−0.0017 (4)	0.0012 (4)	0.0041 (4)
C17	0.0203 (5)	0.0360 (6)	0.0265 (5)	−0.0029 (4)	0.0024 (4)	0.0016 (5)
C18	0.0271 (6)	0.0568 (9)	0.0369 (7)	−0.0071 (6)	0.0017 (5)	0.0229 (6)
C19	0.0219 (5)	0.0430 (7)	0.0399 (7)	−0.0014 (5)	0.0014 (5)	0.0193 (6)
C20	0.0182 (5)	0.0181 (5)	0.0226 (5)	−0.0026 (4)	0.0018 (4)	0.0021 (4)
C21	0.0241 (6)	0.0571 (8)	0.0232 (5)	0.0106 (5)	0.0036 (4)	−0.0024 (5)
C22	0.0293 (6)	0.0891 (12)	0.0214 (6)	0.0150 (7)	0.0020 (5)	0.0020 (6)
C23	0.0244 (6)	0.0262 (6)	0.0442 (7)	0.0045 (4)	−0.0068 (5)	−0.0050 (5)
C24	0.0269 (6)	0.0285 (6)	0.0311 (6)	0.0053 (5)	−0.0049 (5)	−0.0097 (5)

Geometric parameters (Å, º)

N1—C7	1.3394 (15)	C8—C9	1.3810 (16)
N1—C8	1.3369 (15)	C9—H9	0.9300
N2—C12	1.3376 (16)	C10—C11	1.3920 (14)
N2—C13	1.3398 (15)	C10—C14	1.3943 (15)
N3—C17	1.3320 (15)	C11—H11	0.9300
N3—C18	1.3355 (16)	C11—C12	1.3872 (15)
N4—C22	1.3311 (19)	C12—H12	0.9300
N4—C23	1.3369 (17)	C13—H13	0.9300
C1—H1	0.9800	C13—C14	1.3864 (15)
C1—C2	1.5548 (13)	C14—H14	0.9300
C1—C4	1.5576 (13)	C15—C16	1.3847 (15)
C1—C5	1.5017 (14)	C15—C19	1.3910 (15)
C2—H2	0.9800	C16—H16	0.9300
C2—C3	1.5533 (13)	C16—C17	1.3912 (15)
C2—C10	1.5013 (13)	C17—H17	0.9300
C3—H3	0.9800	C18—H18	0.9300
C3—C4	1.5646 (13)	C18—C19	1.3832 (17)
C3—C15	1.5017 (14)	C19—H19	0.9300
C4—H4	0.9800	C20—C21	1.3821 (15)
C4—C20	1.4998 (13)	C20—C24	1.3912 (15)
C5—C6	1.3888 (15)	C21—H21	0.9300
C5—C9	1.3878 (15)	C21—C22	1.3862 (17)
C6—H6	0.9300	C22—H22	0.9300
C6—C7	1.3833 (16)	C23—H23	0.9300
C7—H7	0.9300	C23—C24	1.3871 (16)
C8—H8	0.9300	C24—H24	0.9300
C8—N1—C7	115.68 (10)	C11—C10—C14	116.88 (9)
C12—N2—C13	115.91 (10)	C14—C10—C2	121.77 (9)
C17—N3—C18	116.13 (10)	C10—C11—H11	120.3
C22—N4—C23	115.50 (10)	C12—C11—C10	119.36 (10)
C2—C1—H1	110.0	C12—C11—H11	120.3
C2—C1—C4	88.67 (7)	N2—C12—C11	124.28 (11)
C4—C1—H1	110.0	N2—C12—H12	117.9
C5—C1—H1	110.0	C11—C12—H12	117.9
C5—C1—C2	118.69 (8)	N2—C13—H13	117.9
C5—C1—C4	117.85 (8)	N2—C13—C14	124.13 (11)
C1—C2—H2	109.5	C14—C13—H13	117.9
C3—C2—C1	87.70 (7)	C10—C14—H14	120.3
C3—C2—H2	109.5	C13—C14—C10	119.42 (10)
C10—C2—C1	119.42 (8)	C13—C14—H14	120.3
C10—C2—H2	109.5	C16—C15—C3	123.61 (9)
C10—C2—C3	119.48 (8)	C16—C15—C19	116.80 (10)
C2—C3—H3	109.8	C19—C15—C3	119.55 (9)
C2—C3—C4	88.47 (7)	C15—C16—H16	120.2
C4—C3—H3	109.8	C15—C16—C17	119.53 (10)
C15—C3—C2	120.70 (8)	C17—C16—H16	120.2
C15—C3—H3	109.8	N3—C17—C16	123.93 (10)
C15—C3—C4	116.40 (8)	N3—C17—H17	118.0
C1—C4—C3	87.21 (7)	C16—C17—H17	118.0
C1—C4—H4	109.1	N3—C18—H18	118.0
C3—C4—H4	109.1	N3—C18—C19	124.09 (11)
C20—C4—C1	121.59 (8)	C19—C18—H18	118.0
C20—C4—C3	118.95 (8)	C15—C19—H19	120.2
C20—C4—H4	109.1	C18—C19—C15	119.51 (11)
C6—C5—C1	122.22 (9)	C18—C19—H19	120.2
C9—C5—C1	120.83 (9)	C21—C20—C4	120.77 (10)
C9—C5—C6	116.95 (10)	C21—C20—C24	116.43 (10)
C5—C6—H6	120.4	C24—C20—C4	122.77 (9)
C7—C6—C5	119.14 (10)	C20—C21—H21	120.2
C7—C6—H6	120.4	C20—C21—C22	119.67 (12)
N1—C7—C6	124.43 (11)	C22—C21—H21	120.2
N1—C7—H7	117.8	N4—C22—C21	124.58 (12)
C6—C7—H7	117.8	N4—C22—H22	117.7
N1—C8—H8	118.0	C21—C22—H22	117.7
N1—C8—C9	124.07 (10)	N4—C23—H23	118.0
C9—C8—H8	118.0	N4—C23—C24	124.09 (11)
C5—C9—H9	120.2	C24—C23—H23	118.0
C8—C9—C5	119.69 (10)	C20—C24—H24	120.1
C8—C9—H9	120.2	C23—C24—C20	119.71 (11)
C11—C10—C2	121.35 (9)	C23—C24—H24	120.1
N1—C8—C9—C5	0.16 (19)	C4—C3—C15—C16	−107.03 (11)
N2—C13—C14—C10	1.08 (18)	C4—C3—C15—C19	70.73 (13)
N3—C18—C19—C15	−1.0 (2)	C4—C20—C21—C22	−177.86 (12)
N4—C23—C24—C20	0.2 (2)	C4—C20—C24—C23	177.78 (11)
C1—C2—C3—C4	−21.10 (7)	C5—C1—C2—C3	142.53 (9)
C1—C2—C3—C15	−141.20 (9)	C5—C1—C2—C10	−94.60 (11)
C1—C2—C10—C11	126.82 (10)	C5—C1—C4—C3	−143.11 (9)
C1—C2—C10—C14	−52.14 (13)	C5—C1—C4—C20	94.28 (11)
C1—C4—C20—C21	−131.47 (11)	C5—C6—C7—N1	0.3 (2)
C1—C4—C20—C24	50.33 (14)	C6—C5—C9—C8	1.45 (16)
C1—C5—C6—C7	179.20 (11)	C7—N1—C8—C9	−1.52 (18)
C1—C5—C9—C8	−179.39 (11)	C8—N1—C7—C6	1.29 (19)
C2—C1—C4—C3	−21.05 (7)	C9—C5—C6—C7	−1.65 (17)
C2—C1—C4—C20	−143.66 (9)	C10—C2—C3—C4	−143.92 (9)
C2—C1—C5—C6	24.81 (15)	C10—C2—C3—C15	95.98 (11)
C2—C1—C5—C9	−154.30 (10)	C10—C11—C12—N2	1.07 (18)
C2—C3—C4—C1	21.07 (7)	C11—C10—C14—C13	0.12 (15)
C2—C3—C4—C20	145.98 (9)	C12—N2—C13—C14	−1.16 (17)
C2—C3—C15—C16	−1.95 (15)	C13—N2—C12—C11	0.07 (18)
C2—C3—C15—C19	175.80 (10)	C14—C10—C11—C12	−1.11 (16)
C2—C10—C11—C12	179.88 (10)	C15—C3—C4—C1	144.91 (9)
C2—C10—C14—C13	179.13 (10)	C15—C3—C4—C20	−90.17 (11)
C3—C2—C10—C11	−127.76 (10)	C15—C16—C17—N3	−0.57 (19)
C3—C2—C10—C14	53.28 (13)	C16—C15—C19—C18	0.25 (19)
C3—C4—C20—C21	122.58 (11)	C17—N3—C18—C19	0.9 (2)
C3—C4—C20—C24	−55.62 (14)	C18—N3—C17—C16	−0.12 (19)
C3—C15—C16—C17	178.29 (10)	C19—C15—C16—C17	0.48 (17)
C3—C15—C19—C18	−177.66 (12)	C20—C21—C22—N4	−0.1 (2)
C4—C1—C2—C3	21.20 (7)	C21—C20—C24—C23	−0.50 (17)
C4—C1—C2—C10	144.07 (9)	C22—N4—C23—C24	0.1 (2)
C4—C1—C5—C6	129.83 (11)	C23—N4—C22—C21	−0.2 (2)
C4—C1—C5—C9	−49.28 (13)	C24—C20—C21—C22	0.45 (19)

rtct-1,2,3,4-Tetrakis(pyridin-4-yl)cyclobutane–4,6-dichlorobenzene-1,3-diol–water (1/1/1) (4_6-diCl_res.rtct-TPCB.H2O)

Crystal data

C24H20N4·C6H4Cl2O2·H2O	F(000) = 1168
Mr = 561.45	Dx = 1.410 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 13.8413 (1) Å	Cell parameters from 33543 reflections
b = 8.9901 (1) Å	θ = 3.3–77.6°
c = 21.8680 (2) Å	µ = 2.54 mm^−1
β = 103.683 (1)°	T = 100 K
V = 2643.91 (4) Å^3	Block, clear colourless
Z = 4	0.20 × 0.17 × 0.12 mm

Data collection

Rigaku XtaLAB Synergy diffractometer with a Dualflex HyPix detector	5515 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	5221 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.040
Detector resolution: 10.0000 pixels mm^-1	θmax = 77.6°, θmin = 3.3°
ω scans	h = −17→17
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2020)	k = −11→10
Tmin = 0.725, Tmax = 1.000	l = −27→27
50633 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.030	w = 1/[σ^2(Fo^2) + (0.0349P)^2 + 1.0984P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.078	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.34 e Å^−3
5515 reflections	Δρmin = −0.23 e Å^−3
358 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00041 (7)
Primary atom site location: dual

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. After data collection, the unit cell was redetermined using a subset of the full data collection. Intensity data were corrected for Lorentz, polarization, and background effects using CrysAlis PRO (Rigaku OD, 2020). A numerical absorption correction was applied based on a Gaussian integration over a multifaceted crystal and followed by a semi-empirical correction for adsorption applied using the program SCALE3 ABSPACK. The SHELX2014 (Sheldrick, 2015a and 2015b) series of programs was used for the solution and refinement of the crystal structure within the OLEX2 software (Dolomanov, et al., 2009).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.48683 (8)	0.55717 (13)	0.36301 (6)	0.0253 (2)
N2	1.04096 (8)	0.66590 (12)	0.46947 (5)	0.0211 (2)
N3	0.98935 (8)	0.52361 (12)	0.12458 (5)	0.0205 (2)
N4	0.72166 (8)	−0.19431 (12)	0.23706 (5)	0.0238 (2)
C7	0.74842 (8)	0.35508 (13)	0.32497 (5)	0.0158 (2)
H7	0.777509	0.287363	0.359542	0.019*
C8	0.82967 (8)	0.46610 (13)	0.31460 (5)	0.0153 (2)
H8	0.796929	0.548751	0.288522	0.018*
C9	0.86124 (8)	0.34871 (13)	0.27132 (5)	0.0155 (2)
H9	0.909097	0.279966	0.297019	0.019*
C10	0.75388 (8)	0.28237 (13)	0.26138 (5)	0.0160 (2)
H10	0.708458	0.333244	0.226462	0.019*
C11	0.65316 (9)	0.41745 (13)	0.33538 (6)	0.0169 (2)
C12	0.59631 (9)	0.51942 (14)	0.29389 (6)	0.0191 (2)
H12	0.612815	0.542909	0.256205	0.023*
C13	0.51491 (9)	0.58526 (15)	0.30955 (6)	0.0235 (3)
H13	0.477614	0.652819	0.281358	0.028*
C14	0.53928 (10)	0.45533 (15)	0.40149 (6)	0.0258 (3)
H14	0.519654	0.431528	0.438139	0.031*
C15	0.62148 (10)	0.38330 (14)	0.38957 (6)	0.0230 (3)
H15	0.655279	0.312513	0.417647	0.028*
C16	0.90404 (9)	0.52871 (13)	0.36999 (5)	0.0164 (2)
C17	1.00608 (9)	0.51130 (14)	0.37733 (5)	0.0194 (2)
H17	1.030444	0.453148	0.349162	0.023*
C18	1.07112 (9)	0.58132 (14)	0.42698 (6)	0.0215 (3)
H18	1.139054	0.569010	0.431024	0.026*
C19	0.94265 (9)	0.67943 (14)	0.46288 (6)	0.0211 (2)
H19	0.920320	0.736066	0.492367	0.025*
C20	0.87237 (9)	0.61406 (14)	0.41475 (6)	0.0195 (2)
H20	0.804895	0.626918	0.412307	0.023*
C21	0.90198 (8)	0.40407 (13)	0.21760 (5)	0.0154 (2)
C22	0.99160 (9)	0.34997 (14)	0.20828 (6)	0.0191 (2)
H22	1.024248	0.272588	0.232997	0.023*
C23	1.03181 (9)	0.41224 (14)	0.16190 (6)	0.0217 (3)
H23	1.091732	0.374437	0.156420	0.026*
C24	0.90181 (9)	0.57330 (14)	0.13259 (6)	0.0197 (2)
H24	0.870270	0.649277	0.106491	0.024*
C25	0.85564 (9)	0.51772 (14)	0.17763 (5)	0.0185 (2)
H25	0.794676	0.555583	0.181167	0.022*
C26	0.74232 (8)	0.11682 (13)	0.25362 (5)	0.0167 (2)
C27	0.71118 (9)	0.02747 (14)	0.29729 (6)	0.0195 (2)
H27	0.696712	0.069356	0.332980	0.023*
C28	0.70193 (9)	−0.12488 (14)	0.28701 (6)	0.0222 (3)
H28	0.680696	−0.182433	0.316669	0.027*
C29	0.75128 (10)	−0.10652 (15)	0.19532 (6)	0.0234 (3)
H29	0.765263	−0.151225	0.160039	0.028*
C30	0.76238 (9)	0.04626 (14)	0.20134 (6)	0.0200 (2)
H30	0.783047	0.101212	0.170715	0.024*
Cl1	0.50356 (2)	0.91759 (4)	0.37220 (2)	0.02473 (9)
Cl2	0.32412 (2)	1.33881 (3)	0.48080 (2)	0.02911 (9)
O1	0.37269 (7)	0.70483 (10)	0.42940 (5)	0.0270 (2)
H1	0.409306	0.690700	0.405462	0.040*
O2	0.22620 (7)	1.08906 (10)	0.52582 (4)	0.0242 (2)
H2	0.196131	1.017136	0.535095	0.036*
C1	0.41918 (9)	0.96317 (14)	0.41690 (5)	0.0190 (2)
C2	0.40607 (9)	1.11178 (14)	0.42942 (6)	0.0210 (2)
H2A	0.440806	1.184613	0.413281	0.025*
C3	0.34125 (9)	1.15176 (14)	0.46597 (6)	0.0201 (2)
C4	0.28827 (9)	1.04377 (14)	0.49048 (5)	0.0192 (2)
C5	0.30079 (9)	0.89574 (14)	0.47603 (6)	0.0193 (2)
H5	0.264373	0.823292	0.491077	0.023*
C6	0.36626 (9)	0.85203 (14)	0.43967 (6)	0.0189 (2)
O3	0.12788 (6)	0.87086 (10)	0.55989 (4)	0.02113 (18)
H3A	0.102475	0.805683	0.532673	0.032*
H3B	0.080836	0.895254	0.576823	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0200 (5)	0.0234 (6)	0.0359 (6)	−0.0041 (4)	0.0132 (5)	−0.0104 (5)
N2	0.0234 (5)	0.0206 (5)	0.0192 (5)	0.0012 (4)	0.0050 (4)	−0.0018 (4)
N3	0.0214 (5)	0.0225 (6)	0.0195 (5)	−0.0045 (4)	0.0089 (4)	−0.0025 (4)
N4	0.0258 (5)	0.0172 (5)	0.0292 (6)	0.0003 (4)	0.0081 (4)	−0.0015 (4)
C7	0.0172 (5)	0.0143 (5)	0.0174 (5)	0.0004 (4)	0.0068 (4)	0.0007 (4)
C8	0.0167 (5)	0.0146 (6)	0.0159 (5)	0.0005 (4)	0.0065 (4)	0.0001 (4)
C9	0.0159 (5)	0.0147 (6)	0.0170 (5)	0.0011 (4)	0.0057 (4)	0.0001 (4)
C10	0.0166 (5)	0.0153 (6)	0.0174 (5)	0.0011 (4)	0.0068 (4)	0.0000 (4)
C11	0.0178 (5)	0.0138 (6)	0.0209 (6)	−0.0027 (4)	0.0080 (4)	−0.0040 (4)
C12	0.0179 (5)	0.0197 (6)	0.0202 (6)	−0.0006 (4)	0.0056 (4)	−0.0040 (4)
C13	0.0182 (6)	0.0238 (7)	0.0280 (6)	0.0005 (5)	0.0045 (5)	−0.0072 (5)
C14	0.0293 (7)	0.0220 (7)	0.0327 (7)	−0.0068 (5)	0.0203 (6)	−0.0062 (5)
C15	0.0282 (6)	0.0188 (6)	0.0261 (6)	−0.0016 (5)	0.0143 (5)	0.0002 (5)
C16	0.0199 (6)	0.0140 (6)	0.0164 (5)	−0.0001 (4)	0.0067 (4)	0.0023 (4)
C17	0.0209 (6)	0.0196 (6)	0.0190 (6)	0.0023 (5)	0.0077 (5)	−0.0019 (4)
C18	0.0192 (6)	0.0238 (6)	0.0220 (6)	0.0022 (5)	0.0058 (5)	−0.0014 (5)
C19	0.0256 (6)	0.0195 (6)	0.0197 (6)	0.0031 (5)	0.0086 (5)	−0.0016 (5)
C20	0.0194 (6)	0.0203 (6)	0.0206 (6)	0.0023 (5)	0.0081 (5)	−0.0002 (5)
C21	0.0162 (5)	0.0155 (6)	0.0153 (5)	−0.0027 (4)	0.0052 (4)	−0.0030 (4)
C22	0.0186 (5)	0.0178 (6)	0.0220 (6)	0.0010 (4)	0.0069 (4)	−0.0013 (4)
C23	0.0199 (6)	0.0226 (6)	0.0252 (6)	−0.0002 (5)	0.0103 (5)	−0.0037 (5)
C24	0.0211 (6)	0.0208 (6)	0.0174 (5)	−0.0007 (5)	0.0052 (4)	0.0010 (4)
C25	0.0166 (5)	0.0204 (6)	0.0192 (5)	0.0012 (4)	0.0059 (4)	0.0001 (4)
C26	0.0134 (5)	0.0165 (6)	0.0199 (6)	0.0010 (4)	0.0036 (4)	0.0001 (4)
C27	0.0195 (6)	0.0190 (6)	0.0218 (6)	−0.0001 (5)	0.0085 (5)	−0.0005 (5)
C28	0.0229 (6)	0.0191 (6)	0.0266 (6)	−0.0015 (5)	0.0097 (5)	0.0018 (5)
C29	0.0266 (6)	0.0213 (6)	0.0237 (6)	0.0011 (5)	0.0083 (5)	−0.0032 (5)
C30	0.0215 (6)	0.0193 (6)	0.0205 (6)	0.0006 (5)	0.0074 (5)	0.0006 (5)
Cl1	0.02563 (16)	0.02632 (17)	0.02709 (16)	−0.00045 (11)	0.01592 (12)	−0.00316 (11)
Cl2	0.03560 (18)	0.01772 (16)	0.03833 (18)	−0.00042 (12)	0.01737 (14)	−0.00530 (12)
O1	0.0313 (5)	0.0188 (5)	0.0378 (5)	0.0010 (4)	0.0221 (4)	−0.0039 (4)
O2	0.0267 (5)	0.0202 (5)	0.0311 (5)	0.0015 (4)	0.0174 (4)	−0.0033 (4)
C1	0.0173 (5)	0.0238 (6)	0.0174 (5)	0.0006 (5)	0.0070 (4)	−0.0015 (5)
C2	0.0211 (6)	0.0209 (6)	0.0218 (6)	−0.0024 (5)	0.0068 (5)	−0.0005 (5)
C3	0.0212 (6)	0.0177 (6)	0.0217 (6)	0.0011 (5)	0.0056 (5)	−0.0026 (5)
C4	0.0177 (5)	0.0226 (6)	0.0179 (5)	0.0023 (5)	0.0056 (4)	−0.0013 (5)
C5	0.0195 (6)	0.0191 (6)	0.0208 (6)	0.0012 (5)	0.0080 (4)	0.0012 (4)
C6	0.0191 (5)	0.0186 (6)	0.0196 (6)	0.0017 (4)	0.0055 (4)	−0.0011 (4)
O3	0.0199 (4)	0.0241 (5)	0.0212 (4)	−0.0008 (3)	0.0085 (3)	−0.0053 (3)

Geometric parameters (Å, º)

N1—C13	1.3402 (17)	C19—C20	1.3838 (18)
N1—C14	1.3358 (19)	C20—H20	0.9300
N2—C18	1.3413 (16)	C21—C22	1.3916 (16)
N2—C19	1.3396 (16)	C21—C25	1.3979 (17)
N3—C23	1.3368 (17)	C22—H22	0.9300
N3—C24	1.3412 (16)	C22—C23	1.3852 (17)
N4—C28	1.3410 (17)	C23—H23	0.9300
N4—C29	1.3420 (17)	C24—H24	0.9300
C7—H7	0.9800	C24—C25	1.3877 (16)
C7—C8	1.5598 (15)	C25—H25	0.9300
C7—C10	1.5544 (15)	C26—C27	1.3921 (16)
C7—C11	1.4989 (15)	C26—C30	1.3917 (16)
C8—H8	0.9800	C27—H27	0.9300
C8—C9	1.5481 (15)	C27—C28	1.3890 (18)
C8—C16	1.5012 (16)	C28—H28	0.9300
C9—H9	0.9800	C29—H29	0.9300
C9—C10	1.5679 (15)	C29—C30	1.3849 (18)
C9—C21	1.5030 (15)	C30—H30	0.9300
C10—H10	0.9800	Cl1—C1	1.7401 (12)
C10—C26	1.5022 (16)	Cl2—C3	1.7395 (13)
C11—C12	1.3947 (17)	O1—H1	0.8200
C11—C15	1.3916 (17)	O1—C6	1.3487 (15)
C12—H12	0.9300	O2—H2	0.8200
C12—C13	1.3856 (17)	O2—C4	1.3473 (14)
C13—H13	0.9300	C1—C2	1.3843 (18)
C14—H14	0.9300	C1—C6	1.3982 (17)
C14—C15	1.3864 (18)	C2—H2A	0.9300
C15—H15	0.9300	C2—C3	1.3827 (17)
C16—C17	1.3920 (16)	C3—C4	1.3978 (18)
C16—C20	1.3936 (16)	C4—C5	1.3881 (18)
C17—H17	0.9300	C5—H5	0.9300
C17—C18	1.3868 (17)	C5—C6	1.3961 (16)
C18—H18	0.9300	O3—H3A	0.8499
C19—H19	0.9300	O3—H3B	0.8504
C14—N1—C13	116.88 (11)	C16—C20—H20	120.4
C19—N2—C18	116.85 (11)	C19—C20—C16	119.13 (11)
C23—N3—C24	116.74 (10)	C19—C20—H20	120.4
C28—N4—C29	115.73 (11)	C22—C21—C9	120.73 (11)
C8—C7—H7	109.3	C22—C21—C25	117.18 (11)
C10—C7—H7	109.3	C25—C21—C9	121.96 (10)
C10—C7—C8	87.12 (8)	C21—C22—H22	120.2
C11—C7—H7	109.3	C23—C22—C21	119.50 (11)
C11—C7—C8	118.24 (10)	C23—C22—H22	120.2
C11—C7—C10	121.59 (10)	N3—C23—C22	123.71 (11)
C7—C8—H8	108.6	N3—C23—H23	118.1
C9—C8—C7	88.29 (8)	C22—C23—H23	118.1
C9—C8—H8	108.6	N3—C24—H24	118.2
C16—C8—C7	120.20 (9)	N3—C24—C25	123.69 (11)
C16—C8—H8	108.6	C25—C24—H24	118.2
C16—C8—C9	120.67 (9)	C21—C25—H25	120.4
C8—C9—H9	109.2	C24—C25—C21	119.13 (11)
C8—C9—C10	87.06 (8)	C24—C25—H25	120.4
C10—C9—H9	109.2	C27—C26—C10	122.42 (11)
C21—C9—C8	117.67 (10)	C30—C26—C10	120.52 (11)
C21—C9—H9	109.2	C30—C26—C27	117.06 (11)
C21—C9—C10	122.42 (9)	C26—C27—H27	120.3
C7—C10—C9	87.77 (8)	C28—C27—C26	119.31 (11)
C7—C10—H10	110.0	C28—C27—H27	120.3
C9—C10—H10	110.0	N4—C28—C27	124.20 (12)
C26—C10—C7	119.43 (10)	N4—C28—H28	117.9
C26—C10—C9	117.68 (9)	C27—C28—H28	117.9
C26—C10—H10	110.0	N4—C29—H29	117.9
C12—C11—C7	121.88 (10)	N4—C29—C30	124.30 (12)
C15—C11—C7	120.83 (11)	C30—C29—H29	117.9
C15—C11—C12	117.14 (11)	C26—C30—H30	120.3
C11—C12—H12	120.4	C29—C30—C26	119.40 (11)
C13—C12—C11	119.11 (11)	C29—C30—H30	120.3
C13—C12—H12	120.4	C6—O1—H1	109.5
N1—C13—C12	123.76 (13)	C4—O2—H2	109.5
N1—C13—H13	118.1	C2—C1—Cl1	118.37 (9)
C12—C13—H13	118.1	C2—C1—C6	121.00 (11)
N1—C14—H14	118.3	C6—C1—Cl1	120.63 (10)
N1—C14—C15	123.34 (12)	C1—C2—H2A	120.0
C15—C14—H14	118.3	C3—C2—C1	119.91 (12)
C11—C15—H15	120.2	C3—C2—H2A	120.0
C14—C15—C11	119.66 (12)	C2—C3—Cl2	119.66 (10)
C14—C15—H15	120.2	C2—C3—C4	120.80 (12)
C17—C16—C8	122.30 (10)	C4—C3—Cl2	119.53 (9)
C17—C16—C20	117.38 (11)	O2—C4—C3	118.27 (11)
C20—C16—C8	120.24 (10)	O2—C4—C5	123.45 (11)
C16—C17—H17	120.3	C5—C4—C3	118.26 (11)
C18—C17—C16	119.50 (11)	C4—C5—H5	118.9
C18—C17—H17	120.3	C4—C5—C6	122.16 (11)
N2—C18—C17	123.29 (11)	C6—C5—H5	118.9
N2—C18—H18	118.4	O1—C6—C1	125.53 (11)
C17—C18—H18	118.4	O1—C6—C5	116.64 (11)
N2—C19—H19	118.1	C5—C6—C1	117.84 (11)
N2—C19—C20	123.83 (11)	H3A—O3—H3B	104.5
C20—C19—H19	118.1
N1—C14—C15—C11	0.5 (2)	C11—C12—C13—N1	0.17 (19)
N2—C19—C20—C16	−0.02 (19)	C12—C11—C15—C14	−2.95 (18)
N3—C24—C25—C21	0.36 (19)	C13—N1—C14—C15	2.23 (19)
N4—C29—C30—C26	0.2 (2)	C14—N1—C13—C12	−2.60 (19)
C7—C8—C9—C10	23.26 (8)	C15—C11—C12—C13	2.61 (17)
C7—C8—C9—C21	148.66 (10)	C16—C8—C9—C10	147.83 (10)
C7—C8—C16—C17	122.19 (12)	C16—C8—C9—C21	−86.77 (13)
C7—C8—C16—C20	−61.13 (15)	C16—C17—C18—N2	0.4 (2)
C7—C10—C26—C27	10.49 (16)	C17—C16—C20—C19	1.46 (17)
C7—C10—C26—C30	−169.79 (10)	C18—N2—C19—C20	−1.23 (19)
C7—C11—C12—C13	−173.02 (11)	C19—N2—C18—C17	1.02 (19)
C7—C11—C15—C14	172.73 (11)	C20—C16—C17—C18	−1.65 (18)
C8—C7—C10—C9	23.17 (8)	C21—C9—C10—C7	−144.57 (11)
C8—C7—C10—C26	143.96 (10)	C21—C9—C10—C26	93.09 (13)
C8—C7—C11—C12	53.04 (15)	C21—C22—C23—N3	0.04 (19)
C8—C7—C11—C15	−122.43 (12)	C22—C21—C25—C24	−1.88 (17)
C8—C9—C10—C7	−23.36 (8)	C23—N3—C24—C25	1.37 (18)
C8—C9—C10—C26	−145.69 (10)	C24—N3—C23—C22	−1.58 (18)
C8—C9—C21—C22	129.18 (11)	C25—C21—C22—C23	1.71 (17)
C8—C9—C21—C25	−46.63 (15)	C26—C27—C28—N4	0.32 (19)
C8—C16—C17—C18	175.12 (11)	C27—C26—C30—C29	−0.36 (17)
C8—C16—C20—C19	−175.38 (11)	C28—N4—C29—C30	0.28 (19)
C9—C8—C16—C17	14.44 (17)	C29—N4—C28—C27	−0.52 (19)
C9—C8—C16—C20	−168.89 (11)	C30—C26—C27—C28	0.14 (17)
C9—C10—C26—C27	114.71 (12)	Cl1—C1—C2—C3	−178.57 (9)
C9—C10—C26—C30	−65.58 (14)	Cl1—C1—C6—O1	−1.12 (18)
C9—C21—C22—C23	−174.30 (11)	Cl1—C1—C6—C5	179.05 (9)
C9—C21—C25—C24	174.07 (11)	Cl2—C3—C4—O2	−0.90 (16)
C10—C7—C8—C9	−23.48 (8)	Cl2—C3—C4—C5	177.76 (9)
C10—C7—C8—C16	−148.44 (10)	O2—C4—C5—C6	−179.51 (11)
C10—C7—C11—C12	−52.23 (16)	C1—C2—C3—Cl2	−179.30 (9)
C10—C7—C11—C15	132.30 (12)	C1—C2—C3—C4	−0.15 (19)
C10—C9—C21—C22	−125.49 (12)	C2—C1—C6—O1	179.05 (12)
C10—C9—C21—C25	58.70 (16)	C2—C1—C6—C5	−0.78 (18)
C10—C26—C27—C28	179.86 (11)	C2—C3—C4—O2	179.95 (11)
C10—C26—C30—C29	179.92 (11)	C2—C3—C4—C5	−1.39 (18)
C11—C7—C8—C9	−148.12 (10)	C3—C4—C5—C6	1.90 (18)
C11—C7—C8—C16	86.92 (13)	C4—C5—C6—O1	179.32 (11)
C11—C7—C10—C9	144.85 (11)	C4—C5—C6—C1	−0.83 (18)
C11—C7—C10—C26	−94.36 (13)	C6—C1—C2—C3	1.26 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N4^i	0.98	2.67	3.6375 (16)	169
O1—H1···N1	0.82	1.98	2.7296 (14)	151
O1—H1···Cl1	0.82	2.62	3.0945 (10)	119
O2—H2···O3	0.82	1.78	2.5952 (13)	175
O3—H3A···N2^ii	0.85	1.91	2.7617 (14)	177
O3—H3B···N3^iii	0.85	1.96	2.8036 (13)	170

Symmetry codes: (i) x, y+1, z; (ii) x−1, y, z; (iii) x−1, −y+3/2, z+1/2.