Does the size of a crystal matter in an X-ray crystal structure analysis of a small molecule?

The crystal structures of C₇H₈FN₃, C₂₀H₂₅Br, [Cu(H₂O)₂(C₆H₁₂N₄)(C₇H₃N₂O₆)₂]·2H₂O, [SnCl(H₂O)(C₆H₅)₃(C₁₀H₈N₂)]₂ and [Pb(NO₃)₂(C₃H₉N₃S)] refined on numerically absorption-corrected reflections to low R values although the dimensions of the crystals exceeded the diameter of the X-ray beam collimator. The R values for the organic and copper compounds were not significantly different when smaller specimens cut from the large crystals were used. For the tin complex, a large peak persisted in the difference map for all sizes, and for the lead complex, the difference Fourier map was more diffuse the smaller the specimen.

Computing details

For all compounds, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

(S1) 3-Amino-1-(4-fluorophenyl)thiourea

Crystal data

C7H8FN3S	F(000) = 384
Mr = 185.22	Dx = 1.501 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2257 reflections
a = 11.9470 (8) Å	θ = 4.0–27.5°
b = 5.5093 (3) Å	µ = 0.36 mm^−1
c = 12.4564 (7) Å	T = 100 K
β = 91.712 (6)°	Prism, colorless
V = 819.51 (8) Å^3	0.71 × 0.36 × 0.18 mm
Z = 4

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	1892 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1536 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.035
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 3.3°
ω scan	h = −14→15
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −5→7
Tmin = 0.846, Tmax = 0.942	l = −16→16
6015 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0336P)^2 + 0.4252P] where P = (Fo^2 + 2Fc^2)/3
1892 reflections	(Δ/σ)max = 0.001
125 parameters	Δρmax = 0.29 e Å^−3
4 restraints	Δρmin = −0.26 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.09528 (4)	0.49192 (8)	0.35353 (3)	0.02152 (15)
F1	0.46547 (9)	0.75462 (18)	0.01946 (8)	0.0222 (3)
C1	0.14599 (14)	0.7342 (3)	0.42360 (13)	0.0144 (3)
C2	0.28858 (14)	0.8397 (3)	0.29390 (13)	0.0141 (3)
C3	0.27938 (15)	1.0122 (3)	0.21279 (14)	0.0166 (4)
H3A	0.2321	1.1491	0.2211	0.020*
C4	0.33912 (15)	0.9851 (3)	0.11937 (14)	0.0173 (4)
H4	0.3337	1.1024	0.0636	0.021*
C5	0.40626 (15)	0.7836 (3)	0.11000 (13)	0.0160 (4)
C6	0.41738 (14)	0.6088 (3)	0.18914 (13)	0.0159 (4)
H6	0.4645	0.4718	0.1801	0.019*
C7	0.35772 (14)	0.6388 (3)	0.28234 (13)	0.0155 (4)
H7	0.3642	0.5219	0.3382	0.019*
N1	0.14450 (13)	0.9982 (3)	0.57559 (12)	0.0170 (3)
N2	0.09965 (12)	0.8002 (3)	0.51568 (11)	0.0163 (3)
N3	0.23008 (12)	0.8746 (3)	0.39037 (11)	0.0159 (3)
H11	0.0911 (13)	1.108 (3)	0.5792 (15)	0.018 (5)*
H12	0.1641 (18)	0.946 (4)	0.6405 (10)	0.031 (6)*
H2	0.0489 (13)	0.709 (3)	0.5452 (15)	0.022 (5)*
H3	0.2440 (19)	1.008 (3)	0.4267 (15)	0.030 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0254 (3)	0.0221 (3)	0.0176 (2)	−0.00999 (18)	0.01017 (18)	−0.00590 (18)
F1	0.0272 (6)	0.0235 (6)	0.0165 (5)	−0.0002 (4)	0.0115 (4)	−0.0016 (4)
C1	0.0139 (9)	0.0160 (8)	0.0134 (8)	0.0016 (6)	0.0019 (6)	0.0014 (6)
C2	0.0121 (8)	0.0155 (8)	0.0147 (8)	−0.0036 (6)	0.0025 (6)	−0.0020 (6)
C3	0.0161 (9)	0.0137 (8)	0.0199 (8)	−0.0003 (6)	0.0023 (7)	−0.0010 (7)
C4	0.0202 (9)	0.0154 (8)	0.0166 (8)	−0.0019 (7)	0.0030 (7)	0.0032 (7)
C5	0.0169 (9)	0.0186 (9)	0.0126 (8)	−0.0044 (7)	0.0053 (6)	−0.0036 (7)
C6	0.0140 (9)	0.0147 (8)	0.0190 (8)	0.0011 (6)	0.0015 (7)	−0.0017 (7)
C7	0.0156 (9)	0.0161 (8)	0.0149 (8)	−0.0029 (6)	0.0010 (7)	0.0023 (7)
N1	0.0188 (8)	0.0179 (8)	0.0143 (7)	0.0014 (6)	−0.0001 (6)	−0.0036 (6)
N2	0.0168 (8)	0.0182 (8)	0.0143 (7)	−0.0041 (6)	0.0048 (6)	−0.0019 (6)
N3	0.0171 (8)	0.0154 (7)	0.0156 (7)	−0.0037 (6)	0.0061 (6)	−0.0038 (6)

Geometric parameters (Å, º)

S1—C1	1.6967 (17)	C4—H4	0.9500
F1—C5	1.3586 (19)	C5—C6	1.382 (2)
C1—N2	1.339 (2)	C6—C7	1.390 (2)
C1—N3	1.343 (2)	C6—H6	0.9500
C2—C7	1.391 (2)	C7—H7	0.9500
C2—C3	1.389 (2)	N1—N2	1.4179 (19)
C2—N3	1.421 (2)	N1—H11	0.882 (9)
C3—C4	1.391 (2)	N1—H12	0.883 (9)
C3—H3A	0.9500	N2—H2	0.875 (9)
C4—C5	1.376 (2)	N3—H3	0.875 (9)
N2—C1—N3	116.10 (15)	C5—C6—C7	118.16 (16)
N2—C1—S1	120.26 (13)	C5—C6—H6	120.9
N3—C1—S1	123.60 (13)	C7—C6—H6	120.9
C7—C2—C3	120.21 (16)	C2—C7—C6	120.14 (15)
C7—C2—N3	120.27 (15)	C2—C7—H7	119.9
C3—C2—N3	119.48 (15)	C6—C7—H7	119.9
C2—C3—C4	120.24 (16)	N2—N1—H11	107.1 (13)
C2—C3—H3A	119.9	N2—N1—H12	108.5 (14)
C4—C3—H3A	119.9	H11—N1—H12	110.5 (18)
C5—C4—C3	118.17 (16)	C1—N2—N1	120.03 (14)
C5—C4—H4	120.9	C1—N2—H2	120.9 (13)
C3—C4—H4	120.9	N1—N2—H2	118.3 (13)
F1—C5—C4	118.96 (15)	C1—N3—C2	125.01 (14)
F1—C5—C6	117.97 (15)	C1—N3—H3	117.1 (15)
C4—C5—C6	123.06 (16)	C2—N3—H3	117.4 (15)
C7—C2—C3—C4	0.1 (2)	N3—C2—C7—C6	−178.12 (15)
N3—C2—C3—C4	177.77 (15)	C5—C6—C7—C2	0.4 (2)
C2—C3—C4—C5	0.3 (3)	N3—C1—N2—N1	−4.1 (2)
C3—C4—C5—F1	−179.79 (15)	S1—C1—N2—N1	178.07 (12)
C3—C4—C5—C6	−0.4 (3)	N2—C1—N3—C2	−178.47 (15)
F1—C5—C6—C7	179.43 (14)	S1—C1—N3—C2	−0.7 (2)
C4—C5—C6—C7	0.0 (3)	C7—C2—N3—C1	−68.1 (2)
C3—C2—C7—C6	−0.5 (2)	C3—C2—N3—C1	114.20 (18)

(S2) 3-Amino-1-(4-fluorophenyl)thiourea

Crystal data

C7H8FN3S	F(000) = 384
Mr = 185.22	Dx = 1.500 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2228 reflections
a = 11.9525 (8) Å	θ = 3.4–27.5°
b = 5.5111 (3) Å	µ = 0.36 mm^−1
c = 12.4566 (7) Å	T = 100 K
β = 91.699 (5)°	Prism, colorless
V = 820.17 (8) Å^3	0.47 × 0.40 × 0.17 mm
Z = 4

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	1892 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1513 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.037
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 3.3°
ω scan	h = −15→11
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −7→6
Tmin = 0.874, Tmax = 0.945	l = −16→16
5976 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0383P)^2 + 0.3747P] where P = (Fo^2 + 2Fc^2)/3
1892 reflections	(Δ/σ)max = 0.001
125 parameters	Δρmax = 0.28 e Å^−3
4 restraints	Δρmin = −0.24 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.09528 (4)	0.49205 (8)	0.35351 (4)	0.02167 (15)
F1	0.46546 (9)	0.75468 (18)	0.01943 (8)	0.0227 (3)
C1	0.14591 (14)	0.7341 (3)	0.42356 (13)	0.0147 (4)
C2	0.28873 (14)	0.8395 (3)	0.29360 (13)	0.0142 (4)
C3	0.27940 (15)	1.0116 (3)	0.21280 (14)	0.0163 (4)
H3A	0.2319	1.1481	0.2213	0.020*
C4	0.33914 (15)	0.9858 (3)	0.11925 (14)	0.0177 (4)
H4	0.3338	1.1034	0.0636	0.021*
C5	0.40647 (14)	0.7835 (3)	0.11006 (14)	0.0159 (4)
C6	0.41726 (14)	0.6088 (3)	0.18900 (14)	0.0156 (4)
H6	0.4641	0.4716	0.1798	0.019*
C7	0.35786 (14)	0.6384 (3)	0.28235 (14)	0.0160 (4)
H7	0.3644	0.5218	0.3383	0.019*
N1	0.14450 (13)	0.9985 (3)	0.57555 (12)	0.0167 (3)
N2	0.09980 (12)	0.7999 (3)	0.51568 (11)	0.0164 (3)
N3	0.23016 (12)	0.8744 (3)	0.39025 (12)	0.0164 (3)
H11	0.0910 (13)	1.108 (3)	0.5818 (16)	0.023 (5)*
H12	0.1632 (18)	0.947 (4)	0.6410 (10)	0.029 (6)*
H2	0.0495 (15)	0.709 (3)	0.5466 (17)	0.034 (6)*
H3	0.2421 (19)	1.006 (3)	0.4278 (15)	0.031 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0259 (3)	0.0222 (3)	0.0174 (2)	−0.01006 (19)	0.00937 (18)	−0.00597 (19)
F1	0.0279 (6)	0.0229 (6)	0.0180 (5)	−0.0001 (5)	0.0110 (4)	−0.0013 (5)
C1	0.0141 (8)	0.0158 (8)	0.0141 (8)	0.0026 (7)	0.0002 (6)	0.0009 (7)
C2	0.0124 (8)	0.0167 (8)	0.0137 (8)	−0.0042 (7)	0.0018 (6)	−0.0028 (7)
C3	0.0152 (9)	0.0142 (8)	0.0197 (9)	0.0001 (7)	0.0014 (7)	0.0003 (7)
C4	0.0204 (9)	0.0171 (9)	0.0157 (9)	−0.0014 (7)	0.0020 (7)	0.0027 (7)
C5	0.0151 (9)	0.0205 (9)	0.0123 (8)	−0.0040 (7)	0.0033 (6)	−0.0036 (7)
C6	0.0135 (8)	0.0145 (8)	0.0187 (8)	0.0009 (7)	−0.0002 (7)	−0.0028 (7)
C7	0.0164 (9)	0.0151 (8)	0.0163 (8)	−0.0017 (7)	−0.0004 (7)	0.0005 (7)
N1	0.0188 (8)	0.0179 (8)	0.0132 (8)	0.0016 (6)	−0.0006 (6)	−0.0041 (7)
N2	0.0170 (8)	0.0185 (8)	0.0139 (7)	−0.0035 (6)	0.0031 (6)	−0.0015 (6)
N3	0.0181 (8)	0.0150 (7)	0.0162 (7)	−0.0039 (6)	0.0047 (6)	−0.0035 (6)

Geometric parameters (Å, º)

S1—C1	1.6958 (18)	C4—H4	0.9500
F1—C5	1.3579 (18)	C5—C6	1.379 (2)
C1—N2	1.338 (2)	C6—C7	1.390 (2)
C1—N3	1.345 (2)	C6—H6	0.9500
C2—C3	1.385 (2)	C7—H7	0.9500
C2—C7	1.392 (2)	N1—N2	1.420 (2)
C2—N3	1.424 (2)	N1—H11	0.883 (9)
C3—C4	1.392 (2)	N1—H12	0.886 (9)
C3—H3A	0.9500	N2—H2	0.878 (9)
C4—C5	1.382 (2)	N3—H3	0.873 (9)
N2—C1—N3	116.11 (15)	C5—C6—C7	118.37 (16)
N2—C1—S1	120.32 (13)	C5—C6—H6	120.8
N3—C1—S1	123.54 (13)	C7—C6—H6	120.8
C3—C2—C7	120.48 (15)	C6—C7—C2	119.82 (16)
C3—C2—N3	119.41 (15)	C6—C7—H7	120.1
C7—C2—N3	120.07 (15)	C2—C7—H7	120.1
C2—C3—C4	120.41 (16)	N2—N1—H11	108.0 (14)
C2—C3—H3A	119.8	N2—N1—H12	108.5 (14)
C4—C3—H3A	119.8	H11—N1—H12	107.5 (19)
C5—C4—C3	117.80 (16)	C1—N2—N1	120.09 (14)
C5—C4—H4	121.1	C1—N2—H2	121.8 (14)
C3—C4—H4	121.1	N1—N2—H2	117.3 (14)
F1—C5—C6	118.10 (15)	C1—N3—C2	125.08 (15)
F1—C5—C4	118.78 (15)	C1—N3—H3	115.1 (15)
C6—C5—C4	123.12 (16)	C2—N3—H3	119.3 (15)
C7—C2—C3—C4	0.0 (3)	C3—C2—C7—C6	−0.6 (3)
N3—C2—C3—C4	177.62 (15)	N3—C2—C7—C6	−178.21 (15)
C2—C3—C4—C5	0.5 (3)	N3—C1—N2—N1	−3.8 (2)
C3—C4—C5—F1	179.97 (15)	S1—C1—N2—N1	178.22 (12)
C3—C4—C5—C6	−0.3 (3)	N2—C1—N3—C2	−178.54 (16)
F1—C5—C6—C7	179.44 (15)	S1—C1—N3—C2	−0.6 (2)
C4—C5—C6—C7	−0.3 (3)	C3—C2—N3—C1	114.07 (19)
C5—C6—C7—C2	0.7 (2)	C7—C2—N3—C1	−68.3 (2)

(S3) 3-Amino-1-(4-fluorophenyl)thiourea

Crystal data

C7H8FN3S	F(000) = 384
Mr = 185.22	Dx = 1.507 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2330 reflections
a = 11.9359 (7) Å	θ = 3.6–27.5°
b = 5.5005 (3) Å	µ = 0.36 mm^−1
c = 12.4375 (7) Å	T = 100 K
β = 91.776 (5)°	Prism, colorless
V = 816.17 (8) Å^3	0.33 × 0.28 × 0.17 mm
Z = 4

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	1881 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1475 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.041
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.5°, θmin = 3.7°
ω scan	h = −15→12
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −7→7
Tmin = 0.910, Tmax = 0.945	l = −16→11
6384 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0424P)^2 + 0.3065P] where P = (Fo^2 + 2Fc^2)/3
1881 reflections	(Δ/σ)max = 0.001
125 parameters	Δρmax = 0.32 e Å^−3
4 restraints	Δρmin = −0.27 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.09539 (4)	0.49192 (9)	0.35355 (4)	0.02110 (16)
F1	0.46549 (9)	0.75452 (19)	0.01941 (8)	0.0215 (3)
C1	0.14601 (14)	0.7341 (3)	0.42378 (14)	0.0135 (4)
C2	0.28890 (14)	0.8393 (3)	0.29363 (13)	0.0137 (4)
C3	0.27961 (15)	1.0115 (3)	0.21276 (15)	0.0161 (4)
H3A	0.2321	1.1483	0.2212	0.019*
C4	0.33928 (15)	0.9858 (3)	0.11944 (14)	0.0164 (4)
H4	0.3341	1.1039	0.0638	0.020*
C5	0.40620 (14)	0.7837 (3)	0.11014 (14)	0.0143 (4)
C6	0.41718 (14)	0.6091 (3)	0.18898 (14)	0.0149 (4)
H6	0.4642	0.4718	0.1798	0.018*
C7	0.35781 (14)	0.6384 (3)	0.28227 (14)	0.0147 (4)
H7	0.3643	0.5212	0.3382	0.018*
N1	0.14459 (13)	0.9984 (3)	0.57568 (12)	0.0162 (3)
N2	0.09988 (12)	0.7999 (3)	0.51589 (12)	0.0161 (3)
N3	0.23006 (12)	0.8745 (3)	0.39019 (12)	0.0152 (3)
H11	0.0911 (14)	1.109 (3)	0.5819 (17)	0.028 (6)*
H12	0.1632 (17)	0.948 (3)	0.6407 (10)	0.020 (5)*
H2	0.0505 (15)	0.707 (3)	0.5464 (16)	0.027 (6)*
H3	0.2433 (17)	1.007 (3)	0.4270 (15)	0.022 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0250 (3)	0.0214 (3)	0.0174 (3)	−0.00988 (18)	0.00947 (19)	−0.00599 (19)
F1	0.0258 (6)	0.0226 (6)	0.0168 (6)	0.0004 (4)	0.0106 (4)	−0.0012 (4)
C1	0.0131 (9)	0.0148 (9)	0.0126 (9)	0.0018 (6)	−0.0007 (6)	0.0003 (7)
C2	0.0125 (8)	0.0159 (9)	0.0128 (9)	−0.0026 (7)	0.0025 (6)	−0.0023 (7)
C3	0.0154 (9)	0.0135 (9)	0.0195 (9)	0.0009 (7)	0.0013 (7)	−0.0005 (7)
C4	0.0192 (9)	0.0147 (9)	0.0153 (9)	−0.0023 (7)	0.0016 (7)	0.0026 (7)
C5	0.0123 (9)	0.0180 (9)	0.0129 (9)	−0.0041 (7)	0.0041 (6)	−0.0038 (7)
C6	0.0118 (9)	0.0130 (9)	0.0200 (9)	0.0008 (6)	0.0004 (7)	−0.0023 (7)
C7	0.0148 (9)	0.0140 (9)	0.0153 (9)	−0.0024 (7)	−0.0002 (7)	0.0005 (7)
N1	0.0175 (8)	0.0174 (8)	0.0135 (8)	0.0012 (6)	−0.0010 (6)	−0.0040 (6)
N2	0.0162 (8)	0.0180 (8)	0.0143 (8)	−0.0033 (6)	0.0033 (6)	−0.0009 (6)
N3	0.0167 (8)	0.0137 (8)	0.0154 (8)	−0.0039 (6)	0.0046 (6)	−0.0033 (6)

Geometric parameters (Å, º)

S1—C1	1.6942 (18)	C4—H4	0.9500
F1—C5	1.3600 (19)	C5—C6	1.376 (2)
C1—N2	1.336 (2)	C6—C7	1.388 (2)
C1—N3	1.343 (2)	C6—H6	0.9500
C2—C3	1.384 (2)	C7—H7	0.9500
C2—C7	1.387 (2)	N1—N2	1.416 (2)
C2—N3	1.423 (2)	N1—H11	0.885 (9)
C3—C4	1.388 (3)	N1—H12	0.879 (9)
C3—H3A	0.9500	N2—H2	0.874 (9)
C4—C5	1.376 (2)	N3—H3	0.870 (9)
N2—C1—N3	116.29 (15)	C5—C6—C7	118.35 (16)
N2—C1—S1	120.33 (13)	C5—C6—H6	120.8
N3—C1—S1	123.35 (13)	C7—C6—H6	120.8
C3—C2—C7	120.39 (16)	C2—C7—C6	119.82 (16)
C3—C2—N3	119.31 (16)	C2—C7—H7	120.1
C7—C2—N3	120.26 (16)	C6—C7—H7	120.1
C2—C3—C4	120.42 (16)	N2—N1—H11	108.3 (15)
C2—C3—H3A	119.8	N2—N1—H12	108.6 (14)
C4—C3—H3A	119.8	H11—N1—H12	107.5 (19)
C5—C4—C3	117.86 (17)	C1—N2—N1	120.01 (14)
C5—C4—H4	121.1	C1—N2—H2	121.0 (14)
C3—C4—H4	121.1	N1—N2—H2	118.0 (14)
F1—C5—C4	118.93 (16)	C1—N3—C2	125.26 (15)
F1—C5—C6	117.91 (15)	C1—N3—H3	116.2 (14)
C4—C5—C6	123.15 (16)	C2—N3—H3	118.1 (14)
C7—C2—C3—C4	−0.1 (3)	N3—C2—C7—C6	−178.26 (15)
N3—C2—C3—C4	177.69 (16)	C5—C6—C7—C2	0.5 (3)
C2—C3—C4—C5	0.7 (3)	N3—C1—N2—N1	−3.9 (2)
C3—C4—C5—F1	180.00 (15)	S1—C1—N2—N1	178.26 (12)
C3—C4—C5—C6	−0.6 (3)	N2—C1—N3—C2	−178.75 (16)
F1—C5—C6—C7	179.43 (15)	S1—C1—N3—C2	−1.0 (2)
C4—C5—C6—C7	0.0 (3)	C3—C2—N3—C1	114.3 (2)
C3—C2—C7—C6	−0.4 (3)	C7—C2—N3—C1	−67.8 (2)

(S4) 3-Amino-1-(4-fluorophenyl)thiourea

Crystal data

C7H8FN3S	F(000) = 384
Mr = 185.22	Dx = 1.499 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2061 reflections
a = 11.9533 (8) Å	θ = 3.7–27.5°
b = 5.5087 (4) Å	µ = 0.36 mm^−1
c = 12.4688 (8) Å	T = 100 K
β = 91.699 (6)°	Prism, colorless
V = 820.67 (10) Å^3	0.30 × 0.25 × 0.14 mm
Z = 4

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	1894 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1475 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.041
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 3.3°
ω scan	h = −11→15
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −7→7
Tmin = 0.915, Tmax = 0.952	l = −14→16
5875 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0367P)^2 + 0.3187P] where P = (Fo^2 + 2Fc^2)/3
1894 reflections	(Δ/σ)max = 0.001
125 parameters	Δρmax = 0.26 e Å^−3
4 restraints	Δρmin = −0.26 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.09534 (4)	0.49188 (9)	0.35351 (4)	0.02143 (16)
F1	0.46545 (9)	0.75466 (19)	0.01932 (8)	0.0221 (3)
C1	0.14569 (14)	0.7340 (3)	0.42348 (14)	0.0134 (4)
C2	0.28879 (14)	0.8395 (3)	0.29358 (13)	0.0138 (4)
C3	0.27957 (15)	1.0112 (3)	0.21299 (15)	0.0161 (4)
H3A	0.2322	1.1479	0.2216	0.019*
C4	0.33900 (15)	0.9860 (3)	0.11930 (14)	0.0170 (4)
H4	0.3335	1.1035	0.0636	0.020*
C5	0.40620 (15)	0.7837 (3)	0.11038 (14)	0.0154 (4)
C6	0.41732 (14)	0.6086 (3)	0.18892 (14)	0.0154 (4)
H6	0.4641	0.4714	0.1795	0.018*
C7	0.35797 (14)	0.6386 (3)	0.28240 (14)	0.0150 (4)
H7	0.3647	0.5221	0.3384	0.018*
N1	0.14463 (13)	0.9983 (3)	0.57561 (12)	0.0165 (3)
N2	0.09959 (13)	0.8002 (3)	0.51576 (12)	0.0160 (3)
N3	0.23012 (13)	0.8744 (3)	0.39055 (12)	0.0164 (3)
H11	0.0911 (13)	1.106 (3)	0.5818 (15)	0.022 (6)*
H12	0.1629 (18)	0.943 (4)	0.6406 (10)	0.033 (6)*
H2	0.0494 (15)	0.708 (3)	0.5453 (16)	0.032 (6)*
H3	0.2423 (19)	1.007 (3)	0.4287 (16)	0.034 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0250 (3)	0.0214 (3)	0.0184 (3)	−0.0101 (2)	0.01017 (19)	−0.0060 (2)
F1	0.0267 (6)	0.0226 (6)	0.0177 (6)	0.0006 (5)	0.0115 (5)	−0.0011 (5)
C1	0.0128 (9)	0.0154 (9)	0.0122 (8)	0.0012 (7)	0.0005 (6)	0.0017 (7)
C2	0.0123 (9)	0.0145 (9)	0.0147 (9)	−0.0034 (7)	0.0027 (7)	−0.0034 (7)
C3	0.0146 (9)	0.0121 (9)	0.0218 (9)	0.0003 (7)	0.0028 (7)	−0.0022 (8)
C4	0.0204 (10)	0.0154 (9)	0.0153 (9)	−0.0011 (7)	0.0017 (7)	0.0038 (8)
C5	0.0136 (9)	0.0203 (10)	0.0126 (8)	−0.0043 (7)	0.0046 (7)	−0.0037 (7)
C6	0.0112 (9)	0.0149 (9)	0.0202 (9)	−0.0002 (7)	0.0013 (7)	−0.0022 (8)
C7	0.0157 (9)	0.0140 (9)	0.0153 (9)	−0.0024 (7)	−0.0005 (7)	0.0027 (8)
N1	0.0181 (8)	0.0172 (8)	0.0142 (8)	0.0014 (6)	0.0002 (6)	−0.0032 (7)
N2	0.0153 (8)	0.0180 (8)	0.0148 (8)	−0.0035 (6)	0.0034 (6)	−0.0027 (6)
N3	0.0176 (8)	0.0151 (8)	0.0167 (8)	−0.0040 (6)	0.0054 (6)	−0.0033 (7)

Geometric parameters (Å, º)

S1—C1	1.6943 (18)	C4—H4	0.9500
F1—C5	1.3654 (19)	C5—C6	1.378 (3)
C1—N2	1.341 (2)	C6—C7	1.392 (2)
C1—N3	1.345 (2)	C6—H6	0.9500
C2—C3	1.382 (2)	C7—H7	0.9500
C2—C7	1.391 (2)	N1—N2	1.419 (2)
C2—N3	1.429 (2)	N1—H11	0.879 (9)
C3—C4	1.392 (2)	N1—H12	0.888 (9)
C3—H3A	0.9500	N2—H2	0.876 (9)
C4—C5	1.380 (3)	N3—H3	0.880 (10)
N2—C1—N3	115.89 (16)	C5—C6—C7	118.11 (17)
N2—C1—S1	120.48 (13)	C5—C6—H6	120.9
N3—C1—S1	123.61 (13)	C7—C6—H6	120.9
C3—C2—C7	120.44 (16)	C2—C7—C6	119.83 (16)
C3—C2—N3	119.51 (16)	C2—C7—H7	120.1
C7—C2—N3	120.01 (16)	C6—C7—H7	120.1
C2—C3—C4	120.66 (17)	N2—N1—H11	107.6 (14)
C2—C3—H3A	119.7	N2—N1—H12	107.1 (15)
C4—C3—H3A	119.7	H11—N1—H12	108.3 (19)
C5—C4—C3	117.45 (17)	C1—N2—N1	120.08 (15)
C5—C4—H4	121.3	C1—N2—H2	120.4 (14)
C3—C4—H4	121.3	N1—N2—H2	118.7 (14)
F1—C5—C6	117.87 (16)	C1—N3—C2	124.93 (15)
F1—C5—C4	118.63 (16)	C1—N3—H3	115.1 (15)
C6—C5—C4	123.50 (16)	C2—N3—H3	119.5 (15)
C7—C2—C3—C4	0.2 (3)	N3—C2—C7—C6	−178.29 (16)
N3—C2—C3—C4	177.69 (16)	C5—C6—C7—C2	0.9 (3)
C2—C3—C4—C5	0.3 (3)	N3—C1—N2—N1	−3.8 (2)
C3—C4—C5—F1	−179.96 (15)	S1—C1—N2—N1	177.95 (13)
C3—C4—C5—C6	−0.2 (3)	N2—C1—N3—C2	−178.45 (16)
F1—C5—C6—C7	179.36 (15)	S1—C1—N3—C2	−0.3 (3)
C4—C5—C6—C7	−0.4 (3)	C3—C2—N3—C1	113.9 (2)
C3—C2—C7—C6	−0.8 (3)	C7—C2—N3—C1	−68.6 (2)

(Br1) (2-Bromo-1,2-diphenylethenyl)benzene

Crystal data

C20H15Br	F(000) = 680
Mr = 335.23	Dx = 1.479 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2747 reflections
a = 5.6130 (4) Å	θ = 3.5–27.5°
b = 8.5301 (5) Å	µ = 2.72 mm^−1
c = 31.4348 (17) Å	T = 100 K
V = 1505.08 (16) Å^3	Prism, colorless
Z = 4	0.85 × 0.36 × 0.22 mm

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	3488 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3007 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.044
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 3.1°
ω scan	h = −4→7
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −9→11
Tmin = 0.251, Tmax = 0.601	l = −34→40
6537 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.093	w = 1/[σ^2(Fo^2) + (0.0335P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
3488 reflections	Δρmax = 1.06 e Å^−3
190 parameters	Δρmin = −0.84 e Å^−3
0 restraints	Absolute structure: Flack parameter from 1430 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.014 (14)

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

	x	y	z	Uiso*/Ueq
Br1	1.00568 (9)	0.15217 (4)	0.208409 (9)	0.01851 (11)
C1	1.0531 (6)	0.0477 (4)	0.12290 (11)	0.0138 (8)
C2	1.2627 (7)	−0.0356 (5)	0.13109 (12)	0.0186 (9)
H2	1.3673	−0.0013	0.1529	0.022*
C3	1.3188 (7)	−0.1682 (5)	0.10751 (12)	0.0174 (9)
H3	1.4623	−0.2234	0.1131	0.021*
C4	1.1667 (8)	−0.2204 (5)	0.07581 (12)	0.0191 (9)
H4	1.2059	−0.3108	0.0596	0.023*
C5	0.9586 (7)	−0.1403 (4)	0.06796 (11)	0.0173 (9)
H5	0.8529	−0.1767	0.0465	0.021*
C6	0.9014 (7)	−0.0064 (4)	0.09112 (11)	0.0147 (8)
H6	0.7579	0.0484	0.0852	0.018*
C7	0.9107 (7)	0.3668 (4)	0.08773 (11)	0.0128 (8)
C8	1.1090 (7)	0.3331 (4)	0.06230 (12)	0.0149 (8)
H8	1.2386	0.2760	0.0740	0.018*
C9	1.1190 (7)	0.3820 (4)	0.02021 (12)	0.0153 (9)
H9	1.2537	0.3576	0.0032	0.018*
C10	0.9301 (7)	0.4671 (4)	0.00319 (11)	0.0146 (9)
H10	0.9362	0.5016	−0.0255	0.017*
C11	0.7335 (7)	0.5016 (4)	0.02798 (12)	0.0158 (9)
H11	0.6043	0.5588	0.0161	0.019*
C12	0.7242 (7)	0.4532 (4)	0.06984 (11)	0.0132 (8)
H12	0.5893	0.4790	0.0867	0.016*
C13	0.7788 (7)	0.4408 (4)	0.16237 (11)	0.0129 (8)
C14	0.8701 (7)	0.5918 (4)	0.16627 (11)	0.0150 (9)
H14	1.0138	0.6190	0.1521	0.018*
C15	0.7521 (8)	0.7030 (5)	0.19082 (12)	0.0223 (10)
H15	0.8162	0.8055	0.1936	0.027*
C16	0.5415 (7)	0.6646 (5)	0.21110 (11)	0.0202 (9)
H16	0.4607	0.7408	0.2278	0.024*
C17	0.4486 (7)	0.5150 (5)	0.20708 (11)	0.0222 (9)
H17	0.3029	0.4889	0.2207	0.027*
C18	0.5678 (7)	0.4033 (5)	0.18320 (12)	0.0185 (9)
H18	0.5048	0.3002	0.1810	0.022*
C19	0.9804 (8)	0.1856 (4)	0.14850 (10)	0.0158 (8)
C20	0.8966 (7)	0.3226 (4)	0.13411 (11)	0.0155 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0297 (2)	0.01639 (17)	0.00946 (16)	−0.0002 (2)	0.0014 (2)	0.00176 (13)
C1	0.011 (2)	0.0131 (16)	0.0170 (17)	−0.0026 (16)	0.0034 (14)	0.0008 (15)
C2	0.020 (2)	0.022 (2)	0.0137 (19)	−0.002 (2)	0.0019 (16)	0.0035 (18)
C3	0.016 (2)	0.016 (2)	0.020 (2)	0.0061 (19)	0.0051 (16)	0.0097 (18)
C4	0.026 (3)	0.0126 (19)	0.019 (2)	−0.0058 (19)	0.0064 (18)	−0.0025 (18)
C5	0.020 (3)	0.0145 (17)	0.0172 (17)	−0.004 (2)	−0.0022 (15)	−0.0008 (15)
C6	0.017 (2)	0.0118 (18)	0.0157 (18)	−0.0020 (16)	−0.0008 (15)	0.0071 (16)
C7	0.015 (2)	0.0101 (18)	0.0131 (17)	−0.0036 (16)	−0.0010 (14)	0.0011 (16)
C8	0.016 (2)	0.0090 (18)	0.020 (2)	−0.0003 (17)	0.0001 (15)	0.0021 (18)
C9	0.019 (2)	0.0115 (19)	0.0152 (19)	−0.0033 (17)	0.0049 (15)	−0.0062 (17)
C10	0.023 (2)	0.0124 (17)	0.0078 (16)	−0.0052 (17)	−0.0012 (14)	0.0015 (16)
C11	0.016 (2)	0.0106 (19)	0.021 (2)	0.0017 (17)	−0.0064 (17)	−0.0001 (16)
C12	0.012 (2)	0.0135 (18)	0.0141 (19)	−0.0011 (17)	0.0005 (15)	−0.0026 (16)
C13	0.016 (2)	0.0097 (17)	0.0128 (18)	0.0020 (17)	0.0028 (15)	0.0009 (16)
C14	0.021 (2)	0.0157 (19)	0.0084 (17)	−0.0046 (17)	−0.0013 (15)	0.0056 (16)
C15	0.040 (3)	0.0109 (18)	0.016 (2)	−0.004 (2)	−0.0075 (19)	0.0014 (17)
C16	0.022 (2)	0.0233 (19)	0.0149 (17)	0.0123 (19)	−0.0005 (16)	−0.0047 (16)
C17	0.019 (2)	0.033 (2)	0.0148 (17)	−0.0004 (19)	0.0023 (16)	−0.0020 (18)
C18	0.021 (3)	0.0165 (18)	0.0181 (19)	−0.0017 (17)	0.0040 (16)	−0.0027 (16)
C19	0.015 (2)	0.0198 (18)	0.0123 (16)	−0.004 (2)	−0.0052 (18)	−0.0017 (13)
C20	0.013 (2)	0.0158 (19)	0.018 (2)	−0.0073 (17)	0.0002 (15)	−0.0055 (17)

Geometric parameters (Å, º)

Br1—C19	1.910 (3)	C9—H9	0.9500
C1—C6	1.392 (5)	C10—C11	1.382 (5)
C1—C2	1.398 (5)	C10—H10	0.9500
C1—C19	1.483 (5)	C11—C12	1.380 (5)
C2—C3	1.388 (5)	C11—H11	0.9500
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.385 (5)	C13—C18	1.391 (5)
C3—H3	0.9500	C13—C14	1.391 (5)
C4—C5	1.376 (6)	C13—C20	1.497 (5)
C4—H4	0.9500	C14—C15	1.391 (6)
C5—C6	1.392 (5)	C14—H14	0.9500
C5—H5	0.9500	C15—C16	1.382 (6)
C6—H6	0.9500	C15—H15	0.9500
C7—C12	1.398 (5)	C16—C17	1.384 (6)
C7—C8	1.400 (5)	C16—H16	0.9500
C7—C20	1.508 (5)	C17—C18	1.385 (5)
C8—C9	1.389 (5)	C17—H17	0.9500
C8—H8	0.9500	C18—H18	0.9500
C9—C10	1.392 (5)	C19—C20	1.339 (5)
C6—C1—C2	118.6 (3)	C12—C11—C10	120.3 (4)
C6—C1—C19	119.0 (3)	C12—C11—H11	119.9
C2—C1—C19	122.3 (3)	C10—C11—H11	119.9
C3—C2—C1	120.4 (4)	C11—C12—C7	120.8 (3)
C3—C2—H2	119.8	C11—C12—H12	119.6
C1—C2—H2	119.8	C7—C12—H12	119.6
C4—C3—C2	120.4 (4)	C18—C13—C14	119.0 (4)
C4—C3—H3	119.8	C18—C13—C20	120.0 (3)
C2—C3—H3	119.8	C14—C13—C20	120.8 (3)
C5—C4—C3	119.5 (4)	C15—C14—C13	120.3 (4)
C5—C4—H4	120.2	C15—C14—H14	119.8
C3—C4—H4	120.2	C13—C14—H14	119.8
C4—C5—C6	120.6 (4)	C16—C15—C14	120.1 (4)
C4—C5—H5	119.7	C16—C15—H15	119.9
C6—C5—H5	119.7	C14—C15—H15	119.9
C5—C6—C1	120.5 (4)	C17—C16—C15	119.9 (4)
C5—C6—H6	119.8	C17—C16—H16	120.1
C1—C6—H6	119.8	C15—C16—H16	120.1
C12—C7—C8	118.3 (3)	C16—C17—C18	120.1 (4)
C12—C7—C20	118.8 (3)	C16—C17—H17	119.9
C8—C7—C20	122.9 (3)	C18—C17—H17	119.9
C9—C8—C7	121.0 (4)	C17—C18—C13	120.5 (4)
C9—C8—H8	119.5	C17—C18—H18	119.7
C7—C8—H8	119.5	C13—C18—H18	119.7
C10—C9—C8	119.5 (3)	C20—C19—C1	127.3 (3)
C10—C9—H9	120.3	C20—C19—Br1	119.3 (3)
C8—C9—H9	120.3	C1—C19—Br1	113.3 (3)
C11—C10—C9	120.2 (3)	C19—C20—C13	122.8 (3)
C11—C10—H10	119.9	C19—C20—C7	121.8 (3)
C9—C10—H10	119.9	C13—C20—C7	115.4 (3)
C6—C1—C2—C3	0.9 (5)	C15—C16—C17—C18	0.8 (6)
C19—C1—C2—C3	177.2 (3)	C16—C17—C18—C13	−1.3 (6)
C1—C2—C3—C4	−0.6 (6)	C14—C13—C18—C17	0.7 (6)
C2—C3—C4—C5	−0.3 (6)	C20—C13—C18—C17	−175.6 (4)
C3—C4—C5—C6	0.9 (6)	C6—C1—C19—C20	−48.4 (6)
C4—C5—C6—C1	−0.6 (6)	C2—C1—C19—C20	135.3 (5)
C2—C1—C6—C5	−0.3 (5)	C6—C1—C19—Br1	129.6 (3)
C19—C1—C6—C5	−176.7 (3)	C2—C1—C19—Br1	−46.7 (5)
C12—C7—C8—C9	−1.0 (5)	C1—C19—C20—C13	166.2 (4)
C20—C7—C8—C9	−177.1 (3)	Br1—C19—C20—C13	−11.7 (6)
C7—C8—C9—C10	0.7 (5)	C1—C19—C20—C7	−12.5 (6)
C8—C9—C10—C11	−0.4 (5)	Br1—C19—C20—C7	169.5 (3)
C9—C10—C11—C12	0.6 (6)	C18—C13—C20—C19	−62.8 (5)
C10—C11—C12—C7	−1.0 (6)	C14—C13—C20—C19	120.9 (4)
C8—C7—C12—C11	1.2 (5)	C18—C13—C20—C7	116.0 (4)
C20—C7—C12—C11	177.4 (3)	C14—C13—C20—C7	−60.3 (5)
C18—C13—C14—C15	0.3 (6)	C12—C7—C20—C19	144.4 (4)
C20—C13—C14—C15	176.5 (4)	C8—C7—C20—C19	−39.5 (6)
C13—C14—C15—C16	−0.8 (6)	C12—C7—C20—C13	−34.4 (5)
C14—C15—C16—C17	0.2 (6)	C8—C7—C20—C13	141.6 (4)

(Br2) (2-Bromo-1,2-diphenylethenyl)benzene

Crystal data

C20H15Br	F(000) = 680
Mr = 335.23	Dx = 1.482 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4168 reflections
a = 5.6011 (3) Å	θ = 3.5–27.5°
b = 8.5219 (4) Å	µ = 2.73 mm^−1
c = 31.4741 (13) Å	T = 100 K
V = 1502.32 (12) Å^3	Prism, colorless
Z = 4	0.51 × 0.39 × 0.23 mm

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	3479 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3169 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.034
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 3.1°
ω scan	h = −7→7
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −10→11
Tmin = 0.392, Tmax = 0.619	l = −38→40
10235 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.076	w = 1/[σ^2(Fo^2) + (0.0336P)^2 + 0.9819P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3479 reflections	Δρmax = 0.96 e Å^−3
190 parameters	Δρmin = −0.67 e Å^−3
0 restraints	Absolute structure: Flack parameter from 1425 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.009 (11)

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

	x	y	z	Uiso*/Ueq
Br1	1.00584 (6)	0.15222 (3)	0.208411 (7)	0.02008 (9)
C1	1.0534 (5)	0.0467 (3)	0.12299 (9)	0.0146 (6)
C2	1.2630 (5)	−0.0355 (4)	0.13122 (9)	0.0187 (6)
H2	1.3675	−0.0010	0.1531	0.022*
C3	1.3195 (5)	−0.1679 (4)	0.10758 (10)	0.0192 (6)
H3	1.4636	−0.2230	0.1132	0.023*
C4	1.1685 (6)	−0.2202 (4)	0.07592 (10)	0.0205 (7)
H4	1.2090	−0.3104	0.0597	0.025*
C5	0.9572 (5)	−0.1405 (4)	0.06790 (9)	0.0188 (6)
H5	0.8510	−0.1774	0.0466	0.023*
C6	0.9014 (5)	−0.0076 (3)	0.09088 (9)	0.0161 (6)
H6	0.7581	0.0478	0.0849	0.019*
C7	0.9118 (5)	0.3675 (3)	0.08774 (9)	0.0146 (6)
C8	1.1095 (5)	0.3332 (3)	0.06236 (10)	0.0165 (6)
H8	1.2392	0.2755	0.0740	0.020*
C9	1.1187 (5)	0.3827 (3)	0.02032 (9)	0.0166 (6)
H9	1.2539	0.3582	0.0033	0.020*
C10	0.9306 (5)	0.4678 (4)	0.00302 (9)	0.0178 (7)
H10	0.9370	0.5022	−0.0257	0.021*
C11	0.7341 (5)	0.5018 (3)	0.02801 (10)	0.0159 (6)
H11	0.6046	0.5594	0.0163	0.019*
C12	0.7241 (5)	0.4528 (4)	0.06990 (9)	0.0151 (6)
H12	0.5883	0.4775	0.0867	0.018*
C13	0.7793 (5)	0.4409 (4)	0.16237 (9)	0.0155 (6)
C14	0.8700 (6)	0.5916 (4)	0.16623 (9)	0.0170 (6)
H14	1.0137	0.6190	0.1520	0.020*
C15	0.7520 (6)	0.7030 (4)	0.19081 (10)	0.0231 (7)
H15	0.8163	0.8057	0.1936	0.028*
C16	0.5413 (5)	0.6645 (4)	0.21116 (9)	0.0237 (7)
H16	0.4605	0.7406	0.2279	0.028*
C17	0.4482 (5)	0.5147 (4)	0.20709 (9)	0.0243 (7)
H17	0.3030	0.4880	0.2209	0.029*
C18	0.5661 (5)	0.4043 (4)	0.18296 (9)	0.0201 (7)
H18	0.5012	0.3018	0.1803	0.024*
C19	0.9788 (6)	0.1862 (3)	0.14833 (8)	0.0169 (6)
C20	0.8967 (5)	0.3231 (4)	0.13384 (9)	0.0163 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02878 (16)	0.01962 (13)	0.01185 (12)	−0.00012 (17)	0.00068 (17)	0.00180 (10)
C1	0.0134 (15)	0.0128 (12)	0.0175 (12)	−0.0034 (10)	0.0027 (11)	0.0012 (11)
C2	0.0191 (15)	0.0233 (16)	0.0138 (14)	−0.0017 (13)	−0.0017 (12)	0.0024 (13)
C3	0.0165 (14)	0.0195 (16)	0.0216 (15)	0.0048 (13)	0.0052 (12)	0.0069 (13)
C4	0.0274 (18)	0.0141 (15)	0.0199 (16)	−0.0071 (14)	0.0086 (14)	0.0006 (13)
C5	0.0193 (17)	0.0184 (14)	0.0186 (13)	−0.0078 (13)	0.0017 (12)	0.0014 (11)
C6	0.0153 (13)	0.0139 (15)	0.0192 (14)	−0.0043 (11)	−0.0014 (12)	0.0052 (12)
C7	0.0146 (13)	0.0133 (14)	0.0160 (13)	−0.0052 (11)	−0.0016 (11)	0.0004 (12)
C8	0.0173 (14)	0.0097 (14)	0.0224 (15)	0.0013 (12)	−0.0035 (12)	0.0015 (12)
C9	0.0179 (15)	0.0150 (15)	0.0170 (14)	−0.0016 (12)	0.0047 (12)	−0.0052 (12)
C10	0.0242 (17)	0.0170 (14)	0.0123 (12)	−0.0045 (12)	−0.0005 (11)	−0.0003 (12)
C11	0.0130 (14)	0.0149 (15)	0.0197 (15)	0.0007 (11)	−0.0064 (12)	0.0012 (12)
C12	0.0110 (14)	0.0160 (14)	0.0181 (14)	−0.0020 (12)	0.0007 (12)	−0.0027 (12)
C13	0.0162 (15)	0.0166 (15)	0.0137 (14)	0.0002 (12)	0.0011 (12)	−0.0004 (12)
C14	0.0222 (16)	0.0197 (15)	0.0093 (12)	−0.0057 (12)	−0.0017 (12)	0.0029 (11)
C15	0.038 (2)	0.0129 (14)	0.0184 (15)	−0.0039 (14)	−0.0040 (15)	0.0014 (13)
C16	0.0264 (17)	0.0269 (15)	0.0179 (13)	0.0107 (14)	−0.0017 (14)	−0.0049 (13)
C17	0.0196 (16)	0.0321 (17)	0.0212 (14)	0.0023 (12)	0.0035 (14)	−0.0014 (13)
C18	0.0197 (17)	0.0207 (15)	0.0201 (14)	−0.0027 (12)	0.0028 (12)	0.0006 (12)
C19	0.0143 (14)	0.0224 (14)	0.0139 (12)	−0.0064 (15)	−0.0002 (14)	0.0005 (10)
C20	0.0118 (13)	0.0189 (16)	0.0180 (14)	−0.0059 (12)	0.0002 (12)	−0.0019 (12)

Geometric parameters (Å, º)

Br1—C19	1.919 (3)	C9—H9	0.9500
C1—C2	1.391 (4)	C10—C11	1.384 (4)
C1—C6	1.400 (4)	C10—H10	0.9500
C1—C19	1.491 (4)	C11—C12	1.384 (4)
C2—C3	1.388 (4)	C11—H11	0.9500
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.381 (4)	C13—C14	1.387 (4)
C3—H3	0.9500	C13—C18	1.394 (4)
C4—C5	1.388 (4)	C13—C20	1.498 (4)
C4—H4	0.9500	C14—C15	1.392 (4)
C5—C6	1.380 (4)	C14—H14	0.9500
C5—H5	0.9500	C15—C16	1.383 (5)
C6—H6	0.9500	C15—H15	0.9500
C7—C12	1.396 (4)	C16—C17	1.385 (5)
C7—C8	1.396 (4)	C16—H16	0.9500
C7—C20	1.502 (4)	C17—C18	1.377 (4)
C8—C9	1.390 (4)	C17—H17	0.9500
C8—H8	0.9500	C18—H18	0.9500
C9—C10	1.390 (4)	C19—C20	1.335 (4)
C2—C1—C6	118.7 (3)	C10—C11—C12	120.7 (3)
C2—C1—C19	122.6 (3)	C10—C11—H11	119.7
C6—C1—C19	118.6 (3)	C12—C11—H11	119.7
C3—C2—C1	120.1 (3)	C11—C12—C7	120.7 (3)
C3—C2—H2	119.9	C11—C12—H12	119.7
C1—C2—H2	119.9	C7—C12—H12	119.7
C4—C3—C2	120.6 (3)	C14—C13—C18	118.7 (3)
C4—C3—H3	119.7	C14—C13—C20	120.8 (3)
C2—C3—H3	119.7	C18—C13—C20	120.3 (3)
C3—C4—C5	119.7 (3)	C13—C14—C15	120.4 (3)
C3—C4—H4	120.2	C13—C14—H14	119.8
C5—C4—H4	120.2	C15—C14—H14	119.8
C6—C5—C4	120.0 (3)	C16—C15—C14	120.0 (3)
C6—C5—H5	120.0	C16—C15—H15	120.0
C4—C5—H5	120.0	C14—C15—H15	120.0
C5—C6—C1	120.8 (3)	C15—C16—C17	119.9 (3)
C5—C6—H6	119.6	C15—C16—H16	120.1
C1—C6—H6	119.6	C17—C16—H16	120.1
C12—C7—C8	118.4 (3)	C18—C17—C16	120.0 (3)
C12—C7—C20	118.5 (3)	C18—C17—H17	120.0
C8—C7—C20	123.0 (3)	C16—C17—H17	120.0
C9—C8—C7	120.7 (3)	C17—C18—C13	121.0 (3)
C9—C8—H8	119.7	C17—C18—H18	119.5
C7—C8—H8	119.7	C13—C18—H18	119.5
C10—C9—C8	120.2 (3)	C20—C19—C1	127.6 (2)
C10—C9—H9	119.9	C20—C19—Br1	119.7 (2)
C8—C9—H9	119.9	C1—C19—Br1	112.63 (19)
C11—C10—C9	119.3 (3)	C19—C20—C13	122.1 (3)
C11—C10—H10	120.3	C19—C20—C7	122.0 (3)
C9—C10—H10	120.3	C13—C20—C7	115.8 (3)
C6—C1—C2—C3	0.6 (4)	C15—C16—C17—C18	0.3 (4)
C19—C1—C2—C3	177.7 (3)	C16—C17—C18—C13	0.0 (5)
C1—C2—C3—C4	−0.5 (4)	C14—C13—C18—C17	−0.7 (4)
C2—C3—C4—C5	−0.5 (4)	C20—C13—C18—C17	−175.8 (3)
C3—C4—C5—C6	1.4 (4)	C2—C1—C19—C20	134.3 (3)
C4—C5—C6—C1	−1.3 (4)	C6—C1—C19—C20	−48.6 (4)
C2—C1—C6—C5	0.3 (4)	C2—C1—C19—Br1	−46.7 (3)
C19—C1—C6—C5	−176.9 (3)	C6—C1—C19—Br1	130.4 (2)
C12—C7—C8—C9	−0.2 (4)	C1—C19—C20—C13	166.6 (3)
C20—C7—C8—C9	−177.3 (3)	Br1—C19—C20—C13	−12.3 (4)
C7—C8—C9—C10	0.3 (4)	C1—C19—C20—C7	−12.1 (5)
C8—C9—C10—C11	−0.4 (4)	Br1—C19—C20—C7	169.0 (2)
C9—C10—C11—C12	0.4 (4)	C14—C13—C20—C19	121.6 (3)
C10—C11—C12—C7	−0.3 (5)	C18—C13—C20—C19	−63.4 (4)
C8—C7—C12—C11	0.2 (4)	C14—C13—C20—C7	−59.6 (4)
C20—C7—C12—C11	177.4 (3)	C18—C13—C20—C7	115.4 (3)
C18—C13—C14—C15	1.1 (4)	C12—C7—C20—C19	143.5 (3)
C20—C13—C14—C15	176.2 (3)	C8—C7—C20—C19	−39.4 (4)
C13—C14—C15—C16	−0.8 (5)	C12—C7—C20—C13	−35.2 (4)
C14—C15—C16—C17	0.1 (5)	C8—C7—C20—C13	141.8 (3)

(Br3) (2-Bromo-1,2-diphenylethenyl)benzene

Crystal data

C20H15Br	F(000) = 680
Mr = 335.23	Dx = 1.479 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3648 reflections
a = 5.6104 (4) Å	θ = 3.5–27.5°
b = 8.5238 (4) Å	µ = 2.72 mm^−1
c = 31.496 (2) Å	T = 100 K
V = 1506.20 (17) Å^3	Prism, colorless
Z = 4	0.44 × 0.27 × 0.22 mm

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	3486 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3018 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.047
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 3.1°
ω scan	h = −4→7
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −11→11
Tmin = 0.460, Tmax = 0.633	l = −40→36
8919 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0332P)^2 + 1.2196P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3486 reflections	Δρmax = 1.13 e Å^−3
190 parameters	Δρmin = −0.96 e Å^−3
0 restraints	Absolute structure: Flack parameter from 1416 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.015 (15)

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

	x	y	z	Uiso*/Ueq
Br1	1.00606 (10)	0.15237 (4)	0.208402 (10)	0.02145 (12)
C1	1.0542 (7)	0.0481 (4)	0.12302 (11)	0.0155 (9)
C2	1.2641 (8)	−0.0348 (5)	0.13111 (12)	0.0193 (9)
H2	1.3691	−0.0002	0.1528	0.023*
C3	1.3203 (8)	−0.1680 (5)	0.10752 (12)	0.0206 (9)
H3	1.4641	−0.2232	0.1131	0.025*
C4	1.1677 (9)	−0.2202 (5)	0.07604 (13)	0.0201 (9)
H4	1.2072	−0.3110	0.0600	0.024*
C5	0.9569 (8)	−0.1403 (4)	0.06771 (11)	0.0188 (9)
H5	0.8517	−0.1766	0.0462	0.023*
C6	0.9014 (7)	−0.0074 (4)	0.09102 (12)	0.0155 (8)
H6	0.7574	0.0473	0.0853	0.019*
C7	0.9114 (7)	0.3679 (4)	0.08752 (12)	0.0148 (8)
C8	1.1099 (7)	0.3344 (5)	0.06224 (13)	0.0182 (8)
H8	1.2402	0.2780	0.0740	0.022*
C9	1.1189 (8)	0.3827 (4)	0.02018 (12)	0.0172 (9)
H9	1.2538	0.3580	0.0032	0.021*
C10	0.9306 (8)	0.4671 (5)	0.00296 (11)	0.0178 (10)
H10	0.9354	0.5006	−0.0258	0.021*
C11	0.7360 (7)	0.5016 (5)	0.02821 (13)	0.0176 (9)
H11	0.6070	0.5595	0.0165	0.021*
C12	0.7250 (7)	0.4544 (5)	0.06969 (12)	0.0168 (9)
H12	0.5899	0.4805	0.0864	0.020*
C13	0.7794 (8)	0.4418 (5)	0.16238 (12)	0.0164 (9)
C14	0.8716 (8)	0.5929 (5)	0.16637 (12)	0.0184 (9)
H14	1.0159	0.6198	0.1523	0.022*
C15	0.7530 (9)	0.7049 (5)	0.19087 (13)	0.0263 (11)
H15	0.8162	0.8078	0.1937	0.032*
C16	0.5413 (8)	0.6643 (5)	0.21108 (11)	0.0252 (10)
H16	0.4601	0.7401	0.2278	0.030*
C17	0.4478 (8)	0.5149 (5)	0.20711 (12)	0.0239 (10)
H17	0.3024	0.4883	0.2208	0.029*
C18	0.5676 (8)	0.4044 (5)	0.18300 (12)	0.0210 (10)
H18	0.5043	0.3015	0.1805	0.025*
C19	0.9801 (9)	0.1863 (4)	0.14851 (11)	0.0190 (8)
C20	0.8969 (7)	0.3238 (5)	0.13404 (12)	0.0178 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0292 (2)	0.02100 (18)	0.01411 (16)	0.0012 (3)	0.0010 (2)	0.00171 (14)
C1	0.013 (3)	0.0138 (16)	0.0196 (17)	0.0022 (16)	0.0028 (16)	0.0031 (16)
C2	0.021 (3)	0.022 (2)	0.0146 (18)	−0.0012 (19)	−0.0006 (17)	0.0006 (18)
C3	0.018 (2)	0.019 (2)	0.025 (2)	0.0061 (19)	0.0045 (17)	0.0087 (19)
C4	0.023 (3)	0.0124 (18)	0.025 (2)	−0.0036 (19)	0.0081 (19)	0.0004 (18)
C5	0.018 (3)	0.0187 (17)	0.0201 (17)	−0.004 (2)	0.0034 (16)	−0.0005 (16)
C6	0.011 (2)	0.0107 (17)	0.024 (2)	−0.0054 (16)	0.0010 (16)	0.0047 (17)
C7	0.012 (2)	0.0135 (18)	0.0192 (18)	−0.0047 (16)	−0.0018 (15)	0.0031 (17)
C8	0.014 (2)	0.0174 (19)	0.0230 (19)	0.0010 (18)	−0.0022 (16)	−0.0005 (19)
C9	0.016 (2)	0.0153 (19)	0.0203 (19)	−0.0021 (17)	0.0046 (16)	−0.0056 (17)
C10	0.024 (3)	0.0149 (18)	0.0142 (16)	−0.0039 (17)	0.0015 (16)	0.0009 (16)
C11	0.011 (2)	0.0148 (19)	0.027 (2)	0.0023 (16)	−0.0089 (17)	−0.0020 (18)
C12	0.009 (2)	0.0196 (19)	0.0213 (19)	−0.0003 (18)	0.0019 (16)	−0.0042 (18)
C13	0.017 (2)	0.0191 (19)	0.0132 (18)	0.0043 (18)	0.0034 (16)	0.0025 (17)
C14	0.023 (3)	0.0196 (19)	0.0127 (17)	−0.0019 (17)	−0.0017 (17)	0.0035 (16)
C15	0.045 (3)	0.0150 (19)	0.019 (2)	−0.004 (2)	−0.008 (2)	−0.0002 (18)
C16	0.031 (3)	0.0266 (19)	0.0184 (17)	0.012 (2)	0.0001 (19)	−0.0025 (17)
C17	0.016 (3)	0.033 (2)	0.0221 (18)	0.0049 (18)	0.0023 (18)	−0.0016 (19)
C18	0.018 (3)	0.0207 (19)	0.025 (2)	0.0005 (17)	0.0016 (17)	−0.0009 (17)
C19	0.015 (2)	0.0237 (18)	0.0182 (16)	0.000 (2)	−0.001 (2)	−0.0022 (14)
C20	0.007 (2)	0.021 (2)	0.025 (2)	−0.0045 (17)	0.0004 (16)	0.0005 (18)

Geometric parameters (Å, º)

Br1—C19	1.914 (3)	C9—H9	0.9500
C1—C2	1.397 (6)	C10—C11	1.382 (6)
C1—C6	1.405 (5)	C10—H10	0.9500
C1—C19	1.486 (5)	C11—C12	1.369 (6)
C2—C3	1.393 (6)	C11—H11	0.9500
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.384 (6)	C13—C18	1.391 (6)
C3—H3	0.9500	C13—C14	1.394 (6)
C4—C5	1.389 (6)	C13—C20	1.497 (5)
C4—H4	0.9500	C14—C15	1.397 (6)
C5—C6	1.386 (5)	C14—H14	0.9500
C5—H5	0.9500	C15—C16	1.391 (6)
C6—H6	0.9500	C15—H15	0.9500
C7—C12	1.397 (6)	C16—C17	1.384 (6)
C7—C8	1.399 (5)	C16—H16	0.9500
C7—C20	1.515 (5)	C17—C18	1.384 (5)
C8—C9	1.388 (6)	C17—H17	0.9500
C8—H8	0.9500	C18—H18	0.9500
C9—C10	1.389 (5)	C19—C20	1.341 (5)
C2—C1—C6	118.4 (3)	C12—C11—C10	121.5 (4)
C2—C1—C19	122.6 (4)	C12—C11—H11	119.3
C6—C1—C19	118.9 (4)	C10—C11—H11	119.3
C3—C2—C1	120.4 (4)	C11—C12—C7	120.4 (4)
C3—C2—H2	119.8	C11—C12—H12	119.8
C1—C2—H2	119.8	C7—C12—H12	119.8
C4—C3—C2	120.3 (4)	C18—C13—C14	119.1 (4)
C4—C3—H3	119.9	C18—C13—C20	120.0 (4)
C2—C3—H3	119.9	C14—C13—C20	120.7 (4)
C3—C4—C5	120.3 (4)	C13—C14—C15	120.3 (4)
C3—C4—H4	119.8	C13—C14—H14	119.8
C5—C4—H4	119.8	C15—C14—H14	119.8
C6—C5—C4	119.5 (4)	C16—C15—C14	119.3 (4)
C6—C5—H5	120.3	C16—C15—H15	120.3
C4—C5—H5	120.3	C14—C15—H15	120.3
C5—C6—C1	121.2 (4)	C17—C16—C15	120.8 (4)
C5—C6—H6	119.4	C17—C16—H16	119.6
C1—C6—H6	119.4	C15—C16—H16	119.6
C12—C7—C8	118.4 (4)	C16—C17—C18	119.4 (4)
C12—C7—C20	118.6 (4)	C16—C17—H17	120.3
C8—C7—C20	122.9 (4)	C18—C17—H17	120.3
C9—C8—C7	120.8 (4)	C17—C18—C13	121.0 (4)
C9—C8—H8	119.6	C17—C18—H18	119.5
C7—C8—H8	119.6	C13—C18—H18	119.5
C8—C9—C10	119.9 (4)	C20—C19—C1	127.4 (3)
C8—C9—H9	120.0	C20—C19—Br1	119.6 (3)
C10—C9—H9	120.0	C1—C19—Br1	113.0 (3)
C11—C10—C9	119.1 (3)	C19—C20—C13	122.5 (4)
C11—C10—H10	120.4	C19—C20—C7	121.8 (3)
C9—C10—H10	120.4	C13—C20—C7	115.7 (3)
C6—C1—C2—C3	0.7 (6)	C15—C16—C17—C18	0.5 (6)
C19—C1—C2—C3	177.1 (4)	C16—C17—C18—C13	−0.6 (6)
C1—C2—C3—C4	−0.5 (6)	C14—C13—C18—C17	0.3 (6)
C2—C3—C4—C5	−0.1 (6)	C20—C13—C18—C17	−175.7 (4)
C3—C4—C5—C6	0.4 (6)	C2—C1—C19—C20	134.6 (5)
C4—C5—C6—C1	−0.1 (6)	C6—C1—C19—C20	−49.0 (7)
C2—C1—C6—C5	−0.4 (6)	C2—C1—C19—Br1	−46.7 (5)
C19—C1—C6—C5	−176.9 (3)	C6—C1—C19—Br1	129.6 (3)
C12—C7—C8—C9	−1.5 (6)	C1—C19—C20—C13	166.6 (4)
C20—C7—C8—C9	−177.4 (4)	Br1—C19—C20—C13	−11.9 (6)
C7—C8—C9—C10	0.9 (6)	C1—C19—C20—C7	−12.0 (7)
C8—C9—C10—C11	0.0 (6)	Br1—C19—C20—C7	169.4 (3)
C9—C10—C11—C12	−0.1 (6)	C18—C13—C20—C19	−63.1 (6)
C10—C11—C12—C7	−0.6 (6)	C14—C13—C20—C19	121.0 (5)
C8—C7—C12—C11	1.4 (6)	C18—C13—C20—C7	115.6 (4)
C20—C7—C12—C11	177.4 (4)	C14—C13—C20—C7	−60.3 (5)
C18—C13—C14—C15	0.2 (6)	C12—C7—C20—C19	144.3 (4)
C20—C13—C14—C15	176.2 (4)	C8—C7—C20—C19	−39.9 (6)
C13—C14—C15—C16	−0.3 (6)	C12—C7—C20—C13	−34.4 (5)
C14—C15—C16—C17	−0.1 (6)	C8—C7—C20—C13	141.4 (4)

(Br4) (2-Bromo-1,2-diphenylethenyl)benzene

Crystal data

C20H15Br	F(000) = 680
Mr = 335.23	Dx = 1.479 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3203 reflections
a = 5.6112 (4) Å	θ = 3.5–27.3°
b = 8.5333 (4) Å	µ = 2.72 mm^−1
c = 31.4392 (14) Å	T = 100 K
V = 1505.37 (14) Å^3	Prism, colorless
Z = 4	0.25 × 0.20 × 0.20 mm

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	3454 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3005 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.047
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scan	h = −4→7
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −11→11
Tmin = 0.598, Tmax = 0.647	l = −40→36
8872 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0332P)^2 + 1.2196P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3486 reflections	Δρmax = 1.15 e Å^−3
190 parameters	Δρmin = −0.97 e Å^−3
0 restraints	Absolute structure: Flack parameter from 1416 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.015 (15)

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

	x	y	z	Uiso*/Ueq
Br1	1.00605 (10)	0.15237 (4)	0.208402 (10)	0.02147 (12)
C1	1.0542 (7)	0.0481 (4)	0.12303 (11)	0.0155 (9)
C2	1.2641 (8)	−0.0349 (5)	0.13111 (12)	0.0193 (9)
H2	1.3692	−0.0002	0.1528	0.023*
C3	1.3204 (8)	−0.1680 (5)	0.10752 (12)	0.0207 (9)
H3	1.4641	−0.2231	0.1131	0.025*
C4	1.1677 (9)	−0.2202 (5)	0.07604 (13)	0.0201 (9)
H4	1.2070	−0.3110	0.0600	0.024*
C5	0.9569 (8)	−0.1403 (4)	0.06771 (11)	0.0189 (9)
H5	0.8517	−0.1766	0.0462	0.023*
C6	0.9014 (7)	−0.0074 (4)	0.09102 (12)	0.0156 (9)
H6	0.7574	0.0472	0.0852	0.019*
C7	0.9114 (7)	0.3679 (4)	0.08752 (12)	0.0148 (8)
C8	1.1100 (7)	0.3344 (5)	0.06225 (13)	0.0183 (9)
H8	1.2402	0.2780	0.0740	0.022*
C9	1.1189 (8)	0.3826 (4)	0.02018 (12)	0.0172 (9)
H9	1.2537	0.3580	0.0032	0.021*
C10	0.9306 (8)	0.4670 (5)	0.00296 (11)	0.0178 (10)
H10	0.9355	0.5006	−0.0258	0.021*
C11	0.7360 (7)	0.5016 (5)	0.02820 (13)	0.0176 (9)
H11	0.6071	0.5595	0.0165	0.021*
C12	0.7250 (7)	0.4544 (5)	0.06968 (12)	0.0168 (9)
H12	0.5900	0.4805	0.0865	0.020*
C13	0.7794 (8)	0.4418 (5)	0.16238 (12)	0.0165 (9)
C14	0.8717 (8)	0.5929 (5)	0.16636 (12)	0.0184 (9)
H14	1.0159	0.6197	0.1523	0.022*
C15	0.7530 (9)	0.7049 (5)	0.19087 (13)	0.0263 (11)
H15	0.8162	0.8077	0.1937	0.032*
C16	0.5413 (8)	0.6643 (5)	0.21108 (11)	0.0252 (10)
H16	0.4600	0.7400	0.2278	0.030*
C17	0.4477 (8)	0.5148 (5)	0.20711 (12)	0.0239 (10)
H17	0.3024	0.4883	0.2208	0.029*
C18	0.5677 (8)	0.4044 (5)	0.18300 (12)	0.0210 (10)
H18	0.5044	0.3016	0.1805	0.025*
C19	0.9801 (9)	0.1863 (4)	0.14851 (11)	0.0190 (8)
C20	0.8969 (7)	0.3238 (5)	0.13404 (12)	0.0177 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0293 (2)	0.02108 (18)	0.01405 (16)	0.0012 (3)	0.0010 (2)	0.00171 (14)
C1	0.013 (3)	0.0138 (16)	0.0195 (17)	0.0022 (16)	0.0027 (16)	0.0030 (16)
C2	0.021 (3)	0.022 (2)	0.0145 (18)	−0.0012 (19)	−0.0005 (17)	0.0006 (18)
C3	0.018 (2)	0.019 (2)	0.025 (2)	0.0061 (19)	0.0045 (17)	0.0087 (19)
C4	0.023 (3)	0.0124 (18)	0.025 (2)	−0.0035 (19)	0.0080 (19)	0.0003 (18)
C5	0.018 (3)	0.0188 (17)	0.0201 (17)	−0.004 (2)	0.0033 (16)	−0.0005 (16)
C6	0.011 (2)	0.0108 (18)	0.0244 (19)	−0.0054 (16)	0.0009 (16)	0.0047 (17)
C7	0.012 (2)	0.0136 (18)	0.0191 (18)	−0.0047 (16)	−0.0018 (15)	0.0031 (17)
C8	0.014 (2)	0.0176 (19)	0.0228 (19)	0.0009 (18)	−0.0022 (16)	−0.0005 (19)
C9	0.016 (2)	0.015 (2)	0.0203 (19)	−0.0021 (17)	0.0046 (16)	−0.0057 (17)
C10	0.024 (3)	0.0150 (18)	0.0142 (16)	−0.0039 (17)	0.0015 (16)	0.0009 (16)
C11	0.011 (2)	0.0150 (19)	0.027 (2)	0.0023 (16)	−0.0089 (17)	−0.0020 (18)
C12	0.009 (2)	0.0197 (19)	0.0213 (19)	−0.0003 (18)	0.0019 (16)	−0.0043 (18)
C13	0.017 (2)	0.0192 (19)	0.0131 (18)	0.0044 (18)	0.0034 (16)	0.0024 (17)
C14	0.023 (3)	0.020 (2)	0.0126 (17)	−0.0019 (17)	−0.0017 (17)	0.0035 (16)
C15	0.045 (3)	0.0150 (19)	0.019 (2)	−0.004 (2)	−0.008 (2)	−0.0002 (18)
C16	0.031 (3)	0.0267 (19)	0.0183 (16)	0.012 (2)	0.0000 (19)	−0.0025 (17)
C17	0.016 (3)	0.033 (2)	0.0220 (18)	0.0049 (18)	0.0023 (18)	−0.0016 (19)
C18	0.018 (3)	0.0207 (19)	0.0246 (19)	0.0005 (17)	0.0015 (17)	−0.0009 (17)
C19	0.015 (2)	0.0238 (18)	0.0180 (16)	0.000 (2)	−0.001 (2)	−0.0022 (14)
C20	0.007 (2)	0.021 (2)	0.025 (2)	−0.0046 (17)	0.0004 (16)	0.0005 (18)

Geometric parameters (Å, º)

Br1—C19	1.911 (3)	C9—H9	0.9500
C1—C2	1.397 (6)	C10—C11	1.382 (6)
C1—C6	1.404 (5)	C10—H10	0.9500
C1—C19	1.486 (5)	C11—C12	1.366 (6)
C2—C3	1.393 (6)	C11—H11	0.9500
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.383 (6)	C13—C18	1.390 (6)
C3—H3	0.9500	C13—C14	1.395 (6)
C4—C5	1.389 (6)	C13—C20	1.497 (5)
C4—H4	0.9500	C14—C15	1.397 (6)
C5—C6	1.386 (5)	C14—H14	0.9500
C5—H5	0.9500	C15—C16	1.391 (6)
C6—H6	0.9500	C15—H15	0.9500
C7—C12	1.398 (6)	C16—C17	1.385 (6)
C7—C8	1.398 (5)	C16—H16	0.9500
C7—C20	1.513 (5)	C17—C18	1.384 (5)
C8—C9	1.386 (6)	C17—H17	0.9500
C8—H8	0.9500	C18—H18	0.9500
C9—C10	1.389 (5)	C19—C20	1.342 (5)
C2—C1—C6	118.3 (3)	C12—C11—C10	121.4 (4)
C2—C1—C19	122.7 (4)	C12—C11—H11	119.3
C6—C1—C19	118.9 (4)	C10—C11—H11	119.3
C3—C2—C1	120.5 (4)	C11—C12—C7	120.3 (4)
C3—C2—H2	119.8	C11—C12—H12	119.8
C1—C2—H2	119.8	C7—C12—H12	119.8
C4—C3—C2	120.2 (4)	C18—C13—C14	119.2 (4)
C4—C3—H3	119.9	C18—C13—C20	120.0 (4)
C2—C3—H3	119.9	C14—C13—C20	120.8 (4)
C3—C4—C5	120.3 (4)	C13—C14—C15	120.4 (4)
C3—C4—H4	119.9	C13—C14—H14	119.8
C5—C4—H4	119.9	C15—C14—H14	119.8
C6—C5—C4	119.5 (4)	C16—C15—C14	119.2 (4)
C6—C5—H5	120.2	C16—C15—H15	120.4
C4—C5—H5	120.2	C14—C15—H15	120.4
C5—C6—C1	121.2 (4)	C17—C16—C15	120.8 (4)
C5—C6—H6	119.4	C17—C16—H16	119.6
C1—C6—H6	119.4	C15—C16—H16	119.6
C12—C7—C8	118.5 (4)	C18—C17—C16	119.5 (4)
C12—C7—C20	118.6 (4)	C18—C17—H17	120.3
C8—C7—C20	122.8 (4)	C16—C17—H17	120.3
C9—C8—C7	120.7 (4)	C17—C18—C13	121.0 (4)
C9—C8—H8	119.7	C17—C18—H18	119.5
C7—C8—H8	119.7	C13—C18—H18	119.5
C8—C9—C10	119.9 (4)	C20—C19—C1	127.5 (3)
C8—C9—H9	120.1	C20—C19—Br1	119.6 (3)
C10—C9—H9	120.1	C1—C19—Br1	112.9 (3)
C11—C10—C9	119.2 (3)	C19—C20—C13	122.6 (4)
C11—C10—H10	120.4	C19—C20—C7	121.8 (3)
C9—C10—H10	120.4	C13—C20—C7	115.6 (3)
C6—C1—C2—C3	0.7 (6)	C15—C16—C17—C18	0.5 (6)
C19—C1—C2—C3	177.1 (4)	C16—C17—C18—C13	−0.6 (6)
C1—C2—C3—C4	−0.5 (6)	C14—C13—C18—C17	0.3 (6)
C2—C3—C4—C5	−0.1 (6)	C20—C13—C18—C17	−175.7 (4)
C3—C4—C5—C6	0.4 (6)	C2—C1—C19—C20	134.6 (5)
C4—C5—C6—C1	−0.1 (6)	C6—C1—C19—C20	−49.1 (7)
C2—C1—C6—C5	−0.4 (6)	C2—C1—C19—Br1	−46.8 (5)
C19—C1—C6—C5	−176.9 (3)	C6—C1—C19—Br1	129.5 (3)
C12—C7—C8—C9	−1.6 (6)	C1—C19—C20—C13	166.6 (4)
C20—C7—C8—C9	−177.4 (4)	Br1—C19—C20—C13	−12.0 (6)
C7—C8—C9—C10	0.9 (6)	C1—C19—C20—C7	−12.0 (7)
C8—C9—C10—C11	−0.1 (6)	Br1—C19—C20—C7	169.4 (3)
C9—C10—C11—C12	−0.1 (6)	C18—C13—C20—C19	−63.1 (6)
C10—C11—C12—C7	−0.6 (6)	C14—C13—C20—C19	121.0 (5)
C8—C7—C12—C11	1.4 (6)	C18—C13—C20—C7	115.6 (4)
C20—C7—C12—C11	177.4 (4)	C14—C13—C20—C7	−60.3 (5)
C18—C13—C14—C15	0.2 (6)	C12—C7—C20—C19	144.3 (4)
C20—C13—C14—C15	176.2 (4)	C8—C7—C20—C19	−39.9 (6)
C13—C14—C15—C16	−0.3 (6)	C12—C7—C20—C13	−34.4 (5)
C14—C15—C16—C17	0.0 (6)	C8—C7—C20—C13	141.4 (4)

(Cu1) Diaquabis(3,5-dinitrobenzoato)[1,3,5,7- tetraazatricyclo[3.3.1.1^3,7]decane]copper(II) dihydrate

Crystal data

Cu(H2O)2(C6H12N4)(C7H3N2O6)2·2H2O	F(000) = 1436
Mr = 698.03	Dx = 1.838 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6228 reflections
a = 23.0024 (11) Å	θ = 3.5–27.8°
b = 8.9753 (4) Å	µ = 0.97 mm^−1
c = 12.3386 (5) Å	T = 100 K
β = 98.041 (4)°	Block, blue
V = 2522.30 (19) Å^3	0.85 × 0.66 × 0.38 mm
Z = 4

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	2912 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2556 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.041
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 2.9°
ω scan	h = −27→29
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −11→11
Tmin = 0.516, Tmax = 0.730	l = −15→16
13102 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.075	w = 1/[σ^2(Fo^2) + (0.0373P)^2 + 2.2802P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2912 reflections	Δρmax = 0.43 e Å^−3
223 parameters	Δρmin = −0.48 e Å^−3
4 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0073 (4)

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.5000	0.5000	0.5000	0.00584 (11)
O1	0.58521 (5)	0.51213 (12)	0.53212 (9)	0.0083 (2)
O2	0.61853 (5)	0.34884 (13)	0.41704 (10)	0.0137 (3)
O3	0.82857 (6)	0.37419 (15)	0.37993 (10)	0.0193 (3)
O4	0.88893 (6)	0.47924 (14)	0.50746 (11)	0.0166 (3)
O5	0.80883 (5)	0.85976 (13)	0.72015 (9)	0.0122 (3)
O6	0.72401 (5)	0.81747 (14)	0.77216 (10)	0.0143 (3)
O1W	0.50058 (6)	0.72998 (13)	0.58498 (10)	0.0119 (3)
O2W	0.59272 (6)	0.84111 (15)	0.73267 (11)	0.0187 (3)
N1	0.83947 (6)	0.44802 (16)	0.46403 (11)	0.0105 (3)
N2	0.76262 (6)	0.79012 (15)	0.71609 (11)	0.0087 (3)
N3	0.50043 (6)	0.62980 (14)	0.35011 (10)	0.0067 (3)
N4	0.44656 (6)	0.82434 (15)	0.23693 (11)	0.0089 (3)
C1	0.62526 (7)	0.44761 (18)	0.48769 (12)	0.0083 (3)
C2	0.68664 (7)	0.50449 (16)	0.52659 (13)	0.0077 (3)
C3	0.73371 (7)	0.44790 (18)	0.48007 (13)	0.0084 (3)
H3	0.7277	0.3728	0.4253	0.010*
C4	0.78940 (8)	0.50278 (17)	0.51486 (13)	0.0088 (3)
C5	0.80081 (7)	0.61206 (17)	0.59433 (13)	0.0086 (3)
H5	0.8394	0.6472	0.6182	0.010*
C6	0.75259 (7)	0.66682 (17)	0.63667 (12)	0.0081 (3)
C7	0.69606 (7)	0.61615 (17)	0.60594 (12)	0.0081 (3)
H7	0.6643	0.6563	0.6380	0.010*
C8	0.5000	0.5369 (2)	0.2500	0.0072 (4)
H8A	0.4649	0.4720	0.2413	0.009*	0.50
H8B	0.5351	0.4720	0.2587	0.009*	0.50
C9	0.44741 (7)	0.72904 (17)	0.33329 (12)	0.0080 (3)
H9A	0.4115	0.6667	0.3248	0.010*
H9B	0.4470	0.7923	0.3989	0.010*
C10	0.44674 (7)	0.72853 (17)	0.14074 (12)	0.0083 (3)
H10A	0.4457	0.7917	0.0747	0.010*
H10B	0.4109	0.6661	0.1316	0.010*
C11	0.5000	0.9164 (2)	0.2500	0.0102 (5)
H11A	0.5003	0.9812	0.3150	0.012*	0.50
H11B	0.4997	0.9812	0.1850	0.012*	0.50
H11	0.4677 (6)	0.745 (3)	0.6041 (18)	0.029 (6)*
H12	0.5281 (7)	0.758 (2)	0.6314 (14)	0.020 (6)*
H21	0.6106 (11)	0.794 (3)	0.7855 (15)	0.045 (8)*
H22	0.5986 (12)	0.9322 (12)	0.741 (2)	0.045 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.00323 (16)	0.00784 (16)	0.00655 (16)	−0.00042 (9)	0.00107 (10)	0.00009 (9)
O1	0.0038 (6)	0.0113 (6)	0.0098 (6)	0.0003 (4)	0.0013 (4)	0.0009 (4)
O2	0.0099 (6)	0.0163 (6)	0.0150 (6)	−0.0030 (5)	0.0022 (5)	−0.0062 (5)
O3	0.0118 (7)	0.0289 (7)	0.0178 (7)	0.0005 (5)	0.0035 (5)	−0.0130 (5)
O4	0.0044 (6)	0.0196 (7)	0.0257 (7)	−0.0018 (5)	0.0017 (5)	−0.0081 (5)
O5	0.0107 (6)	0.0127 (6)	0.0127 (6)	−0.0036 (5)	0.0006 (5)	−0.0014 (4)
O6	0.0104 (7)	0.0183 (6)	0.0148 (6)	0.0019 (5)	0.0045 (5)	−0.0062 (5)
O1W	0.0084 (7)	0.0147 (6)	0.0130 (6)	−0.0008 (5)	0.0027 (5)	−0.0028 (4)
O2W	0.0165 (7)	0.0186 (7)	0.0188 (7)	0.0024 (5)	−0.0052 (5)	−0.0002 (5)
N1	0.0068 (7)	0.0118 (7)	0.0131 (7)	0.0009 (5)	0.0017 (5)	−0.0019 (5)
N2	0.0084 (7)	0.0088 (7)	0.0085 (6)	0.0008 (5)	−0.0004 (5)	−0.0001 (5)
N3	0.0049 (7)	0.0074 (6)	0.0075 (6)	−0.0004 (5)	0.0005 (5)	−0.0006 (5)
N4	0.0090 (7)	0.0090 (7)	0.0089 (6)	0.0008 (5)	0.0025 (5)	−0.0002 (5)
C1	0.0072 (8)	0.0091 (8)	0.0087 (7)	0.0014 (6)	0.0017 (6)	0.0033 (6)
C2	0.0067 (9)	0.0087 (8)	0.0074 (7)	−0.0006 (6)	0.0003 (6)	0.0030 (5)
C3	0.0095 (8)	0.0070 (7)	0.0086 (7)	−0.0001 (6)	0.0013 (6)	0.0015 (6)
C4	0.0062 (8)	0.0102 (8)	0.0106 (8)	0.0016 (6)	0.0033 (6)	0.0018 (5)
C5	0.0065 (8)	0.0083 (8)	0.0107 (7)	−0.0006 (6)	0.0002 (6)	0.0017 (6)
C6	0.0096 (8)	0.0073 (8)	0.0072 (7)	0.0003 (6)	0.0004 (6)	0.0004 (5)
C7	0.0079 (8)	0.0096 (8)	0.0074 (7)	0.0021 (6)	0.0027 (6)	0.0023 (5)
C8	0.0073 (12)	0.0054 (10)	0.0090 (11)	0.000	0.0017 (8)	0.000
C9	0.0054 (8)	0.0099 (8)	0.0091 (7)	0.0012 (6)	0.0021 (6)	0.0008 (6)
C10	0.0075 (8)	0.0085 (8)	0.0088 (7)	0.0026 (6)	0.0010 (6)	−0.0002 (5)
C11	0.0122 (12)	0.0062 (11)	0.0124 (11)	0.000	0.0032 (9)	0.000

Geometric parameters (Å, º)

Cu1—O1^i	1.9476 (12)	N4—C11	1.4709 (18)
Cu1—O1	1.9476 (12)	C1—C2	1.515 (2)
Cu1—N3^i	2.1869 (13)	C2—C3	1.391 (2)
Cu1—N3	2.1869 (13)	C2—C7	1.397 (2)
Cu1—O1W^i	2.3143 (12)	C3—C4	1.384 (2)
Cu1—O1W	2.3143 (12)	C3—H3	0.9500
O1—C1	1.275 (2)	C4—C5	1.386 (2)
O2—C1	1.238 (2)	C5—C6	1.381 (2)
O3—N1	1.2272 (18)	C5—H5	0.9500
O4—N1	1.2205 (19)	C6—C7	1.380 (2)
O5—N2	1.2282 (18)	C7—H7	0.9500
O6—N2	1.2246 (18)	C8—N3^ii	1.4894 (17)
O1W—H11	0.834 (10)	C8—H8A	0.9900
O1W—H12	0.831 (10)	C8—H8B	0.9900
O2W—H21	0.834 (10)	C9—H9A	0.9900
O2W—H22	0.833 (10)	C9—H9B	0.9900
N1—C4	1.471 (2)	C10—N3^ii	1.496 (2)
N2—C6	1.475 (2)	C10—H10A	0.9900
N3—C8	1.4894 (17)	C10—H10B	0.9900
N3—C10^ii	1.496 (2)	C11—N4^ii	1.4709 (18)
N3—C9	1.501 (2)	C11—H11A	0.9900
N4—C9	1.4626 (19)	C11—H11B	0.9900
N4—C10	1.4661 (19)
O1^i—Cu1—O1	180.000 (15)	C7—C2—C1	120.68 (15)
O1^i—Cu1—N3^i	91.08 (5)	C4—C3—C2	118.85 (15)
O1—Cu1—N3^i	88.92 (5)	C4—C3—H3	120.6
O1^i—Cu1—N3	88.92 (5)	C2—C3—H3	120.6
O1—Cu1—N3	91.08 (5)	C3—C4—C5	123.16 (16)
N3^i—Cu1—N3	180.0	C3—C4—N1	119.66 (14)
O1^i—Cu1—O1W^i	85.19 (4)	C5—C4—N1	117.15 (15)
O1—Cu1—O1W^i	94.81 (4)	C6—C5—C4	115.92 (15)
N3^i—Cu1—O1W^i	84.70 (4)	C6—C5—H5	122.0
N3—Cu1—O1W^i	95.30 (4)	C4—C5—H5	122.0
O1^i—Cu1—O1W	94.81 (4)	C7—C6—C5	123.69 (15)
O1—Cu1—O1W	85.19 (4)	C7—C6—N2	118.93 (14)
N3^i—Cu1—O1W	95.30 (4)	C5—C6—N2	117.33 (14)
N3—Cu1—O1W	84.70 (4)	C6—C7—C2	118.49 (15)
O1W^i—Cu1—O1W	180.0	C6—C7—H7	120.8
C1—O1—Cu1	130.86 (11)	C2—C7—H7	120.8
Cu1—O1W—H11	109.0 (16)	N3—C8—N3^ii	111.89 (17)
Cu1—O1W—H12	122.7 (15)	N3—C8—H8A	109.2
H11—O1W—H12	113 (2)	N3^ii—C8—H8A	109.2
H21—O2W—H22	110 (3)	N3—C8—H8B	109.2
O4—N1—O3	124.25 (15)	N3^ii—C8—H8B	109.2
O4—N1—C4	118.26 (14)	H8A—C8—H8B	107.9
O3—N1—C4	117.49 (14)	N4—C9—N3	112.19 (12)
O6—N2—O5	124.53 (13)	N4—C9—H9A	109.2
O6—N2—C6	117.87 (13)	N3—C9—H9A	109.2
O5—N2—C6	117.59 (13)	N4—C9—H9B	109.2
C8—N3—C10^ii	107.78 (11)	N3—C9—H9B	109.2
C8—N3—C9	107.86 (11)	H9A—C9—H9B	107.9
C10^ii—N3—C9	107.15 (12)	N4—C10—N3^ii	112.37 (12)
C8—N3—Cu1	113.75 (10)	N4—C10—H10A	109.1
C10^ii—N3—Cu1	110.58 (9)	N3^ii—C10—H10A	109.1
C9—N3—Cu1	109.48 (9)	N4—C10—H10B	109.1
C9—N4—C10	108.29 (12)	N3^ii—C10—H10B	109.1
C9—N4—C11	108.86 (11)	H10A—C10—H10B	107.9
C10—N4—C11	108.74 (11)	N4—C11—N4^ii	111.69 (18)
O2—C1—O1	126.97 (15)	N4—C11—H11A	109.3
O2—C1—C2	118.92 (15)	N4^ii—C11—H11A	109.3
O1—C1—C2	114.09 (14)	N4—C11—H11B	109.3
C3—C2—C7	119.87 (15)	N4^ii—C11—H11B	109.3
C3—C2—C1	119.41 (14)	H11A—C11—H11B	107.9
N3^i—Cu1—O1—C1	107.15 (13)	O3—N1—C4—C3	12.1 (2)
N3—Cu1—O1—C1	−72.85 (13)	O4—N1—C4—C5	13.6 (2)
O1W^i—Cu1—O1—C1	22.56 (14)	O3—N1—C4—C5	−166.01 (15)
O1W—Cu1—O1—C1	−157.44 (14)	C3—C4—C5—C6	−1.2 (2)
O1^i—Cu1—N3—C8	−84.85 (8)	N1—C4—C5—C6	176.82 (14)
O1—Cu1—N3—C8	95.15 (8)	C4—C5—C6—C7	1.6 (2)
O1W^i—Cu1—N3—C8	0.22 (8)	C4—C5—C6—N2	−176.08 (13)
O1W—Cu1—N3—C8	−179.78 (8)	O6—N2—C6—C7	18.2 (2)
O1^i—Cu1—N3—C10^ii	153.71 (10)	O5—N2—C6—C7	−160.69 (14)
O1—Cu1—N3—C10^ii	−26.29 (10)	O6—N2—C6—C5	−163.99 (14)
O1W^i—Cu1—N3—C10^ii	−121.22 (10)	O5—N2—C6—C5	17.1 (2)
O1W—Cu1—N3—C10^ii	58.78 (10)	C5—C6—C7—C2	−0.8 (2)
O1^i—Cu1—N3—C9	35.88 (10)	N2—C6—C7—C2	176.82 (13)
O1—Cu1—N3—C9	−144.12 (10)	C3—C2—C7—C6	−0.4 (2)
O1W^i—Cu1—N3—C9	120.95 (10)	C1—C2—C7—C6	−178.40 (14)
O1W—Cu1—N3—C9	−59.05 (10)	C10^ii—N3—C8—N3^ii	−57.71 (9)
Cu1—O1—C1—O2	−6.9 (2)	C9—N3—C8—N3^ii	57.67 (9)
Cu1—O1—C1—C2	171.63 (9)	Cu1—N3—C8—N3^ii	179.31 (10)
O2—C1—C2—C3	1.8 (2)	C10—N4—C9—N3	59.30 (16)
O1—C1—C2—C3	−176.83 (14)	C11—N4—C9—N3	−58.76 (16)
O2—C1—C2—C7	179.81 (14)	C8—N3—C9—N4	−58.51 (16)
O1—C1—C2—C7	1.1 (2)	C10^ii—N3—C9—N4	57.28 (15)
C7—C2—C3—C4	0.8 (2)	Cu1—N3—C9—N4	177.24 (10)
C1—C2—C3—C4	178.80 (14)	C9—N4—C10—N3^ii	−59.50 (16)
C2—C3—C4—C5	0.0 (2)	C11—N4—C10—N3^ii	58.64 (16)
C2—C3—C4—N1	−177.94 (14)	C9—N4—C11—N4^ii	59.00 (9)
O4—N1—C4—C3	−168.30 (15)	C10—N4—C11—N4^ii	−58.78 (9)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O2^i	0.83 (1)	2.14 (2)	2.826 (2)	140 (2)
O1w—H12···O2w	0.83 (1)	1.95 (1)	2.780 (2)	175 (2)
O2w—H21···O2^iii	0.83 (1)	2.06 (2)	2.838 (2)	155 (3)
O2w—H22···N4^iv	0.83 (1)	2.45 (2)	3.173 (2)	146 (2)

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

(Cu2) Diaquabis(3,5-dinitrobenzoato)[1,3,5,7- tetraazatricyclo[3.3.1.1^3,7]decane]copper(II) dihydrate

Crystal data

Cu(H2O)2(C6H12N4)(C7H3N2O6)2·2H2O	F(000) = 1436
Mr = 698.03	Dx = 1.837 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7395 reflections
a = 23.0151 (8) Å	θ = 3.7–27.5°
b = 8.9752 (3) Å	µ = 0.97 mm^−1
c = 12.3404 (5) Å	T = 100 K
β = 98.108 (3)°	Block, blue
V = 2523.61 (16) Å^3	0.59 × 0.46 × 0.38 mm
Z = 4

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	2911 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2641 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.032
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 2.9°
ω scan	h = −29→29
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −11→11
Tmin = 0.658, Tmax = 0.751	l = −14→16
14090 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.040P)^2 + 2.708P] where P = (Fo^2 + 2Fc^2)/3
2911 reflections	(Δ/σ)max = 0.001
222 parameters	Δρmax = 0.32 e Å^−3
4 restraints	Δρmin = −0.76 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.5000	0.5000	0.5000	0.00535 (9)
O1	0.58522 (5)	0.51224 (12)	0.53207 (9)	0.0080 (2)
O2	0.61859 (5)	0.34881 (13)	0.41709 (9)	0.0130 (2)
O3	0.82855 (5)	0.37428 (15)	0.37999 (10)	0.0188 (3)
O4	0.88902 (5)	0.47917 (14)	0.50747 (11)	0.0162 (3)
O5	0.80894 (5)	0.85987 (13)	0.72015 (9)	0.0117 (2)
O6	0.72395 (5)	0.81752 (14)	0.77218 (9)	0.0139 (3)
O1W	0.50065 (5)	0.72996 (13)	0.58502 (9)	0.0107 (2)
O2W	0.59277 (6)	0.84127 (15)	0.73271 (11)	0.0182 (3)
N1	0.83942 (6)	0.44777 (16)	0.46402 (11)	0.0102 (3)
N2	0.76269 (6)	0.78999 (15)	0.71606 (10)	0.0083 (3)
N3	0.50043 (5)	0.62990 (15)	0.35004 (10)	0.0062 (3)
N4	0.44670 (6)	0.82428 (15)	0.23683 (10)	0.0082 (3)
C1	0.62522 (6)	0.44749 (18)	0.48768 (12)	0.0075 (3)
C2	0.68668 (7)	0.50437 (16)	0.52671 (13)	0.0075 (3)
C3	0.73371 (7)	0.44780 (18)	0.47990 (12)	0.0078 (3)
H3	0.7277	0.3729	0.4250	0.009*
C4	0.78940 (7)	0.50297 (17)	0.51504 (13)	0.0083 (3)
C5	0.80073 (6)	0.61217 (17)	0.59404 (12)	0.0081 (3)
H5	0.8394	0.6474	0.6177	0.010*
C6	0.75260 (7)	0.66718 (17)	0.63665 (12)	0.0077 (3)
C7	0.69594 (6)	0.61592 (17)	0.60588 (12)	0.0075 (3)
H7	0.6641	0.6558	0.6380	0.009*
C8	0.5000	0.5370 (2)	0.2500	0.0064 (4)
H8A	0.4649	0.4722	0.2413	0.008*	0.50
H8B	0.5351	0.4722	0.2587	0.008*	0.50
C9	0.44744 (6)	0.72903 (17)	0.33350 (12)	0.0077 (3)
H9A	0.4116	0.6668	0.3251	0.009*
H9B	0.4471	0.7924	0.3991	0.009*
C10	0.44668 (6)	0.72883 (17)	0.14076 (12)	0.0079 (3)
H10A	0.4456	0.7921	0.0748	0.009*
H10B	0.4109	0.6664	0.1317	0.009*
C11	0.5000	0.9162 (2)	0.2500	0.0103 (4)
H11A	0.5003	0.9810	0.3150	0.012*	0.50
H11B	0.4997	0.9810	0.1850	0.012*	0.50
H11	0.4675 (6)	0.745 (3)	0.6029 (19)	0.033 (7)*
H12	0.5269 (7)	0.761 (2)	0.6330 (14)	0.023 (6)*
H21	0.6099 (11)	0.793 (3)	0.7855 (16)	0.049 (8)*
H22	0.5968 (13)	0.9331 (12)	0.741 (2)	0.054 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.00275 (14)	0.00738 (15)	0.00582 (15)	−0.00027 (9)	0.00023 (9)	0.00011 (9)
O1	0.0052 (5)	0.0102 (6)	0.0086 (5)	0.0003 (4)	0.0008 (4)	0.0011 (4)
O2	0.0084 (5)	0.0160 (6)	0.0145 (6)	−0.0027 (4)	0.0012 (4)	−0.0059 (5)
O3	0.0119 (6)	0.0284 (7)	0.0164 (6)	0.0004 (5)	0.0024 (5)	−0.0134 (5)
O4	0.0047 (5)	0.0183 (7)	0.0252 (7)	−0.0013 (4)	0.0010 (5)	−0.0088 (5)
O5	0.0104 (5)	0.0114 (6)	0.0129 (6)	−0.0040 (4)	−0.0003 (4)	−0.0013 (4)
O6	0.0103 (5)	0.0189 (6)	0.0130 (6)	0.0016 (5)	0.0033 (4)	−0.0056 (5)
O1W	0.0083 (5)	0.0127 (6)	0.0111 (6)	−0.0007 (4)	0.0012 (4)	−0.0030 (4)
O2W	0.0163 (6)	0.0179 (7)	0.0180 (7)	0.0030 (5)	−0.0054 (5)	−0.0006 (5)
N1	0.0076 (6)	0.0105 (7)	0.0126 (7)	0.0009 (5)	0.0020 (5)	−0.0021 (5)
N2	0.0084 (6)	0.0085 (7)	0.0072 (6)	0.0004 (5)	−0.0017 (5)	0.0000 (5)
N3	0.0046 (6)	0.0080 (6)	0.0060 (6)	−0.0005 (5)	0.0004 (4)	−0.0003 (5)
N4	0.0090 (6)	0.0079 (7)	0.0080 (6)	0.0010 (5)	0.0016 (5)	0.0006 (5)
C1	0.0062 (7)	0.0087 (7)	0.0077 (7)	0.0003 (6)	0.0011 (5)	0.0033 (6)
C2	0.0068 (7)	0.0078 (8)	0.0075 (7)	−0.0006 (5)	−0.0003 (6)	0.0030 (5)
C3	0.0080 (7)	0.0078 (7)	0.0073 (7)	0.0010 (6)	−0.0001 (5)	0.0020 (6)
C4	0.0058 (7)	0.0097 (8)	0.0098 (8)	0.0015 (5)	0.0030 (6)	0.0012 (5)
C5	0.0062 (7)	0.0088 (7)	0.0088 (7)	−0.0006 (6)	−0.0002 (5)	0.0019 (6)
C6	0.0103 (7)	0.0067 (7)	0.0057 (7)	0.0008 (6)	0.0002 (5)	0.0003 (5)
C7	0.0069 (7)	0.0084 (7)	0.0072 (7)	0.0014 (6)	0.0012 (5)	0.0019 (5)
C8	0.0071 (10)	0.0051 (10)	0.0069 (10)	0.000	0.0008 (7)	0.000
C9	0.0065 (7)	0.0091 (8)	0.0076 (7)	0.0017 (6)	0.0013 (5)	0.0008 (6)
C10	0.0057 (7)	0.0092 (7)	0.0085 (7)	0.0013 (6)	0.0002 (5)	−0.0007 (6)
C11	0.0111 (10)	0.0077 (11)	0.0124 (11)	0.000	0.0030 (8)	0.000

Geometric parameters (Å, º)

Cu1—O1	1.9486 (11)	N4—C11	1.4680 (18)
Cu1—O1^i	1.9486 (11)	C1—C2	1.517 (2)
Cu1—N3^i	2.1884 (13)	C2—C7	1.394 (2)
Cu1—N3	2.1884 (13)	C2—C3	1.393 (2)
Cu1—O1W	2.3144 (12)	C3—C4	1.385 (2)
Cu1—O1W^i	2.3144 (12)	C3—H3	0.9500
O1—C1	1.2757 (19)	C4—C5	1.381 (2)
O2—C1	1.2365 (19)	C5—C6	1.383 (2)
O3—N1	1.2247 (18)	C5—H5	0.9500
O4—N1	1.2235 (18)	C6—C7	1.384 (2)
O5—N2	1.2304 (17)	C7—H7	0.9500
O6—N2	1.2287 (17)	C8—N3^ii	1.4884 (17)
O1W—H11	0.834 (10)	C8—H8A	0.9900
O1W—H12	0.832 (10)	C8—H8B	0.9900
O2W—H21	0.832 (10)	C9—H9A	0.9900
O2W—H22	0.834 (10)	C9—H9B	0.9900
N1—C4	1.474 (2)	C10—N3^ii	1.4979 (19)
N2—C6	1.4713 (19)	C10—H10A	0.9900
N3—C8	1.4884 (17)	C10—H10B	0.9900
N3—C10^ii	1.4979 (19)	C11—N4^ii	1.4680 (18)
N3—C9	1.5002 (19)	C11—H11A	0.9900
N4—C10	1.4626 (19)	C11—H11B	0.9900
N4—C9	1.4658 (19)
O1—Cu1—O1^i	180.000 (14)	C3—C2—C1	119.35 (14)
O1—Cu1—N3^i	89.01 (5)	C4—C3—C2	118.60 (15)
O1^i—Cu1—N3^i	90.99 (5)	C4—C3—H3	120.7
O1—Cu1—N3	90.99 (5)	C2—C3—H3	120.7
O1^i—Cu1—N3	89.01 (5)	C5—C4—C3	123.29 (15)
N3^i—Cu1—N3	180.000 (1)	C5—C4—N1	117.32 (14)
O1—Cu1—O1W	85.16 (4)	C3—C4—N1	119.35 (14)
O1^i—Cu1—O1W	94.84 (4)	C6—C5—C4	116.12 (14)
N3^i—Cu1—O1W	95.29 (4)	C6—C5—H5	121.9
N3—Cu1—O1W	84.71 (4)	C4—C5—H5	121.9
O1—Cu1—O1W^i	94.84 (4)	C5—C6—C7	123.45 (14)
O1^i—Cu1—O1W^i	85.16 (4)	C5—C6—N2	117.46 (13)
N3^i—Cu1—O1W^i	84.71 (4)	C7—C6—N2	119.06 (13)
N3—Cu1—O1W^i	95.29 (4)	C6—C7—C2	118.42 (14)
O1W—Cu1—O1W^i	180.0	C6—C7—H7	120.8
C1—O1—Cu1	130.82 (10)	C2—C7—H7	120.8
Cu1—O1W—H11	108.7 (17)	N3—C8—N3^ii	111.90 (17)
Cu1—O1W—H12	125.5 (16)	N3—C8—H8A	109.2
H11—O1W—H12	111 (2)	N3^ii—C8—H8A	109.2
H21—O2W—H22	112 (3)	N3—C8—H8B	109.2
O4—N1—O3	124.18 (14)	N3^ii—C8—H8B	109.2
O4—N1—C4	118.17 (13)	H8A—C8—H8B	107.9
O3—N1—C4	117.65 (13)	N4—C9—N3	111.87 (11)
O6—N2—O5	124.52 (13)	N4—C9—H9A	109.2
O6—N2—C6	117.85 (13)	N3—C9—H9A	109.2
O5—N2—C6	117.62 (12)	N4—C9—H9B	109.2
C8—N3—C10^ii	107.76 (10)	N3—C9—H9B	109.2
C8—N3—C9	108.01 (10)	H9A—C9—H9B	107.9
C10^ii—N3—C9	107.16 (12)	N4—C10—N3^ii	112.24 (12)
C8—N3—Cu1	113.75 (10)	N4—C10—H10A	109.2
C10^ii—N3—Cu1	110.62 (9)	N3^ii—C10—H10A	109.2
C9—N3—Cu1	109.29 (8)	N4—C10—H10B	109.2
C10—N4—C9	108.47 (12)	N3^ii—C10—H10B	109.2
C10—N4—C11	108.87 (11)	H10A—C10—H10B	107.9
C9—N4—C11	108.90 (11)	N4—C11—N4^ii	111.65 (18)
O2—C1—O1	127.16 (14)	N4—C11—H11A	109.3
O2—C1—C2	118.79 (14)	N4^ii—C11—H11A	109.3
O1—C1—C2	114.04 (14)	N4—C11—H11B	109.3
C7—C2—C3	120.11 (14)	N4^ii—C11—H11B	109.3
C7—C2—C1	120.51 (14)	H11A—C11—H11B	108.0
N3^i—Cu1—O1—C1	107.01 (13)	O3—N1—C4—C5	−165.71 (15)
N3—Cu1—O1—C1	−72.99 (13)	O4—N1—C4—C3	−168.44 (15)
O1W—Cu1—O1—C1	−157.60 (13)	O3—N1—C4—C3	12.2 (2)
O1W^i—Cu1—O1—C1	22.40 (13)	C3—C4—C5—C6	−0.9 (2)
O1—Cu1—N3—C8	95.13 (7)	N1—C4—C5—C6	176.91 (14)
O1^i—Cu1—N3—C8	−84.87 (7)	C4—C5—C6—C7	1.6 (2)
O1W—Cu1—N3—C8	−179.82 (7)	C4—C5—C6—N2	−176.36 (13)
O1W^i—Cu1—N3—C8	0.18 (7)	O6—N2—C6—C5	−164.14 (14)
O1—Cu1—N3—C10^ii	−26.32 (10)	O5—N2—C6—C5	17.2 (2)
O1^i—Cu1—N3—C10^ii	153.68 (10)	O6—N2—C6—C7	17.8 (2)
O1W—Cu1—N3—C10^ii	58.73 (9)	O5—N2—C6—C7	−160.81 (14)
O1W^i—Cu1—N3—C10^ii	−121.27 (9)	C5—C6—C7—C2	−0.9 (2)
O1—Cu1—N3—C9	−144.08 (9)	N2—C6—C7—C2	176.99 (13)
O1^i—Cu1—N3—C9	35.92 (9)	C3—C2—C7—C6	−0.5 (2)
O1W—Cu1—N3—C9	−59.03 (9)	C1—C2—C7—C6	−178.19 (13)
O1W^i—Cu1—N3—C9	120.97 (9)	C10^ii—N3—C8—N3^ii	−57.67 (9)
Cu1—O1—C1—O2	−6.7 (2)	C9—N3—C8—N3^ii	57.79 (8)
Cu1—O1—C1—C2	171.77 (9)	Cu1—N3—C8—N3^ii	179.30 (9)
O2—C1—C2—C7	179.76 (14)	C10—N4—C9—N3	59.42 (15)
O1—C1—C2—C7	1.1 (2)	C11—N4—C9—N3	−58.92 (16)
O2—C1—C2—C3	2.0 (2)	C8—N3—C9—N4	−58.47 (15)
O1—C1—C2—C3	−176.62 (13)	C10^ii—N3—C9—N4	57.39 (15)
C7—C2—C3—C4	1.0 (2)	Cu1—N3—C9—N4	177.30 (9)
C1—C2—C3—C4	178.80 (14)	C9—N4—C10—N3^ii	−59.67 (15)
C2—C3—C4—C5	−0.3 (2)	C11—N4—C10—N3^ii	58.69 (16)
C2—C3—C4—N1	−178.12 (13)	C10—N4—C11—N4^ii	−58.93 (9)
O4—N1—C4—C5	13.6 (2)	C9—N4—C11—N4^ii	59.16 (9)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O2^i	0.83 (1)	2.14 (2)	2.831 (2)	140 (2)
O1w—H12···O2w	0.83 (1)	1.95 (1)	2.779 (2)	174 (2)
O2w—H21···O2^iii	0.83 (1)	2.05 (1)	2.839 (2)	157 (3)
O2w—H22···N4^iv	0.83 (1)	2.43 (2)	3.174 (2)	149 (3)

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

(Cu3) Diaquabis(3,5-dinitrobenzoato)[1,3,5,7- tetraazatricyclo[3.3.1.1^3,7]decane]copper(II) dihydrate

Crystal data

Cu(H2O)2(C6H12N4)(C7H3N2O6)2·2H2O	F(000) = 1436
Mr = 698.03	Dx = 1.837 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4401 reflections
a = 23.0144 (11) Å	θ = 3.5–27.5°
b = 8.9745 (5) Å	µ = 0.97 mm^−1
c = 12.3423 (6) Å	T = 100 K
β = 98.069 (5)°	Block, blue
V = 2524.0 (2) Å^3	0.27 × 0.23 × 0.15 mm
Z = 4

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	2914 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2496 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 2.9°
ω scan	h = −29→29
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −11→10
Tmin = 0.828, Tmax = 0.899	l = −16→16
12138 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0374P)^2 + 4.1601P] where P = (Fo^2 + 2Fc^2)/3
2914 reflections	(Δ/σ)max = 0.001
222 parameters	Δρmax = 0.39 e Å^−3
4 restraints	Δρmin = −0.57 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.5000	0.5000	0.5000	0.00723 (10)
O1	0.58519 (6)	0.51207 (14)	0.53213 (11)	0.0098 (3)
O2	0.61861 (6)	0.34911 (16)	0.41710 (11)	0.0148 (3)
O3	0.82854 (6)	0.37423 (18)	0.37985 (11)	0.0206 (3)
O4	0.88901 (6)	0.47938 (16)	0.50754 (12)	0.0177 (3)
O5	0.80893 (6)	0.85982 (15)	0.72034 (10)	0.0131 (3)
O6	0.72396 (6)	0.81749 (16)	0.77213 (11)	0.0157 (3)
O1W	0.50062 (6)	0.72994 (16)	0.58486 (11)	0.0128 (3)
O2W	0.59276 (7)	0.84125 (18)	0.73270 (12)	0.0202 (3)
N1	0.83935 (7)	0.44779 (19)	0.46407 (13)	0.0119 (3)
N2	0.76271 (7)	0.79037 (18)	0.71585 (12)	0.0105 (3)
N3	0.50044 (6)	0.62971 (17)	0.35006 (12)	0.0080 (3)
N4	0.44664 (7)	0.82435 (18)	0.23691 (12)	0.0097 (3)
C1	0.62528 (8)	0.4473 (2)	0.48766 (14)	0.0089 (4)
C2	0.68671 (8)	0.5043 (2)	0.52655 (15)	0.0092 (4)
C3	0.73359 (8)	0.4479 (2)	0.48009 (14)	0.0100 (4)
H3	0.7276	0.3729	0.4253	0.012*
C4	0.78935 (8)	0.5027 (2)	0.51482 (15)	0.0098 (4)
C5	0.80073 (8)	0.6120 (2)	0.59422 (14)	0.0096 (4)
H5	0.8394	0.6470	0.6181	0.012*
C6	0.75262 (8)	0.6671 (2)	0.63662 (14)	0.0097 (4)
C7	0.69593 (8)	0.6159 (2)	0.60576 (14)	0.0094 (4)
H7	0.6641	0.6558	0.6378	0.011*
C8	0.5000	0.5370 (3)	0.2500	0.0088 (5)
H8A	0.5351	0.4721	0.2587	0.011*	0.50
H8B	0.4649	0.4721	0.2413	0.011*	0.50
C9	0.44742 (8)	0.7290 (2)	0.33332 (14)	0.0094 (4)
H9A	0.4116	0.6667	0.3248	0.011*
H9B	0.4470	0.7923	0.3989	0.011*
C10	0.44667 (8)	0.7289 (2)	0.14068 (14)	0.0095 (4)
H10A	0.4457	0.7922	0.0748	0.011*
H10B	0.4108	0.6666	0.1315	0.011*
C11	0.5000	0.9165 (3)	0.2500	0.0109 (5)
H11A	0.5003	0.9814	0.3150	0.013*	0.50
H11B	0.4997	0.9814	0.1850	0.013*	0.50
H11	0.4674 (7)	0.743 (3)	0.603 (2)	0.039 (8)*
H12	0.5274 (7)	0.758 (2)	0.6335 (13)	0.013 (6)*
H21	0.6107 (11)	0.796 (3)	0.7861 (16)	0.040 (8)*
H22	0.5969 (15)	0.9328 (13)	0.741 (3)	0.060 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.00485 (17)	0.00888 (17)	0.00787 (16)	−0.00036 (11)	0.00066 (12)	0.00002 (11)
O1	0.0063 (6)	0.0117 (7)	0.0114 (6)	−0.0004 (5)	0.0015 (5)	0.0012 (5)
O2	0.0109 (7)	0.0170 (7)	0.0164 (7)	−0.0028 (5)	0.0018 (5)	−0.0063 (5)
O3	0.0137 (7)	0.0286 (9)	0.0194 (7)	0.0005 (6)	0.0020 (6)	−0.0132 (6)
O4	0.0068 (7)	0.0208 (8)	0.0249 (8)	−0.0019 (5)	0.0010 (6)	−0.0085 (6)
O5	0.0116 (7)	0.0129 (7)	0.0142 (6)	−0.0037 (5)	0.0002 (5)	−0.0007 (5)
O6	0.0125 (7)	0.0197 (8)	0.0155 (7)	0.0015 (6)	0.0046 (6)	−0.0060 (6)
O1W	0.0094 (7)	0.0153 (7)	0.0134 (6)	−0.0004 (5)	0.0007 (6)	−0.0024 (5)
O2W	0.0179 (8)	0.0204 (9)	0.0202 (8)	0.0026 (6)	−0.0052 (6)	−0.0003 (6)
N1	0.0086 (8)	0.0125 (8)	0.0147 (8)	0.0001 (6)	0.0021 (6)	−0.0026 (6)
N2	0.0107 (8)	0.0102 (8)	0.0098 (7)	0.0013 (6)	−0.0012 (6)	−0.0001 (6)
N3	0.0058 (7)	0.0094 (8)	0.0088 (7)	−0.0003 (6)	0.0016 (6)	−0.0012 (6)
N4	0.0098 (8)	0.0101 (8)	0.0095 (7)	0.0001 (6)	0.0024 (6)	0.0007 (6)
C1	0.0074 (9)	0.0099 (9)	0.0095 (8)	−0.0004 (7)	0.0012 (7)	0.0041 (7)
C2	0.0083 (9)	0.0102 (9)	0.0086 (8)	0.0001 (7)	−0.0002 (7)	0.0030 (6)
C3	0.0104 (9)	0.0091 (9)	0.0100 (8)	−0.0002 (7)	0.0002 (7)	0.0007 (7)
C4	0.0081 (9)	0.0101 (9)	0.0118 (8)	0.0015 (7)	0.0031 (7)	0.0015 (7)
C5	0.0077 (9)	0.0108 (9)	0.0098 (8)	−0.0009 (7)	−0.0009 (7)	0.0012 (7)
C6	0.0115 (9)	0.0090 (9)	0.0082 (8)	0.0002 (7)	0.0004 (7)	0.0008 (7)
C7	0.0087 (9)	0.0107 (9)	0.0092 (8)	0.0007 (7)	0.0026 (7)	0.0014 (7)
C8	0.0091 (12)	0.0076 (12)	0.0096 (12)	0.000	0.0013 (10)	0.000
C9	0.0081 (9)	0.0103 (9)	0.0104 (8)	0.0024 (7)	0.0030 (7)	0.0005 (7)
C10	0.0072 (8)	0.0112 (9)	0.0099 (8)	0.0021 (7)	0.0000 (7)	−0.0008 (7)
C11	0.0106 (13)	0.0090 (13)	0.0134 (12)	0.000	0.0020 (10)	0.000

Geometric parameters (Å, º)

Cu1—O1^i	1.9480 (13)	N4—C11	1.471 (2)
Cu1—O1	1.9480 (13)	C1—C2	1.516 (3)
Cu1—N3	2.1875 (15)	C2—C3	1.387 (3)
Cu1—N3^i	2.1875 (15)	C2—C7	1.395 (3)
Cu1—O1W^i	2.3133 (14)	C3—C4	1.385 (3)
Cu1—O1W	2.3133 (14)	C3—H3	0.9500
O1—C1	1.277 (2)	C4—C5	1.385 (3)
O2—C1	1.234 (2)	C5—C6	1.381 (3)
O3—N1	1.227 (2)	C5—H5	0.9500
O4—N1	1.226 (2)	C6—C7	1.385 (3)
O5—N2	1.227 (2)	C7—H7	0.9500
O6—N2	1.229 (2)	C8—N3^ii	1.488 (2)
O1W—H11	0.836 (10)	C8—H8A	0.9900
O1W—H12	0.836 (10)	C8—H8B	0.9900
O2W—H21	0.834 (10)	C9—H9A	0.9900
O2W—H22	0.832 (10)	C9—H9B	0.9900
N1—C4	1.471 (2)	C10—N3^ii	1.499 (2)
N2—C6	1.473 (2)	C10—H10A	0.9900
N3—C8	1.488 (2)	C10—H10B	0.9900
N3—C10^ii	1.499 (2)	C11—N4^ii	1.471 (2)
N3—C9	1.502 (2)	C11—H11A	0.9900
N4—C9	1.464 (2)	C11—H11B	0.9900
N4—C10	1.465 (2)
O1^i—Cu1—O1	180.000 (16)	C7—C2—C1	120.46 (17)
O1^i—Cu1—N3	88.94 (5)	C4—C3—C2	118.91 (17)
O1—Cu1—N3	91.06 (5)	C4—C3—H3	120.5
O1^i—Cu1—N3^i	91.06 (5)	C2—C3—H3	120.5
O1—Cu1—N3^i	88.94 (5)	C3—C4—C5	123.06 (18)
N3—Cu1—N3^i	180.0	C3—C4—N1	119.71 (16)
O1^i—Cu1—O1W^i	85.19 (5)	C5—C4—N1	117.20 (17)
O1—Cu1—O1W^i	94.81 (5)	C6—C5—C4	116.07 (17)
N3—Cu1—O1W^i	95.29 (5)	C6—C5—H5	122.0
N3^i—Cu1—O1W^i	84.71 (5)	C4—C5—H5	122.0
O1^i—Cu1—O1W	94.81 (5)	C5—C6—C7	123.46 (17)
O1—Cu1—O1W	85.19 (5)	C5—C6—N2	117.41 (16)
N3—Cu1—O1W	84.71 (5)	C7—C6—N2	119.09 (16)
N3^i—Cu1—O1W	95.29 (5)	C6—C7—C2	118.39 (17)
O1W^i—Cu1—O1W	180.00 (6)	C6—C7—H7	120.8
C1—O1—Cu1	130.86 (12)	C2—C7—H7	120.8
Cu1—O1W—H11	108 (2)	N3^ii—C8—N3	112.0 (2)
Cu1—O1W—H12	123.2 (16)	N3^ii—C8—H8A	109.2
H11—O1W—H12	112 (2)	N3—C8—H8A	109.2
H21—O2W—H22	110 (3)	N3^ii—C8—H8B	109.2
O4—N1—O3	124.13 (16)	N3—C8—H8B	109.2
O4—N1—C4	118.25 (15)	H8A—C8—H8B	107.9
O3—N1—C4	117.61 (15)	N4—C9—N3	112.07 (14)
O5—N2—O6	124.53 (16)	N4—C9—H9A	109.2
O5—N2—C6	117.78 (15)	N3—C9—H9A	109.2
O6—N2—C6	117.68 (15)	N4—C9—H9B	109.2
C8—N3—C10^ii	107.83 (12)	N3—C9—H9B	109.2
C8—N3—C9	107.87 (12)	H9A—C9—H9B	107.9
C10^ii—N3—C9	107.06 (14)	N4—C10—N3^ii	112.23 (14)
C8—N3—Cu1	113.85 (12)	N4—C10—H10A	109.2
C10^ii—N3—Cu1	110.58 (10)	N3^ii—C10—H10A	109.2
C9—N3—Cu1	109.39 (10)	N4—C10—H10B	109.2
C9—N4—C10	108.42 (14)	N3^ii—C10—H10B	109.2
C9—N4—C11	108.95 (13)	H10A—C10—H10B	107.9
C10—N4—C11	108.82 (13)	N4—C11—N4^ii	111.6 (2)
O2—C1—O1	127.05 (17)	N4—C11—H11A	109.3
O2—C1—C2	118.84 (16)	N4^ii—C11—H11A	109.3
O1—C1—C2	114.10 (16)	N4—C11—H11B	109.3
C3—C2—C7	120.08 (17)	N4^ii—C11—H11B	109.3
C3—C2—C1	119.42 (16)	H11A—C11—H11B	108.0
N3—Cu1—O1—C1	−72.85 (15)	O3—N1—C4—C3	12.3 (3)
N3^i—Cu1—O1—C1	107.15 (15)	O4—N1—C4—C5	13.4 (2)
O1W^i—Cu1—O1—C1	22.55 (15)	O3—N1—C4—C5	−165.82 (17)
O1W—Cu1—O1—C1	−157.45 (15)	C3—C4—C5—C6	−1.2 (3)
O1^i—Cu1—N3—C8	−84.86 (9)	N1—C4—C5—C6	176.83 (16)
O1—Cu1—N3—C8	95.14 (9)	C4—C5—C6—C7	1.7 (3)
O1W^i—Cu1—N3—C8	0.22 (9)	C4—C5—C6—N2	−176.04 (16)
O1W—Cu1—N3—C8	−179.78 (9)	O5—N2—C6—C5	16.9 (2)
O1^i—Cu1—N3—C10^ii	153.57 (12)	O6—N2—C6—C5	−163.85 (16)
O1—Cu1—N3—C10^ii	−26.43 (12)	O5—N2—C6—C7	−161.02 (16)
O1W^i—Cu1—N3—C10^ii	−121.36 (11)	O6—N2—C6—C7	18.3 (2)
O1W—Cu1—N3—C10^ii	58.64 (11)	C5—C6—C7—C2	−0.9 (3)
O1^i—Cu1—N3—C9	35.89 (11)	N2—C6—C7—C2	176.81 (16)
O1—Cu1—N3—C9	−144.11 (11)	C3—C2—C7—C6	−0.5 (3)
O1W^i—Cu1—N3—C9	120.97 (11)	C1—C2—C7—C6	−178.32 (16)
O1W—Cu1—N3—C9	−59.03 (11)	C10^ii—N3—C8—N3^ii	−57.63 (10)
Cu1—O1—C1—O2	−6.7 (3)	C9—N3—C8—N3^ii	57.68 (10)
Cu1—O1—C1—C2	171.61 (11)	Cu1—N3—C8—N3^ii	179.28 (11)
O2—C1—C2—C3	1.7 (3)	C10—N4—C9—N3	59.42 (18)
O1—C1—C2—C3	−176.73 (16)	C11—N4—C9—N3	−58.86 (19)
O2—C1—C2—C7	179.62 (17)	C8—N3—C9—N4	−58.48 (18)
O1—C1—C2—C7	1.2 (2)	C10^ii—N3—C9—N4	57.33 (18)
C7—C2—C3—C4	0.9 (3)	Cu1—N3—C9—N4	177.19 (11)
C1—C2—C3—C4	178.82 (16)	C9—N4—C10—N3^ii	−59.49 (18)
C2—C3—C4—C5	−0.1 (3)	C11—N4—C10—N3^ii	58.87 (19)
C2—C3—C4—N1	−178.07 (16)	C9—N4—C11—N4^ii	59.07 (11)
O4—N1—C4—C3	−168.45 (17)	C10—N4—C11—N4^ii	−58.96 (11)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O2^i	0.84 (1)	2.13 (2)	2.831 (2)	142 (3)
O1w—H12···O2w	0.84 (1)	1.95 (1)	2.782 (2)	172 (2)
O2w—H21···O2^iii	0.83 (1)	2.06 (2)	2.841 (2)	155 (3)
O2w—H22···N4^iv	0.83 (1)	2.43 (2)	3.173 (2)	149 (3)

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

(Cu4) Diaquabis(3,5-dinitrobenzoato)[1,3,5,7- tetraazatricyclo[3.3.1.1^3,7]decane]copper(II) dihydrate

Crystal data

Cu(H2O)2(C6H12N4)(C7H3N2O6)2·2H2O	F(000) = 1436
Mr = 698.03	Dx = 1.838 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4308 reflections
a = 23.0253 (12) Å	θ = 3.6–27.4°
b = 8.9728 (5) Å	µ = 0.97 mm^−1
c = 12.3325 (7) Å	T = 100 K
β = 98.120 (5)°	Block, blue
V = 2522.4 (2) Å^3	0.19 × 0.16 × 0.07 mm
Z = 4

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	2914 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2414 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.048
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 2.9°
ω scan	h = −30→29
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −11→11
Tmin = 0.879, Tmax = 0.946	l = −15→16
14984 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0341P)^2 + 3.9381P] where P = (Fo^2 + 2Fc^2)/3
2914 reflections	(Δ/σ)max = 0.001
222 parameters	Δρmax = 0.41 e Å^−3
4 restraints	Δρmin = −0.38 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.5000	0.5000	0.5000	0.00698 (11)
O1	0.58508 (6)	0.51214 (14)	0.53194 (11)	0.0091 (3)
O2	0.61853 (6)	0.34894 (16)	0.41709 (12)	0.0142 (3)
O3	0.82856 (7)	0.37397 (18)	0.37982 (13)	0.0200 (4)
O4	0.88899 (6)	0.47963 (16)	0.50742 (13)	0.0170 (3)
O5	0.80883 (6)	0.85972 (16)	0.72016 (12)	0.0130 (3)
O6	0.72399 (6)	0.81773 (16)	0.77215 (12)	0.0156 (3)
O1W	0.50072 (7)	0.72999 (16)	0.58515 (12)	0.0124 (3)
O2W	0.59278 (7)	0.84123 (18)	0.73270 (14)	0.0202 (4)
N1	0.83943 (7)	0.44777 (19)	0.46435 (14)	0.0115 (4)
N2	0.76267 (7)	0.79004 (18)	0.71602 (14)	0.0105 (4)
N3	0.50052 (7)	0.62983 (18)	0.35017 (13)	0.0081 (3)
N4	0.44664 (7)	0.82427 (18)	0.23684 (14)	0.0099 (4)
C1	0.62539 (9)	0.4475 (2)	0.48761 (16)	0.0097 (4)
C2	0.68672 (9)	0.5044 (2)	0.52674 (16)	0.0087 (4)
C3	0.73364 (9)	0.4479 (2)	0.48018 (16)	0.0094 (4)
H3	0.7276	0.3729	0.4254	0.011*
C4	0.78927 (9)	0.5026 (2)	0.51487 (17)	0.0096 (4)
C5	0.80064 (9)	0.6122 (2)	0.59412 (16)	0.0096 (4)
H5	0.8392	0.6476	0.6177	0.011*
C6	0.75270 (9)	0.6671 (2)	0.63690 (16)	0.0090 (4)
C7	0.69593 (9)	0.6160 (2)	0.60591 (16)	0.0093 (4)
H7	0.6641	0.6561	0.6378	0.011*
C8	0.5000	0.5369 (3)	0.2500	0.0084 (5)
H8A	0.5351	0.4720	0.2586	0.010*	0.50
H8B	0.4649	0.4720	0.2414	0.010*	0.50
C9	0.44745 (8)	0.7291 (2)	0.33365 (16)	0.0092 (4)
H9A	0.4116	0.6668	0.3253	0.011*
H9B	0.4472	0.7925	0.3992	0.011*
C10	0.44660 (9)	0.7285 (2)	0.14074 (16)	0.0094 (4)
H10A	0.4454	0.7915	0.0746	0.011*
H10B	0.4108	0.6659	0.1319	0.011*
C11	0.5000	0.9163 (3)	0.2500	0.0107 (6)
H11A	0.5003	0.9812	0.3150	0.013*	0.50
H11B	0.4997	0.9812	0.1850	0.013*	0.50
H11	0.4671 (7)	0.740 (3)	0.602 (2)	0.035 (8)*
H12	0.5273 (10)	0.759 (3)	0.6342 (18)	0.039 (9)*
H21	0.6111 (12)	0.794 (3)	0.7848 (18)	0.042 (9)*
H22	0.5977 (14)	0.9325 (13)	0.743 (3)	0.051 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.00518 (18)	0.00857 (18)	0.00723 (18)	−0.00029 (12)	0.00103 (13)	0.00014 (12)
O1	0.0058 (7)	0.0112 (7)	0.0104 (7)	0.0001 (5)	0.0010 (5)	0.0015 (5)
O2	0.0097 (7)	0.0171 (8)	0.0157 (8)	−0.0025 (6)	0.0013 (6)	−0.0065 (6)
O3	0.0134 (8)	0.0286 (9)	0.0179 (8)	0.0004 (7)	0.0019 (6)	−0.0129 (7)
O4	0.0061 (7)	0.0202 (8)	0.0243 (9)	−0.0025 (6)	−0.0001 (6)	−0.0090 (6)
O5	0.0113 (7)	0.0127 (7)	0.0146 (8)	−0.0041 (6)	0.0000 (6)	0.0000 (6)
O6	0.0127 (8)	0.0191 (8)	0.0156 (8)	0.0025 (6)	0.0046 (6)	−0.0062 (6)
O1W	0.0096 (8)	0.0143 (7)	0.0132 (8)	−0.0004 (6)	0.0015 (6)	−0.0025 (6)
O2W	0.0180 (9)	0.0195 (9)	0.0209 (9)	0.0023 (7)	−0.0049 (7)	−0.0003 (7)
N1	0.0089 (9)	0.0129 (8)	0.0131 (9)	0.0017 (7)	0.0023 (7)	−0.0013 (7)
N2	0.0117 (9)	0.0089 (8)	0.0103 (9)	0.0010 (7)	−0.0005 (7)	−0.0016 (7)
N3	0.0055 (8)	0.0093 (8)	0.0096 (8)	−0.0010 (6)	0.0010 (6)	−0.0013 (6)
N4	0.0121 (9)	0.0087 (8)	0.0090 (8)	0.0014 (6)	0.0020 (7)	0.0004 (6)
C1	0.0094 (10)	0.0105 (9)	0.0088 (10)	−0.0002 (8)	0.0002 (8)	0.0037 (7)
C2	0.0086 (10)	0.0088 (9)	0.0081 (9)	−0.0015 (7)	−0.0006 (8)	0.0030 (7)
C3	0.0104 (10)	0.0093 (9)	0.0082 (10)	0.0002 (8)	0.0006 (8)	0.0018 (7)
C4	0.0087 (10)	0.0096 (9)	0.0109 (10)	0.0009 (7)	0.0031 (8)	0.0011 (7)
C5	0.0074 (10)	0.0109 (9)	0.0100 (10)	−0.0004 (7)	0.0000 (8)	0.0019 (8)
C6	0.0110 (10)	0.0073 (9)	0.0083 (9)	−0.0005 (7)	−0.0004 (8)	0.0006 (7)
C7	0.0086 (10)	0.0104 (9)	0.0090 (9)	0.0016 (7)	0.0011 (8)	0.0030 (7)
C8	0.0089 (14)	0.0079 (13)	0.0085 (13)	0.000	0.0009 (11)	0.000
C9	0.0066 (10)	0.0107 (10)	0.0107 (10)	0.0014 (7)	0.0025 (8)	0.0007 (7)
C10	0.0084 (10)	0.0110 (9)	0.0087 (10)	0.0031 (7)	0.0007 (8)	−0.0012 (7)
C11	0.0135 (15)	0.0065 (13)	0.0127 (14)	0.000	0.0042 (11)	0.000

Geometric parameters (Å, º)

Cu1—O1^i	1.9460 (14)	N4—C11	1.470 (2)
Cu1—O1	1.9460 (14)	C1—C2	1.515 (3)
Cu1—N3	2.1858 (16)	C2—C3	1.389 (3)
Cu1—N3^i	2.1858 (16)	C2—C7	1.394 (3)
Cu1—O1W	2.3144 (14)	C3—C4	1.382 (3)
Cu1—O1W^i	2.3144 (14)	C3—H3	0.9500
O1—C1	1.281 (2)	C4—C5	1.385 (3)
O2—C1	1.235 (2)	C5—C6	1.380 (3)
O3—N1	1.231 (2)	C5—H5	0.9500
O4—N1	1.223 (2)	C6—C7	1.387 (3)
O5—N2	1.228 (2)	C7—H7	0.9500
O6—N2	1.228 (2)	C8—N3^ii	1.489 (2)
O1W—H11	0.837 (10)	C8—H8A	0.9900
O1W—H12	0.839 (10)	C8—H8B	0.9900
O2W—H21	0.832 (10)	C9—H9A	0.9900
O2W—H22	0.834 (10)	C9—H9B	0.9900
N1—C4	1.472 (3)	C10—N3^ii	1.497 (2)
N2—C6	1.469 (2)	C10—H10A	0.9900
N3—C8	1.489 (2)	C10—H10B	0.9900
N3—C10^ii	1.497 (2)	C11—N4^ii	1.470 (2)
N3—C9	1.502 (2)	C11—H11A	0.9900
N4—C10	1.464 (2)	C11—H11B	0.9900
N4—C9	1.466 (2)
O1^i—Cu1—O1	180.00 (9)	C7—C2—C1	120.54 (18)
O1^i—Cu1—N3	89.10 (6)	C4—C3—C2	118.92 (18)
O1—Cu1—N3	90.90 (6)	C4—C3—H3	120.5
O1^i—Cu1—N3^i	90.90 (6)	C2—C3—H3	120.5
O1—Cu1—N3^i	89.10 (6)	C3—C4—C5	123.03 (19)
N3—Cu1—N3^i	180.0	C3—C4—N1	119.90 (17)
O1^i—Cu1—O1W	94.83 (5)	C5—C4—N1	117.03 (18)
O1—Cu1—O1W	85.17 (5)	C6—C5—C4	116.20 (19)
N3—Cu1—O1W	84.71 (6)	C6—C5—H5	121.9
N3^i—Cu1—O1W	95.29 (6)	C4—C5—H5	121.9
O1^i—Cu1—O1W^i	85.17 (5)	C5—C6—C7	123.39 (18)
O1—Cu1—O1W^i	94.83 (5)	C5—C6—N2	117.61 (18)
N3—Cu1—O1W^i	95.29 (6)	C7—C6—N2	118.95 (17)
N3^i—Cu1—O1W^i	84.71 (6)	C6—C7—C2	118.35 (18)
O1W—Cu1—O1W^i	180.000 (1)	C6—C7—H7	120.8
C1—O1—Cu1	131.13 (13)	C2—C7—H7	120.8
Cu1—O1W—H11	106 (2)	N3^ii—C8—N3	111.9 (2)
Cu1—O1W—H12	124 (2)	N3^ii—C8—H8A	109.2
H11—O1W—H12	113 (3)	N3—C8—H8A	109.2
H21—O2W—H22	110 (3)	N3^ii—C8—H8B	109.2
O4—N1—O3	124.03 (17)	N3—C8—H8B	109.2
O4—N1—C4	118.55 (16)	H8A—C8—H8B	107.9
O3—N1—C4	117.42 (17)	N4—C9—N3	111.86 (15)
O6—N2—O5	124.46 (16)	N4—C9—H9A	109.2
O6—N2—C6	117.94 (16)	N3—C9—H9A	109.2
O5—N2—C6	117.59 (16)	N4—C9—H9B	109.2
C8—N3—C10^ii	107.72 (13)	N3—C9—H9B	109.2
C8—N3—C9	107.96 (14)	H9A—C9—H9B	107.9
C10^ii—N3—C9	107.28 (15)	N4—C10—N3^ii	112.28 (16)
C8—N3—Cu1	113.74 (12)	N4—C10—H10A	109.1
C10^ii—N3—Cu1	110.69 (12)	N3^ii—C10—H10A	109.1
C9—N3—Cu1	109.21 (11)	N4—C10—H10B	109.1
C10—N4—C9	108.40 (15)	N3^ii—C10—H10B	109.1
C10—N4—C11	108.90 (14)	H10A—C10—H10B	107.9
C9—N4—C11	108.84 (14)	N4—C11—N4^ii	111.7 (2)
O2—C1—O1	126.64 (19)	N4—C11—H11A	109.3
O2—C1—C2	119.12 (18)	N4^ii—C11—H11A	109.3
O1—C1—C2	114.22 (17)	N4—C11—H11B	109.3
C3—C2—C7	120.10 (18)	N4^ii—C11—H11B	109.3
C3—C2—C1	119.32 (17)	H11A—C11—H11B	107.9
N3—Cu1—O1—C1	−72.97 (17)	O3—N1—C4—C3	12.4 (3)
N3^i—Cu1—O1—C1	107.03 (17)	O4—N1—C4—C5	13.3 (3)
O1W—Cu1—O1—C1	−157.58 (17)	O3—N1—C4—C5	−165.67 (18)
O1W^i—Cu1—O1—C1	22.42 (17)	C3—C4—C5—C6	−0.8 (3)
O1^i—Cu1—N3—C8	−84.81 (9)	N1—C4—C5—C6	177.11 (17)
O1—Cu1—N3—C8	95.19 (9)	C4—C5—C6—C7	1.3 (3)
O1W—Cu1—N3—C8	−179.74 (10)	C4—C5—C6—N2	−176.23 (17)
O1W^i—Cu1—N3—C8	0.26 (10)	O6—N2—C6—C5	−164.29 (18)
O1^i—Cu1—N3—C10^ii	153.76 (12)	O5—N2—C6—C5	16.9 (3)
O1—Cu1—N3—C10^ii	−26.24 (12)	O6—N2—C6—C7	18.1 (3)
O1W—Cu1—N3—C10^ii	58.82 (12)	O5—N2—C6—C7	−160.73 (17)
O1W^i—Cu1—N3—C10^ii	−121.18 (12)	C5—C6—C7—C2	−0.6 (3)
O1^i—Cu1—N3—C9	35.85 (12)	N2—C6—C7—C2	176.88 (17)
O1—Cu1—N3—C9	−144.15 (12)	C3—C2—C7—C6	−0.6 (3)
O1W—Cu1—N3—C9	−59.08 (12)	C1—C2—C7—C6	−178.32 (17)
O1W^i—Cu1—N3—C9	120.92 (12)	C10^ii—N3—C8—N3^ii	−57.77 (11)
Cu1—O1—C1—O2	−6.7 (3)	C9—N3—C8—N3^ii	57.79 (11)
Cu1—O1—C1—C2	171.76 (12)	Cu1—N3—C8—N3^ii	179.15 (11)
O2—C1—C2—C3	1.9 (3)	C10—N4—C9—N3	59.4 (2)
O1—C1—C2—C3	−176.68 (17)	C11—N4—C9—N3	−58.92 (19)
O2—C1—C2—C7	179.72 (18)	C8—N3—C9—N4	−58.45 (19)
O1—C1—C2—C7	1.1 (3)	C10^ii—N3—C9—N4	57.4 (2)
C7—C2—C3—C4	1.0 (3)	Cu1—N3—C9—N4	177.42 (12)
C1—C2—C3—C4	178.75 (17)	C9—N4—C10—N3^ii	−59.8 (2)
C2—C3—C4—C5	−0.2 (3)	C11—N4—C10—N3^ii	58.5 (2)
C2—C3—C4—N1	−178.14 (17)	C10—N4—C11—N4^ii	−58.82 (11)
O4—N1—C4—C3	−168.69 (18)	C9—N4—C11—N4^ii	59.17 (11)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O2^i	0.84 (1)	2.11 (2)	2.832 (2)	144 (3)
O1w—H12···O2w	0.84 (1)	1.94 (1)	2.777 (2)	172 (3)
O2w—H21···O2^iii	0.83 (1)	2.07 (2)	2.838 (2)	154 (3)
O2w—H22···N4^iv	0.83 (1)	2.44 (2)	3.173 (2)	148 (3)

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

(Sn1) Aquachlorotriphenyltin(IV)–2,2'-bipyridine (1/1)

Crystal data

Sn2Cl2(H2O)2(C6H5)6(C10H8N2)2	F(000) = 2256
Mr = 1119.28	Dx = 1.528 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8997 reflections
a = 15.5966 (7) Å	θ = 3.3–27.5°
b = 16.1294 (6) Å	µ = 1.18 mm^−1
c = 20.4387 (9) Å	T = 100 K
β = 108.891 (5)°	Prism, colorless
V = 4864.7 (4) Å^3	0.91 × 0.63 × 0.13 mm
Z = 4

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	5635 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4651 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.034
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 2.9°
ω scan	h = −20→20
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −20→14
Tmin = 0.501, Tmax = 0.857	l = −25→26
21428 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0432P)^2 + 6.3326P] where P = (Fo^2 + 2Fc^2)/3
5635 reflections	(Δ/σ)max = 0.001
306 parameters	Δρmax = 2.56 e Å^−3
2 restraints	Δρmin = −0.67 e Å^−3

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

	x	y	z	Uiso*/Ueq
Sn1	0.295824 (10)	0.599048 (9)	0.322549 (8)	0.01143 (6)
Cl1	0.16581 (4)	0.59853 (4)	0.37054 (4)	0.02093 (14)
O1W	0.42783 (11)	0.60072 (10)	0.29327 (9)	0.0137 (3)
H11	0.4608 (19)	0.6427 (13)	0.2993 (17)	0.037 (9)*
H12	0.4628 (19)	0.5602 (14)	0.3000 (17)	0.041 (10)*
N1	0.53950 (13)	0.74000 (13)	0.32057 (10)	0.0151 (4)
N2	0.54060 (13)	0.46323 (13)	0.32082 (10)	0.0145 (4)
C1	0.34159 (14)	0.71493 (14)	0.37081 (12)	0.0126 (5)
C2	0.36770 (16)	0.72335 (15)	0.44237 (12)	0.0176 (5)
H2	0.3689	0.6758	0.4701	0.021*
C3	0.39209 (17)	0.79989 (17)	0.47415 (13)	0.0222 (5)
H3	0.4096	0.8047	0.5230	0.027*
C4	0.39056 (17)	0.86923 (17)	0.43370 (15)	0.0237 (6)
H4	0.4070	0.9218	0.4550	0.028*
C5	0.36523 (17)	0.86232 (16)	0.36241 (14)	0.0206 (5)
H5	0.3648	0.9099	0.3350	0.025*
C6	0.34052 (16)	0.78563 (15)	0.33121 (13)	0.0165 (5)
H6	0.3226	0.7812	0.2823	0.020*
C7	0.34174 (15)	0.48065 (14)	0.36571 (12)	0.0127 (5)
C8	0.39043 (17)	0.47053 (16)	0.43576 (13)	0.0197 (5)
H8	0.4026	0.5174	0.4655	0.024*
C9	0.42109 (19)	0.39349 (16)	0.46231 (15)	0.0235 (6)
H9	0.4553	0.3879	0.5099	0.028*
C10	0.40239 (18)	0.32429 (16)	0.42015 (15)	0.0238 (6)
H10	0.4228	0.2712	0.4388	0.029*
C11	0.35380 (18)	0.33279 (16)	0.35056 (15)	0.0239 (6)
H11A	0.3406	0.2854	0.3214	0.029*
C12	0.32426 (17)	0.41079 (15)	0.32350 (13)	0.0174 (5)
H12A	0.2918	0.4164	0.2756	0.021*
C13	0.21564 (16)	0.59823 (14)	0.21553 (13)	0.0136 (5)
C14	0.25689 (17)	0.59767 (15)	0.16455 (13)	0.0176 (5)
H14	0.3211	0.5991	0.1775	0.021*
C15	0.20542 (18)	0.59505 (16)	0.09465 (14)	0.0210 (6)
H15	0.2347	0.5941	0.0605	0.025*
C16	0.11170 (18)	0.59382 (16)	0.07502 (14)	0.0214 (6)
H16	0.0765	0.5927	0.0274	0.026*
C17	0.06964 (18)	0.59418 (16)	0.12530 (15)	0.0229 (6)
H17	0.0054	0.5929	0.1120	0.028*
C18	0.12094 (17)	0.59632 (15)	0.19502 (14)	0.0181 (5)
H18	0.0914	0.5965	0.2290	0.022*
C19	0.53314 (16)	0.39167 (14)	0.28565 (13)	0.0142 (5)
C20	0.58411 (16)	0.32165 (16)	0.31396 (13)	0.0190 (5)
H20	0.5759	0.2714	0.2885	0.023*
C21	0.64707 (17)	0.32632 (17)	0.37989 (14)	0.0211 (5)
H21	0.6830	0.2796	0.4001	0.025*
C22	0.65642 (17)	0.40064 (16)	0.41556 (14)	0.0190 (5)
H22	0.6999	0.4065	0.4603	0.023*
C23	0.60106 (16)	0.46596 (16)	0.38450 (12)	0.0171 (5)
H23	0.6062	0.5161	0.4099	0.020*
C24	0.53148 (15)	0.81221 (15)	0.28621 (12)	0.0152 (5)
C25	0.57892 (18)	0.88286 (16)	0.31671 (14)	0.0213 (6)
H25	0.5721	0.9331	0.2913	0.026*
C26	0.63623 (19)	0.87931 (18)	0.38447 (15)	0.0248 (6)
H26	0.6694	0.9268	0.4062	0.030*
C27	0.64412 (17)	0.80526 (18)	0.41981 (14)	0.0242 (6)
H27	0.6826	0.8008	0.4664	0.029*
C28	0.59493 (16)	0.73784 (16)	0.38595 (13)	0.0191 (5)
H28	0.6008	0.6870	0.4105	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.01340 (10)	0.00840 (10)	0.01364 (10)	0.00027 (6)	0.00598 (7)	0.00006 (6)
Cl1	0.0222 (3)	0.0158 (3)	0.0318 (3)	−0.0008 (2)	0.0184 (3)	−0.0018 (2)
O1W	0.0113 (8)	0.0089 (9)	0.0218 (9)	0.0004 (7)	0.0064 (7)	0.0007 (7)
N1	0.0154 (10)	0.0133 (10)	0.0180 (10)	−0.0009 (8)	0.0072 (8)	−0.0024 (8)
N2	0.0137 (10)	0.0134 (10)	0.0171 (10)	−0.0005 (8)	0.0058 (8)	0.0013 (8)
C1	0.0099 (10)	0.0110 (12)	0.0174 (11)	0.0008 (8)	0.0052 (9)	−0.0004 (9)
C2	0.0224 (13)	0.0141 (13)	0.0144 (11)	0.0027 (10)	0.0034 (10)	0.0029 (9)
C3	0.0218 (13)	0.0198 (13)	0.0198 (12)	0.0035 (11)	−0.0003 (10)	−0.0059 (11)
C4	0.0193 (13)	0.0131 (13)	0.0346 (15)	−0.0013 (10)	0.0031 (11)	−0.0087 (11)
C5	0.0186 (13)	0.0115 (13)	0.0317 (15)	−0.0001 (10)	0.0082 (11)	0.0041 (11)
C6	0.0183 (12)	0.0141 (13)	0.0183 (12)	0.0010 (9)	0.0076 (10)	0.0011 (10)
C7	0.0128 (11)	0.0104 (12)	0.0176 (11)	−0.0001 (8)	0.0085 (9)	0.0015 (9)
C8	0.0251 (13)	0.0158 (13)	0.0194 (12)	0.0006 (10)	0.0090 (10)	0.0000 (10)
C9	0.0261 (14)	0.0225 (15)	0.0221 (14)	0.0029 (11)	0.0081 (11)	0.0074 (11)
C10	0.0233 (13)	0.0113 (13)	0.0383 (16)	0.0041 (10)	0.0121 (12)	0.0096 (11)
C11	0.0248 (14)	0.0118 (13)	0.0358 (15)	−0.0002 (10)	0.0110 (12)	−0.0033 (11)
C12	0.0192 (12)	0.0131 (13)	0.0195 (13)	−0.0001 (9)	0.0059 (10)	−0.0006 (9)
C13	0.0143 (11)	0.0089 (11)	0.0164 (12)	0.0023 (9)	0.0031 (9)	0.0016 (9)
C14	0.0124 (11)	0.0206 (14)	0.0176 (12)	0.0033 (9)	0.0019 (10)	0.0001 (10)
C15	0.0202 (13)	0.0260 (15)	0.0165 (12)	0.0042 (10)	0.0055 (10)	0.0022 (10)
C16	0.0186 (13)	0.0194 (14)	0.0186 (13)	0.0008 (10)	−0.0043 (10)	0.0006 (10)
C17	0.0126 (12)	0.0205 (14)	0.0317 (15)	−0.0013 (10)	0.0016 (11)	0.0052 (11)
C18	0.0148 (12)	0.0143 (13)	0.0249 (13)	0.0021 (9)	0.0058 (10)	0.0033 (10)
C19	0.0144 (12)	0.0130 (12)	0.0188 (13)	−0.0007 (9)	0.0104 (10)	0.0005 (9)
C20	0.0197 (12)	0.0155 (13)	0.0243 (13)	0.0045 (10)	0.0103 (10)	0.0018 (10)
C21	0.0213 (13)	0.0188 (14)	0.0264 (14)	0.0077 (10)	0.0122 (11)	0.0070 (11)
C22	0.0165 (12)	0.0245 (14)	0.0173 (12)	0.0035 (10)	0.0074 (10)	0.0042 (10)
C23	0.0177 (12)	0.0181 (13)	0.0174 (12)	−0.0013 (10)	0.0084 (10)	−0.0015 (10)
C24	0.0157 (11)	0.0126 (12)	0.0211 (13)	0.0004 (9)	0.0112 (10)	−0.0011 (10)
C25	0.0280 (14)	0.0143 (13)	0.0257 (14)	−0.0058 (10)	0.0145 (12)	−0.0008 (10)
C26	0.0258 (14)	0.0227 (15)	0.0271 (14)	−0.0106 (11)	0.0102 (12)	−0.0079 (11)
C27	0.0231 (13)	0.0280 (15)	0.0198 (13)	−0.0027 (11)	0.0048 (10)	−0.0036 (11)
C28	0.0204 (13)	0.0173 (13)	0.0200 (12)	−0.0003 (10)	0.0070 (10)	0.0003 (10)

Geometric parameters (Å, º)

Sn1—C1	2.126 (2)	C11—H11A	0.9500
Sn1—C7	2.128 (2)	C12—H12A	0.9500
Sn1—C13	2.139 (2)	C13—C14	1.391 (4)
Sn1—O1W	2.3228 (17)	C13—C18	1.399 (3)
Sn1—Cl1	2.5222 (6)	C14—C15	1.395 (4)
O1W—H11	0.835 (10)	C14—H14	0.9500
O1W—H12	0.833 (10)	C15—C16	1.385 (4)
N1—C28	1.336 (3)	C15—H15	0.9500
N1—C24	1.345 (3)	C16—C17	1.387 (4)
N2—C23	1.338 (3)	C16—H16	0.9500
N2—C19	1.345 (3)	C17—C18	1.391 (4)
C1—C2	1.392 (3)	C17—H17	0.9500
C1—C6	1.395 (3)	C18—H18	0.9500
C2—C3	1.390 (3)	C19—C20	1.394 (3)
C2—H2	0.9500	C19—C19^i	1.489 (5)
C3—C4	1.386 (4)	C20—C21	1.389 (4)
C3—H3	0.9500	C20—H20	0.9500
C4—C5	1.385 (4)	C21—C22	1.386 (4)
C4—H4	0.9500	C21—H21	0.9500
C5—C6	1.388 (3)	C22—C23	1.380 (3)
C5—H5	0.9500	C22—H22	0.9500
C6—H6	0.9500	C23—H23	0.9500
C7—C12	1.391 (3)	C24—C25	1.391 (3)
C7—C8	1.396 (3)	C24—C24^i	1.488 (5)
C8—C9	1.378 (4)	C25—C26	1.385 (4)
C8—H8	0.9500	C25—H25	0.9500
C9—C10	1.382 (4)	C26—C27	1.380 (4)
C9—H9	0.9500	C26—H26	0.9500
C10—C11	1.385 (4)	C27—C28	1.381 (4)
C10—H10	0.9500	C27—H27	0.9500
C11—C12	1.391 (3)	C28—H28	0.9500
C1—Sn1—C7	125.40 (9)	C11—C12—H12A	119.6
C1—Sn1—C13	118.49 (9)	C14—C13—C18	118.4 (2)
C7—Sn1—C13	115.16 (9)	C14—C13—Sn1	120.47 (17)
C1—Sn1—O1W	85.23 (7)	C18—C13—Sn1	121.16 (19)
C7—Sn1—O1W	84.83 (7)	C13—C14—C15	121.0 (2)
C13—Sn1—O1W	90.58 (8)	C13—C14—H14	119.5
C1—Sn1—Cl1	90.80 (6)	C15—C14—H14	119.5
C7—Sn1—Cl1	92.34 (6)	C16—C15—C14	120.0 (3)
C13—Sn1—Cl1	96.90 (7)	C16—C15—H15	120.0
O1W—Sn1—Cl1	172.51 (5)	C14—C15—H15	120.0
Sn1—O1W—H11	122 (2)	C15—C16—C17	119.6 (2)
Sn1—O1W—H12	122 (2)	C15—C16—H16	120.2
H11—O1W—H12	106 (3)	C17—C16—H16	120.2
C28—N1—C24	117.7 (2)	C16—C17—C18	120.4 (2)
C23—N2—C19	117.4 (2)	C16—C17—H17	119.8
C2—C1—C6	118.3 (2)	C18—C17—H17	119.8
C2—C1—Sn1	120.88 (17)	C17—C18—C13	120.6 (3)
C6—C1—Sn1	120.68 (17)	C17—C18—H18	119.7
C3—C2—C1	121.4 (2)	C13—C18—H18	119.7
C3—C2—H2	119.3	N2—C19—C20	122.3 (2)
C1—C2—H2	119.3	N2—C19—C19^i	115.83 (15)
C4—C3—C2	119.3 (2)	C20—C19—C19^i	121.87 (16)
C4—C3—H3	120.4	C21—C20—C19	119.2 (2)
C2—C3—H3	120.4	C21—C20—H20	120.4
C5—C4—C3	120.4 (2)	C19—C20—H20	120.4
C5—C4—H4	119.8	C20—C21—C22	118.6 (2)
C3—C4—H4	119.8	C20—C21—H21	120.7
C4—C5—C6	119.8 (2)	C22—C21—H21	120.7
C4—C5—H5	120.1	C23—C22—C21	118.3 (2)
C6—C5—H5	120.1	C23—C22—H22	120.8
C5—C6—C1	120.8 (2)	C21—C22—H22	120.8
C5—C6—H6	119.6	N2—C23—C22	124.2 (2)
C1—C6—H6	119.6	N2—C23—H23	117.9
C12—C7—C8	118.3 (2)	C22—C23—H23	117.9
C12—C7—Sn1	119.85 (17)	N1—C24—C25	122.0 (2)
C8—C7—Sn1	121.89 (18)	N1—C24—C24^i	116.06 (14)
C9—C8—C7	120.9 (2)	C25—C24—C24^i	121.99 (16)
C9—C8—H8	119.6	C26—C25—C24	119.4 (2)
C7—C8—H8	119.6	C26—C25—H25	120.3
C8—C9—C10	120.4 (3)	C24—C25—H25	120.3
C8—C9—H9	119.8	C25—C26—C27	118.6 (2)
C10—C9—H9	119.8	C25—C26—H26	120.7
C11—C10—C9	119.7 (2)	C27—C26—H26	120.7
C11—C10—H10	120.2	C28—C27—C26	118.6 (2)
C9—C10—H10	120.2	C28—C27—H27	120.7
C10—C11—C12	119.9 (2)	C26—C27—H27	120.7
C10—C11—H11A	120.1	N1—C28—C27	123.7 (2)
C12—C11—H11A	120.1	N1—C28—H28	118.1
C7—C12—C11	120.8 (2)	C27—C28—H28	118.1
C7—C12—H12A	119.6
C7—Sn1—C1—C2	−32.5 (2)	C1—Sn1—C13—C14	85.8 (2)
C13—Sn1—C1—C2	159.23 (18)	C7—Sn1—C13—C14	−83.7 (2)
O1W—Sn1—C1—C2	−112.70 (19)	O1W—Sn1—C13—C14	0.88 (19)
Cl1—Sn1—C1—C2	60.94 (18)	Cl1—Sn1—C13—C14	−179.54 (18)
C7—Sn1—C1—C6	151.74 (16)	C1—Sn1—C13—C18	−95.7 (2)
C13—Sn1—C1—C6	−16.5 (2)	C7—Sn1—C13—C18	94.85 (19)
O1W—Sn1—C1—C6	71.54 (18)	O1W—Sn1—C13—C18	179.40 (19)
Cl1—Sn1—C1—C6	−114.82 (18)	Cl1—Sn1—C13—C18	−1.02 (19)
C6—C1—C2—C3	0.1 (4)	C18—C13—C14—C15	−0.2 (4)
Sn1—C1—C2—C3	−175.76 (18)	Sn1—C13—C14—C15	178.39 (19)
C1—C2—C3—C4	−0.1 (4)	C13—C14—C15—C16	0.7 (4)
C2—C3—C4—C5	−0.2 (4)	C14—C15—C16—C17	−0.8 (4)
C3—C4—C5—C6	0.5 (4)	C15—C16—C17—C18	0.4 (4)
C4—C5—C6—C1	−0.6 (4)	C16—C17—C18—C13	0.1 (4)
C2—C1—C6—C5	0.3 (3)	C14—C13—C18—C17	−0.2 (4)
Sn1—C1—C6—C5	176.13 (18)	Sn1—C13—C18—C17	−178.74 (18)
C1—Sn1—C7—C12	−164.19 (17)	C23—N2—C19—C20	1.5 (3)
C13—Sn1—C7—C12	4.4 (2)	C23—N2—C19—C19^i	−178.5 (2)
O1W—Sn1—C7—C12	−83.79 (19)	N2—C19—C20—C21	−2.2 (4)
Cl1—Sn1—C7—C12	103.16 (18)	C19^i—C19—C20—C21	177.8 (3)
C1—Sn1—C7—C8	15.0 (2)	C19—C20—C21—C22	0.6 (4)
C13—Sn1—C7—C8	−176.37 (18)	C20—C21—C22—C23	1.6 (4)
O1W—Sn1—C7—C8	95.43 (19)	C19—N2—C23—C22	0.8 (4)
Cl1—Sn1—C7—C8	−77.62 (19)	C21—C22—C23—N2	−2.4 (4)
C12—C7—C8—C9	0.6 (4)	C28—N1—C24—C25	0.2 (3)
Sn1—C7—C8—C9	−178.67 (19)	C28—N1—C24—C24^i	−179.5 (2)
C7—C8—C9—C10	−1.4 (4)	N1—C24—C25—C26	0.0 (4)
C8—C9—C10—C11	1.1 (4)	C24^i—C24—C25—C26	179.6 (3)
C9—C10—C11—C12	0.1 (4)	C24—C25—C26—C27	−0.2 (4)
C8—C7—C12—C11	0.6 (4)	C25—C26—C27—C28	0.3 (4)
Sn1—C7—C12—C11	179.86 (19)	C24—N1—C28—C27	−0.1 (4)
C10—C11—C12—C7	−1.0 (4)	C26—C27—C28—N1	−0.2 (4)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···N1	0.84 (1)	1.95 (1)	2.786 (3)	176 (3)
O1w—H12···N2	0.83 (1)	1.94 (1)	2.773 (3)	176 (3)

(Sn2) Aquachlorotriphenyltin(IV)–2,2'-bipyridine (1/1)

Crystal data

Sn2Cl2(H2O)2(C6H5)6(C10H8N2)2	F(000) = 2256
Mr = 1119.28	Dx = 1.527 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 14735 reflections
a = 15.5993 (5) Å	θ = 3.7–27.5°
b = 16.1284 (4) Å	µ = 1.18 mm^−1
c = 20.4476 (7) Å	T = 100 K
β = 108.849 (4)°	Prism, colorless
V = 4868.6 (3) Å^3	0.61 × 0.55 × 0.13 mm
Z = 4

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	5640 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4804 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 2.9°
ω scan	h = −18→20
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −20→21
Tmin = 0.565, Tmax = 0.875	l = −26→26
31562 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0453P)^2 + 5.791P] where P = (Fo^2 + 2Fc^2)/3
5640 reflections	(Δ/σ)max = 0.001
306 parameters	Δρmax = 2.96 e Å^−3
2 restraints	Δρmin = −0.70 e Å^−3

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

	x	y	z	Uiso*/Ueq
Sn1	0.295817 (9)	0.599063 (8)	0.322544 (7)	0.01147 (6)
Cl1	0.16576 (4)	0.59847 (3)	0.37050 (3)	0.02088 (13)
O1W	0.42788 (11)	0.60063 (9)	0.29321 (9)	0.0136 (3)
H11	0.4606 (18)	0.6431 (13)	0.3007 (17)	0.040 (9)*
H12	0.4627 (17)	0.5600 (13)	0.3000 (16)	0.036 (9)*
N1	0.53939 (12)	0.74003 (12)	0.32052 (10)	0.0157 (4)
N2	0.54057 (12)	0.46301 (11)	0.32069 (9)	0.0144 (4)
C1	0.34148 (14)	0.71499 (13)	0.37065 (11)	0.0133 (4)
C2	0.36796 (15)	0.72326 (14)	0.44209 (11)	0.0179 (5)
H2	0.3697	0.6755	0.4697	0.021*
C3	0.39196 (16)	0.79970 (15)	0.47410 (12)	0.0217 (5)
H3	0.4089	0.8043	0.5229	0.026*
C4	0.39090 (16)	0.86932 (15)	0.43377 (14)	0.0241 (5)
H4	0.4078	0.9218	0.4551	0.029*
C5	0.36526 (15)	0.86226 (15)	0.36249 (13)	0.0207 (5)
H5	0.3646	0.9099	0.3351	0.025*
C6	0.34046 (15)	0.78558 (14)	0.33108 (12)	0.0169 (5)
H6	0.3226	0.7812	0.2822	0.020*
C7	0.34162 (14)	0.48096 (13)	0.36567 (11)	0.0130 (4)
C8	0.39032 (16)	0.47080 (15)	0.43570 (12)	0.0197 (5)
H8	0.4027	0.5177	0.4654	0.024*
C9	0.42073 (18)	0.39358 (15)	0.46245 (14)	0.0243 (5)
H9	0.4544	0.3879	0.5101	0.029*
C10	0.40237 (17)	0.32443 (15)	0.42018 (14)	0.0240 (5)
H10	0.4230	0.2713	0.4388	0.029*
C11	0.35368 (17)	0.33278 (15)	0.35046 (14)	0.0239 (5)
H11A	0.3405	0.2854	0.3213	0.029*
C12	0.32434 (17)	0.41089 (14)	0.32345 (13)	0.0181 (5)
H12A	0.2921	0.4165	0.2755	0.022*
C13	0.21562 (15)	0.59831 (12)	0.21556 (12)	0.0140 (4)
C14	0.25712 (16)	0.59761 (13)	0.16452 (13)	0.0178 (5)
H14	0.3213	0.5988	0.1775	0.021*
C15	0.20565 (17)	0.59512 (14)	0.09472 (13)	0.0210 (5)
H15	0.2349	0.5944	0.0606	0.025*
C16	0.11192 (17)	0.59374 (14)	0.07503 (13)	0.0222 (5)
H16	0.0769	0.5926	0.0274	0.027*
C17	0.06941 (17)	0.59398 (14)	0.12509 (14)	0.0231 (5)
H17	0.0052	0.5924	0.1118	0.028*
C18	0.12093 (16)	0.59654 (13)	0.19505 (13)	0.0182 (5)
H18	0.0914	0.5971	0.2290	0.022*
C19	0.53313 (15)	0.39156 (13)	0.28570 (12)	0.0149 (4)
C20	0.58388 (16)	0.32168 (15)	0.31401 (12)	0.0201 (5)
H20	0.5754	0.2713	0.2887	0.024*
C21	0.64723 (16)	0.32654 (15)	0.37981 (13)	0.0219 (5)
H21	0.6835	0.2799	0.3998	0.026*
C22	0.65658 (16)	0.40081 (14)	0.41584 (13)	0.0195 (5)
H22	0.6999	0.4066	0.4606	0.023*
C23	0.60096 (15)	0.46608 (14)	0.38460 (12)	0.0176 (5)
H23	0.6058	0.5162	0.4099	0.021*
C24	0.53166 (14)	0.81234 (13)	0.28630 (11)	0.0155 (4)
C25	0.57877 (17)	0.88300 (15)	0.31667 (13)	0.0214 (5)
H25	0.5715	0.9333	0.2913	0.026*
C26	0.63653 (17)	0.87948 (16)	0.38439 (14)	0.0241 (5)
H26	0.6701	0.9269	0.4059	0.029*
C27	0.64413 (17)	0.80504 (16)	0.41988 (13)	0.0248 (5)
H27	0.6823	0.8006	0.4665	0.030*
C28	0.59504 (16)	0.73762 (15)	0.38602 (12)	0.0191 (5)
H28	0.6010	0.6867	0.4105	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.01332 (10)	0.00855 (9)	0.01355 (9)	0.00028 (5)	0.00573 (6)	−0.00006 (5)
Cl1	0.0219 (3)	0.0159 (3)	0.0319 (3)	−0.0010 (2)	0.0186 (2)	−0.0019 (2)
O1W	0.0120 (8)	0.0087 (8)	0.0210 (8)	0.0000 (6)	0.0065 (6)	0.0004 (6)
N1	0.0164 (9)	0.0136 (9)	0.0187 (9)	−0.0008 (7)	0.0076 (7)	−0.0014 (7)
N2	0.0146 (9)	0.0124 (9)	0.0168 (9)	0.0003 (7)	0.0058 (7)	0.0017 (7)
C1	0.0108 (10)	0.0108 (10)	0.0188 (10)	0.0002 (8)	0.0054 (8)	−0.0007 (8)
C2	0.0211 (12)	0.0136 (11)	0.0163 (11)	0.0036 (9)	0.0025 (9)	0.0027 (8)
C3	0.0212 (12)	0.0210 (12)	0.0192 (11)	0.0027 (10)	0.0014 (9)	−0.0058 (10)
C4	0.0193 (12)	0.0146 (12)	0.0338 (14)	−0.0010 (9)	0.0025 (10)	−0.0087 (10)
C5	0.0166 (12)	0.0128 (11)	0.0316 (13)	0.0001 (9)	0.0063 (10)	0.0035 (10)
C6	0.0173 (12)	0.0157 (11)	0.0194 (11)	−0.0011 (9)	0.0084 (9)	0.0008 (9)
C7	0.0121 (10)	0.0110 (10)	0.0184 (10)	0.0009 (8)	0.0085 (8)	0.0022 (8)
C8	0.0266 (13)	0.0140 (11)	0.0191 (11)	0.0000 (9)	0.0081 (9)	−0.0005 (9)
C9	0.0249 (14)	0.0246 (13)	0.0229 (13)	0.0021 (10)	0.0070 (10)	0.0068 (10)
C10	0.0223 (13)	0.0116 (11)	0.0376 (14)	0.0030 (9)	0.0089 (11)	0.0093 (10)
C11	0.0251 (13)	0.0117 (11)	0.0363 (14)	−0.0008 (9)	0.0116 (11)	−0.0041 (10)
C12	0.0189 (12)	0.0140 (11)	0.0214 (12)	−0.0017 (9)	0.0064 (9)	−0.0021 (9)
C13	0.0147 (11)	0.0082 (10)	0.0167 (11)	0.0010 (8)	0.0018 (8)	0.0012 (8)
C14	0.0123 (11)	0.0198 (12)	0.0200 (12)	0.0019 (8)	0.0035 (9)	−0.0001 (9)
C15	0.0221 (13)	0.0247 (13)	0.0157 (11)	0.0039 (9)	0.0056 (10)	0.0015 (9)
C16	0.0197 (13)	0.0191 (12)	0.0203 (12)	0.0009 (9)	−0.0040 (9)	0.0020 (9)
C17	0.0123 (12)	0.0203 (13)	0.0318 (14)	−0.0009 (9)	0.0002 (10)	0.0050 (10)
C18	0.0138 (12)	0.0148 (11)	0.0253 (13)	0.0011 (8)	0.0056 (9)	0.0021 (9)
C19	0.0136 (11)	0.0147 (11)	0.0193 (12)	−0.0003 (8)	0.0091 (9)	0.0011 (8)
C20	0.0239 (13)	0.0148 (11)	0.0245 (12)	0.0024 (9)	0.0120 (10)	0.0019 (9)
C21	0.0204 (12)	0.0209 (12)	0.0268 (12)	0.0086 (9)	0.0111 (10)	0.0078 (10)
C22	0.0161 (12)	0.0245 (13)	0.0182 (12)	0.0031 (9)	0.0063 (9)	0.0047 (9)
C23	0.0195 (12)	0.0176 (11)	0.0180 (11)	−0.0006 (9)	0.0094 (9)	0.0011 (9)
C24	0.0155 (11)	0.0126 (11)	0.0217 (11)	0.0013 (8)	0.0108 (9)	−0.0003 (8)
C25	0.0264 (13)	0.0155 (11)	0.0257 (13)	−0.0059 (9)	0.0131 (10)	−0.0013 (9)
C26	0.0239 (13)	0.0214 (12)	0.0284 (13)	−0.0104 (10)	0.0102 (10)	−0.0083 (10)
C27	0.0238 (13)	0.0283 (14)	0.0200 (12)	−0.0040 (10)	0.0041 (9)	−0.0037 (10)
C28	0.0224 (12)	0.0164 (11)	0.0192 (11)	0.0001 (9)	0.0075 (9)	−0.0002 (9)

Geometric parameters (Å, º)

Sn1—C7	2.123 (2)	C11—H11A	0.9500
Sn1—C1	2.126 (2)	C12—H12A	0.9500
Sn1—C13	2.141 (2)	C13—C14	1.395 (3)
Sn1—O1W	2.3245 (16)	C13—C18	1.399 (3)
Sn1—Cl1	2.5225 (6)	C14—C15	1.394 (3)
O1W—H11	0.839 (10)	C14—H14	0.9500
O1W—H12	0.834 (10)	C15—C16	1.386 (4)
N1—C28	1.341 (3)	C15—H15	0.9500
N1—C24	1.345 (3)	C16—C17	1.388 (4)
N2—C19	1.342 (3)	C16—H16	0.9500
N2—C23	1.342 (3)	C17—C18	1.397 (4)
C1—C2	1.390 (3)	C17—H17	0.9500
C1—C6	1.394 (3)	C18—H18	0.9500
C2—C3	1.389 (3)	C19—C20	1.391 (3)
C2—H2	0.9500	C19—C19^i	1.492 (5)
C3—C4	1.390 (4)	C20—C21	1.391 (3)
C3—H3	0.9500	C20—H20	0.9500
C4—C5	1.386 (4)	C21—C22	1.389 (3)
C4—H4	0.9500	C21—H21	0.9500
C5—C6	1.390 (3)	C22—C23	1.382 (3)
C5—H5	0.9500	C22—H22	0.9500
C6—H6	0.9500	C23—H23	0.9500
C7—C12	1.395 (3)	C24—C25	1.389 (3)
C7—C8	1.397 (3)	C24—C24^i	1.494 (4)
C8—C9	1.381 (3)	C25—C26	1.388 (4)
C8—H8	0.9500	C25—H25	0.9500
C9—C10	1.383 (4)	C26—C27	1.388 (4)
C9—H9	0.9500	C26—H26	0.9500
C10—C11	1.389 (4)	C27—C28	1.380 (3)
C10—H10	0.9500	C27—H27	0.9500
C11—C12	1.392 (3)	C28—H28	0.9500
C7—Sn1—C1	125.40 (9)	C7—C12—H12A	119.5
C7—Sn1—C13	115.24 (8)	C14—C13—C18	118.4 (2)
C1—Sn1—C13	118.41 (8)	C14—C13—Sn1	120.36 (16)
C7—Sn1—O1W	84.81 (7)	C18—C13—Sn1	121.21 (18)
C1—Sn1—O1W	85.27 (7)	C13—C14—C15	120.9 (2)
C13—Sn1—O1W	90.60 (8)	C13—C14—H14	119.6
C7—Sn1—Cl1	92.30 (6)	C15—C14—H14	119.6
C1—Sn1—Cl1	90.85 (6)	C16—C15—C14	120.2 (2)
C13—Sn1—Cl1	96.85 (6)	C16—C15—H15	119.9
O1W—Sn1—Cl1	172.54 (4)	C14—C15—H15	119.9
Sn1—O1W—H11	120 (2)	C15—C16—C17	119.8 (2)
Sn1—O1W—H12	122 (2)	C15—C16—H16	120.1
H11—O1W—H12	107 (3)	C17—C16—H16	120.1
C28—N1—C24	117.7 (2)	C16—C17—C18	120.1 (2)
C19—N2—C23	117.61 (19)	C16—C17—H17	119.9
C2—C1—C6	118.4 (2)	C18—C17—H17	119.9
C2—C1—Sn1	120.81 (16)	C17—C18—C13	120.7 (2)
C6—C1—Sn1	120.70 (16)	C17—C18—H18	119.7
C1—C2—C3	121.6 (2)	C13—C18—H18	119.7
C1—C2—H2	119.2	N2—C19—C20	122.3 (2)
C3—C2—H2	119.2	N2—C19—C19^i	115.80 (14)
C2—C3—C4	119.2 (2)	C20—C19—C19^i	121.90 (15)
C2—C3—H3	120.4	C19—C20—C21	119.2 (2)
C4—C3—H3	120.4	C19—C20—H20	120.4
C5—C4—C3	120.1 (2)	C21—C20—H20	120.4
C5—C4—H4	119.9	C22—C21—C20	118.8 (2)
C3—C4—H4	119.9	C22—C21—H21	120.6
C4—C5—C6	120.1 (2)	C20—C21—H21	120.6
C4—C5—H5	119.9	C23—C22—C21	118.0 (2)
C6—C5—H5	119.9	C23—C22—H22	121.0
C5—C6—C1	120.6 (2)	C21—C22—H22	121.0
C5—C6—H6	119.7	N2—C23—C22	124.1 (2)
C1—C6—H6	119.7	N2—C23—H23	118.0
C12—C7—C8	118.2 (2)	C22—C23—H23	118.0
C12—C7—Sn1	119.87 (16)	N1—C24—C25	122.2 (2)
C8—C7—Sn1	121.97 (16)	N1—C24—C24^i	115.86 (13)
C9—C8—C7	121.0 (2)	C25—C24—C24^i	121.91 (15)
C9—C8—H8	119.5	C26—C25—C24	119.4 (2)
C7—C8—H8	119.5	C26—C25—H25	120.3
C8—C9—C10	120.3 (2)	C24—C25—H25	120.3
C8—C9—H9	119.9	C25—C26—C27	118.4 (2)
C10—C9—H9	119.9	C25—C26—H26	120.8
C9—C10—C11	119.8 (2)	C27—C26—H26	120.8
C9—C10—H10	120.1	C28—C27—C26	118.6 (2)
C11—C10—H10	120.1	C28—C27—H27	120.7
C10—C11—C12	119.7 (2)	C26—C27—H27	120.7
C10—C11—H11A	120.1	N1—C28—C27	123.6 (2)
C12—C11—H11A	120.1	N1—C28—H28	118.2
C11—C12—C7	121.0 (2)	C27—C28—H28	118.2
C11—C12—H12A	119.5
C7—Sn1—C1—C2	−32.1 (2)	C7—Sn1—C13—C14	−83.58 (18)
C13—Sn1—C1—C2	159.56 (17)	C1—Sn1—C13—C14	85.90 (18)
O1W—Sn1—C1—C2	−112.33 (18)	O1W—Sn1—C13—C14	0.97 (17)
Cl1—Sn1—C1—C2	61.29 (17)	Cl1—Sn1—C13—C14	−179.39 (16)
C7—Sn1—C1—C6	151.71 (15)	C7—Sn1—C13—C18	94.91 (18)
C13—Sn1—C1—C6	−16.6 (2)	C1—Sn1—C13—C18	−95.61 (18)
O1W—Sn1—C1—C6	71.51 (17)	O1W—Sn1—C13—C18	179.45 (17)
Cl1—Sn1—C1—C6	−114.86 (17)	Cl1—Sn1—C13—C18	−0.91 (17)
C6—C1—C2—C3	0.8 (3)	C18—C13—C14—C15	−0.1 (3)
Sn1—C1—C2—C3	−175.46 (17)	Sn1—C13—C14—C15	178.46 (16)
C1—C2—C3—C4	−1.1 (4)	C13—C14—C15—C16	0.3 (3)
C2—C3—C4—C5	0.6 (4)	C14—C15—C16—C17	−0.7 (4)
C3—C4—C5—C6	0.1 (4)	C15—C16—C17—C18	0.7 (4)
C4—C5—C6—C1	−0.3 (3)	C16—C17—C18—C13	−0.4 (3)
C2—C1—C6—C5	−0.1 (3)	C14—C13—C18—C17	0.1 (3)
Sn1—C1—C6—C5	176.17 (16)	Sn1—C13—C18—C17	−178.40 (16)
C1—Sn1—C7—C12	−164.07 (16)	C23—N2—C19—C20	1.4 (3)
C13—Sn1—C7—C12	4.6 (2)	C23—N2—C19—C19^i	−178.6 (2)
O1W—Sn1—C7—C12	−83.64 (18)	N2—C19—C20—C21	−2.6 (3)
Cl1—Sn1—C7—C12	103.26 (17)	C19^i—C19—C20—C21	177.4 (2)
C1—Sn1—C7—C8	15.0 (2)	C19—C20—C21—C22	1.2 (3)
C13—Sn1—C7—C8	−176.37 (17)	C20—C21—C22—C23	1.0 (3)
O1W—Sn1—C7—C8	95.42 (18)	C19—N2—C23—C22	1.1 (3)
Cl1—Sn1—C7—C8	−77.68 (18)	C21—C22—C23—N2	−2.3 (3)
C12—C7—C8—C9	0.1 (3)	C28—N1—C24—C25	−0.2 (3)
Sn1—C7—C8—C9	−178.95 (18)	C28—N1—C24—C24^i	−179.5 (2)
C7—C8—C9—C10	−0.8 (4)	N1—C24—C25—C26	0.5 (4)
C8—C9—C10—C11	0.4 (4)	C24^i—C24—C25—C26	179.8 (2)
C9—C10—C11—C12	0.5 (4)	C24—C25—C26—C27	−0.9 (4)
C10—C11—C12—C7	−1.2 (4)	C25—C26—C27—C28	0.9 (4)
C8—C7—C12—C11	0.9 (3)	C24—N1—C28—C27	0.2 (3)
Sn1—C7—C12—C11	179.97 (18)	C26—C27—C28—N1	−0.6 (4)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···N1	0.84 (1)	1.95 (1)	2.787 (2)	178 (3)
O1w—H12···N2	0.83 (1)	1.94 (1)	2.774 (2)	176 (3)

(Sn3) Aquachlorotriphenyltin(IV)–2,2'-bipyridine (1/1)

Crystal data

Sn2Cl2(H2O)2(C6H5)6(C10H8N2)2	F(000) = 2256
Mr = 1119.28	Dx = 1.533 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 14938 reflections
a = 15.5742 (4) Å	θ = 3.8–27.5°
b = 16.1161 (4) Å	µ = 1.19 mm^−1
c = 20.4181 (6) Å	T = 100 K
β = 108.879 (3)°	Prism, colorless
V = 4849.2 (2) Å^3	0.33 × 0.26 × 0.15 mm
Z = 4

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	5610 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4855 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.034
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 2.9°
ω scan	h = −20→20
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −20→20
Tmin = 0.765, Tmax = 0.856	l = −26→26
32969 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.044P)^2 + 7.5426P] where P = (Fo^2 + 2Fc^2)/3
5610 reflections	(Δ/σ)max = 0.001
306 parameters	Δρmax = 2.68 e Å^−3
2 restraints	Δρmin = −0.40 e Å^−3

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

	x	y	z	Uiso*/Ueq
Sn1	0.295805 (9)	0.599064 (8)	0.322534 (7)	0.01149 (6)
Cl1	0.16577 (4)	0.59854 (3)	0.37050 (3)	0.02091 (12)
O1W	0.42787 (10)	0.60058 (8)	0.29325 (9)	0.0137 (3)
H11	0.4613 (17)	0.6422 (12)	0.2980 (16)	0.035 (8)*
H12	0.4629 (16)	0.5601 (12)	0.2993 (16)	0.034 (8)*
N1	0.53943 (11)	0.74011 (11)	0.32060 (10)	0.0155 (3)
N2	0.54075 (11)	0.46317 (10)	0.32085 (9)	0.0140 (3)
C1	0.34145 (13)	0.71503 (12)	0.37076 (11)	0.0132 (4)
C2	0.36779 (14)	0.72348 (13)	0.44231 (11)	0.0178 (4)
H2	0.3691	0.6758	0.4700	0.021*
C3	0.39217 (15)	0.79980 (14)	0.47419 (12)	0.0226 (5)
H3	0.4095	0.8045	0.5231	0.027*
C4	0.39086 (15)	0.86919 (14)	0.43373 (13)	0.0236 (5)
H4	0.4077	0.9217	0.4551	0.028*
C5	0.36524 (14)	0.86250 (14)	0.36239 (13)	0.0207 (5)
H5	0.3645	0.9102	0.3349	0.025*
C6	0.34057 (14)	0.78534 (13)	0.33108 (12)	0.0170 (4)
H6	0.3230	0.7808	0.2821	0.020*
C7	0.34155 (13)	0.48069 (12)	0.36565 (11)	0.0138 (4)
C8	0.39023 (15)	0.47069 (14)	0.43568 (12)	0.0201 (4)
H8	0.4024	0.5176	0.4654	0.024*
C9	0.42098 (17)	0.39332 (14)	0.46237 (13)	0.0234 (5)
H9	0.4551	0.3877	0.5100	0.028*
C10	0.40224 (16)	0.32420 (14)	0.42008 (14)	0.0239 (5)
H10	0.4226	0.2710	0.4387	0.029*
C11	0.35363 (16)	0.33277 (14)	0.35049 (13)	0.0232 (5)
H11A	0.3403	0.2854	0.3213	0.028*
C12	0.32417 (15)	0.41099 (13)	0.32324 (12)	0.0177 (4)
H12A	0.2919	0.4167	0.2753	0.021*
C13	0.21565 (14)	0.59823 (11)	0.21568 (12)	0.0142 (4)
C14	0.25711 (15)	0.59770 (12)	0.16449 (12)	0.0176 (4)
H14	0.3214	0.5992	0.1775	0.021*
C15	0.20548 (15)	0.59497 (14)	0.09453 (12)	0.0210 (5)
H15	0.2347	0.5940	0.0603	0.025*
C16	0.11146 (16)	0.59374 (13)	0.07487 (13)	0.0219 (5)
H16	0.0762	0.5928	0.0272	0.026*
C17	0.06937 (15)	0.59387 (13)	0.12509 (14)	0.0231 (5)
H17	0.0050	0.5923	0.1118	0.028*
C18	0.12080 (15)	0.59634 (12)	0.19507 (13)	0.0183 (5)
H18	0.0912	0.5967	0.2291	0.022*
C19	0.53306 (14)	0.39160 (12)	0.28555 (11)	0.0147 (4)
C20	0.58409 (15)	0.32173 (13)	0.31410 (12)	0.0195 (4)
H20	0.5757	0.2713	0.2888	0.023*
C21	0.64714 (15)	0.32656 (14)	0.37979 (12)	0.0216 (5)
H21	0.6833	0.2798	0.3998	0.026*
C22	0.65660 (15)	0.40058 (13)	0.41576 (12)	0.0188 (5)
H22	0.6999	0.4062	0.4606	0.023*
C23	0.60122 (14)	0.46611 (13)	0.38451 (11)	0.0171 (4)
H23	0.6065	0.5164	0.4098	0.020*
C24	0.53141 (13)	0.81216 (12)	0.28619 (11)	0.0154 (4)
C25	0.57890 (16)	0.88314 (14)	0.31674 (13)	0.0211 (5)
H25	0.5718	0.9335	0.2914	0.025*
C26	0.63645 (16)	0.87930 (15)	0.38445 (13)	0.0251 (5)
H26	0.6700	0.9267	0.4061	0.030*
C27	0.64420 (16)	0.80519 (15)	0.42007 (12)	0.0247 (5)
H27	0.6824	0.8008	0.4668	0.030*
C28	0.59497 (15)	0.73769 (14)	0.38584 (12)	0.0200 (4)
H28	0.6011	0.6867	0.4102	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.01254 (8)	0.00887 (9)	0.01403 (9)	0.00030 (5)	0.00565 (6)	−0.00008 (5)
Cl1	0.0210 (3)	0.0166 (3)	0.0320 (3)	−0.00103 (19)	0.0182 (2)	−0.0018 (2)
O1W	0.0103 (7)	0.0086 (7)	0.0233 (8)	0.0003 (5)	0.0068 (6)	0.0006 (6)
N1	0.0150 (8)	0.0134 (8)	0.0192 (9)	−0.0017 (7)	0.0072 (7)	−0.0012 (7)
N2	0.0130 (8)	0.0123 (8)	0.0177 (8)	0.0005 (7)	0.0066 (7)	0.0015 (7)
C1	0.0107 (9)	0.0112 (9)	0.0181 (10)	−0.0003 (7)	0.0054 (7)	−0.0018 (8)
C2	0.0215 (10)	0.0148 (10)	0.0154 (10)	0.0043 (8)	0.0036 (8)	0.0026 (8)
C3	0.0212 (10)	0.0207 (11)	0.0220 (11)	0.0015 (9)	0.0016 (9)	−0.0061 (10)
C4	0.0186 (10)	0.0134 (10)	0.0345 (13)	−0.0008 (9)	0.0025 (9)	−0.0079 (10)
C5	0.0162 (10)	0.0137 (10)	0.0315 (13)	−0.0005 (8)	0.0069 (9)	0.0026 (9)
C6	0.0165 (10)	0.0149 (10)	0.0208 (11)	−0.0012 (8)	0.0078 (8)	−0.0002 (8)
C7	0.0130 (9)	0.0108 (9)	0.0187 (10)	0.0004 (7)	0.0068 (8)	0.0026 (8)
C8	0.0246 (11)	0.0155 (10)	0.0209 (11)	−0.0003 (9)	0.0083 (9)	−0.0004 (9)
C9	0.0251 (12)	0.0223 (12)	0.0230 (12)	0.0028 (9)	0.0081 (10)	0.0080 (9)
C10	0.0221 (11)	0.0113 (10)	0.0374 (14)	0.0031 (9)	0.0085 (10)	0.0082 (9)
C11	0.0240 (11)	0.0115 (10)	0.0349 (13)	−0.0005 (9)	0.0106 (10)	−0.0040 (9)
C12	0.0183 (10)	0.0127 (10)	0.0211 (11)	0.0002 (8)	0.0048 (8)	0.0002 (8)
C13	0.0144 (10)	0.0100 (9)	0.0171 (10)	0.0013 (7)	0.0034 (8)	0.0007 (8)
C14	0.0125 (9)	0.0196 (11)	0.0191 (11)	0.0029 (8)	0.0030 (8)	0.0000 (8)
C15	0.0188 (11)	0.0261 (12)	0.0167 (11)	0.0042 (9)	0.0038 (9)	0.0006 (9)
C16	0.0180 (11)	0.0209 (12)	0.0200 (11)	0.0009 (9)	−0.0031 (9)	0.0014 (9)
C17	0.0122 (10)	0.0211 (12)	0.0310 (13)	−0.0001 (8)	0.0001 (9)	0.0049 (9)
C18	0.0137 (10)	0.0159 (11)	0.0251 (12)	0.0014 (8)	0.0059 (9)	0.0042 (8)
C19	0.0120 (9)	0.0149 (10)	0.0199 (11)	−0.0011 (7)	0.0090 (9)	0.0011 (8)
C20	0.0214 (11)	0.0132 (10)	0.0265 (12)	0.0034 (8)	0.0113 (9)	0.0014 (9)
C21	0.0192 (10)	0.0202 (11)	0.0278 (12)	0.0094 (9)	0.0110 (9)	0.0078 (9)
C22	0.0152 (10)	0.0245 (12)	0.0175 (11)	0.0029 (8)	0.0064 (8)	0.0045 (9)
C23	0.0175 (10)	0.0168 (10)	0.0183 (10)	−0.0010 (8)	0.0076 (8)	0.0004 (8)
C24	0.0150 (9)	0.0126 (10)	0.0219 (11)	0.0009 (8)	0.0106 (8)	−0.0017 (8)
C25	0.0255 (11)	0.0147 (10)	0.0262 (12)	−0.0046 (9)	0.0127 (10)	−0.0007 (9)
C26	0.0248 (12)	0.0231 (11)	0.0287 (13)	−0.0093 (10)	0.0105 (10)	−0.0068 (10)
C27	0.0235 (11)	0.0284 (12)	0.0201 (11)	−0.0040 (10)	0.0042 (9)	−0.0042 (10)
C28	0.0222 (11)	0.0179 (11)	0.0203 (11)	−0.0001 (9)	0.0076 (9)	0.0000 (9)

Geometric parameters (Å, º)

Sn1—C1	2.125 (2)	C11—H11A	0.9500
Sn1—C7	2.125 (2)	C12—H12A	0.9500
Sn1—C13	2.135 (2)	C13—C14	1.395 (3)
Sn1—O1W	2.3204 (15)	C13—C18	1.399 (3)
Sn1—Cl1	2.5187 (5)	C14—C15	1.395 (3)
O1W—H11	0.835 (10)	C14—H14	0.9500
O1W—H12	0.833 (10)	C15—C16	1.388 (3)
N1—C28	1.334 (3)	C15—H15	0.9500
N1—C24	1.342 (3)	C16—C17	1.384 (4)
N2—C23	1.336 (3)	C16—H16	0.9500
N2—C19	1.345 (3)	C17—C18	1.394 (3)
C1—C2	1.391 (3)	C17—H17	0.9500
C1—C6	1.390 (3)	C18—H18	0.9500
C2—C3	1.386 (3)	C19—C20	1.393 (3)
C2—H2	0.9500	C19—C19^i	1.483 (4)
C3—C4	1.387 (3)	C20—C21	1.385 (3)
C3—H3	0.9500	C20—H20	0.9500
C4—C5	1.384 (3)	C21—C22	1.384 (3)
C4—H4	0.9500	C21—H21	0.9500
C5—C6	1.394 (3)	C22—C23	1.382 (3)
C5—H5	0.9500	C22—H22	0.9500
C6—H6	0.9500	C23—H23	0.9500
C7—C12	1.390 (3)	C24—C25	1.395 (3)
C7—C8	1.394 (3)	C24—C24^i	1.485 (4)
C8—C9	1.383 (3)	C25—C26	1.384 (4)
C8—H8	0.9500	C25—H25	0.9500
C9—C10	1.382 (3)	C26—C27	1.383 (4)
C9—H9	0.9500	C26—H26	0.9500
C10—C11	1.384 (4)	C27—C28	1.383 (3)
C10—H10	0.9500	C27—H27	0.9500
C11—C12	1.394 (3)	C28—H28	0.9500
C1—Sn1—C7	125.49 (8)	C11—C12—H12A	119.7
C1—Sn1—C13	118.46 (7)	C14—C13—C18	118.3 (2)
C7—Sn1—C13	115.13 (8)	C14—C13—Sn1	120.42 (15)
C1—Sn1—O1W	85.33 (6)	C18—C13—Sn1	121.26 (17)
C7—Sn1—O1W	84.83 (6)	C13—C14—C15	120.9 (2)
C13—Sn1—O1W	90.61 (7)	C13—C14—H14	119.5
C1—Sn1—Cl1	90.76 (5)	C15—C14—H14	119.5
C7—Sn1—Cl1	92.29 (5)	C16—C15—C14	120.1 (2)
C13—Sn1—Cl1	96.86 (6)	C16—C15—H15	120.0
O1W—Sn1—Cl1	172.52 (4)	C14—C15—H15	120.0
Sn1—O1W—H11	123 (2)	C17—C16—C15	119.6 (2)
Sn1—O1W—H12	123 (2)	C17—C16—H16	120.2
H11—O1W—H12	105 (3)	C15—C16—H16	120.2
C28—N1—C24	117.96 (19)	C16—C17—C18	120.4 (2)
C23—N2—C19	117.66 (18)	C16—C17—H17	119.8
C2—C1—C6	118.45 (19)	C18—C17—H17	119.8
C2—C1—Sn1	120.91 (15)	C17—C18—C13	120.6 (2)
C6—C1—Sn1	120.54 (15)	C17—C18—H18	119.7
C3—C2—C1	121.5 (2)	C13—C18—H18	119.7
C3—C2—H2	119.2	N2—C19—C20	122.0 (2)
C1—C2—H2	119.2	N2—C19—C19^i	115.97 (13)
C2—C3—C4	119.1 (2)	C20—C19—C19^i	122.07 (15)
C2—C3—H3	120.4	C21—C20—C19	119.3 (2)
C4—C3—H3	120.4	C21—C20—H20	120.3
C5—C4—C3	120.5 (2)	C19—C20—H20	120.3
C5—C4—H4	119.7	C20—C21—C22	118.9 (2)
C3—C4—H4	119.7	C20—C21—H21	120.6
C4—C5—C6	119.7 (2)	C22—C21—H21	120.6
C4—C5—H5	120.2	C23—C22—C21	118.1 (2)
C6—C5—H5	120.2	C23—C22—H22	121.0
C1—C6—C5	120.7 (2)	C21—C22—H22	121.0
C1—C6—H6	119.7	N2—C23—C22	124.1 (2)
C5—C6—H6	119.7	N2—C23—H23	118.0
C12—C7—C8	118.49 (19)	C22—C23—H23	118.0
C12—C7—Sn1	119.71 (16)	N1—C24—C25	122.0 (2)
C8—C7—Sn1	121.79 (15)	N1—C24—C24^i	116.15 (13)
C9—C8—C7	120.8 (2)	C25—C24—C24^i	121.89 (14)
C9—C8—H8	119.6	C26—C25—C24	119.2 (2)
C7—C8—H8	119.6	C26—C25—H25	120.4
C10—C9—C8	120.3 (2)	C24—C25—H25	120.4
C10—C9—H9	119.9	C25—C26—C27	118.8 (2)
C8—C9—H9	119.9	C25—C26—H26	120.6
C11—C10—C9	119.7 (2)	C27—C26—H26	120.6
C11—C10—H10	120.1	C28—C27—C26	118.3 (2)
C9—C10—H10	120.1	C28—C27—H27	120.9
C10—C11—C12	120.0 (2)	C26—C27—H27	120.9
C10—C11—H11A	120.0	N1—C28—C27	123.8 (2)
C12—C11—H11A	120.0	N1—C28—H28	118.1
C7—C12—C11	120.6 (2)	C27—C28—H28	118.1
C7—C12—H12A	119.7
C7—Sn1—C1—C2	−32.2 (2)	C1—Sn1—C13—C14	85.82 (17)
C13—Sn1—C1—C2	159.37 (15)	C7—Sn1—C13—C14	−83.78 (17)
O1W—Sn1—C1—C2	−112.47 (16)	O1W—Sn1—C13—C14	0.80 (15)
Cl1—Sn1—C1—C2	61.14 (16)	Cl1—Sn1—C13—C14	−179.57 (15)
C7—Sn1—C1—C6	151.58 (14)	C1—Sn1—C13—C18	−95.62 (16)
C13—Sn1—C1—C6	−16.84 (19)	C7—Sn1—C13—C18	94.78 (16)
O1W—Sn1—C1—C6	71.33 (16)	O1W—Sn1—C13—C18	179.35 (16)
Cl1—Sn1—C1—C6	−115.07 (15)	Cl1—Sn1—C13—C18	−1.01 (16)
C6—C1—C2—C3	0.5 (3)	C18—C13—C14—C15	−0.3 (3)
Sn1—C1—C2—C3	−175.81 (16)	Sn1—C13—C14—C15	178.32 (15)
C1—C2—C3—C4	−0.5 (3)	C13—C14—C15—C16	0.8 (3)
C2—C3—C4—C5	0.2 (3)	C14—C15—C16—C17	−1.0 (3)
C3—C4—C5—C6	0.0 (3)	C15—C16—C17—C18	0.9 (3)
C2—C1—C6—C5	−0.2 (3)	C16—C17—C18—C13	−0.4 (3)
Sn1—C1—C6—C5	176.08 (15)	C14—C13—C18—C17	0.1 (3)
C4—C5—C6—C1	0.0 (3)	Sn1—C13—C18—C17	−178.50 (15)
C1—Sn1—C7—C12	−164.07 (15)	C23—N2—C19—C20	1.6 (3)
C13—Sn1—C7—C12	4.69 (19)	C23—N2—C19—C19^i	−178.5 (2)
O1W—Sn1—C7—C12	−83.56 (17)	N2—C19—C20—C21	−2.4 (3)
Cl1—Sn1—C7—C12	103.36 (16)	C19^i—C19—C20—C21	177.6 (2)
C1—Sn1—C7—C8	14.9 (2)	C19—C20—C21—C22	1.1 (3)
C13—Sn1—C7—C8	−176.34 (16)	C20—C21—C22—C23	1.0 (3)
O1W—Sn1—C7—C8	95.41 (17)	C19—N2—C23—C22	0.6 (3)
Cl1—Sn1—C7—C8	−77.67 (16)	C21—C22—C23—N2	−1.9 (3)
C12—C7—C8—C9	0.3 (3)	C28—N1—C24—C25	−0.1 (3)
Sn1—C7—C8—C9	−178.65 (17)	C28—N1—C24—C24^i	−179.7 (2)
C7—C8—C9—C10	−1.3 (4)	N1—C24—C25—C26	0.3 (3)
C8—C9—C10—C11	1.0 (4)	C24^i—C24—C25—C26	179.9 (2)
C9—C10—C11—C12	0.3 (3)	C24—C25—C26—C27	−0.8 (3)
C8—C7—C12—C11	1.0 (3)	C25—C26—C27—C28	1.0 (3)
Sn1—C7—C12—C11	179.97 (17)	C24—N1—C28—C27	0.4 (3)
C10—C11—C12—C7	−1.3 (3)	C26—C27—C28—N1	−0.9 (4)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···N1	0.84 (1)	1.96 (1)	2.786 (2)	173 (3)
O1w—H12···N2	0.83 (1)	1.94 (1)	2.770 (2)	175 (3)

(Sn4) Aquachlorotriphenyltin(IV)–2,2'-bipyridine (1/1)

Crystal data

Sn2Cl2(H2O)2(C6H5)6(C10H8N2)2	F(000) = 2256
Mr = 1119.28	Dx = 1.531 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8808 reflections
a = 15.5844 (7) Å	θ = 3.7–27.5°
b = 16.1120 (5) Å	µ = 1.19 mm^−1
c = 20.4375 (9) Å	T = 100 K
β = 108.872 (5)°	Prism, colorless
V = 4855.9 (3) Å^3	0.22 × 0.18 × 0.14 mm
Z = 4

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	5627 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4352 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.061
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 3.1°
ω scan	h = −20→20
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −20→20
Tmin = 0.804, Tmax = 0.874	l = −26→26
34595 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.042P)^2 + 8.9852P] where P = (Fo^2 + 2Fc^2)/3
5627 reflections	(Δ/σ)max = 0.002
306 parameters	Δρmax = 2.96 e Å^−3
2 restraints	Δρmin = −0.65 e Å^−3

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

	x	y	z	Uiso*/Ueq
Sn1	0.295802 (13)	0.599062 (11)	0.322541 (10)	0.01211 (8)
Cl1	0.16571 (6)	0.59848 (4)	0.37052 (4)	0.02129 (17)
O1W	0.42772 (14)	0.60059 (12)	0.29307 (11)	0.0137 (4)
H11	0.457 (2)	0.6446 (14)	0.296 (2)	0.037 (12)*
H12	0.463 (2)	0.5606 (16)	0.301 (2)	0.031 (11)*
N1	0.53925 (17)	0.74001 (15)	0.32045 (13)	0.0157 (5)
N2	0.54094 (17)	0.46318 (15)	0.32069 (13)	0.0145 (5)
C1	0.34171 (19)	0.71485 (18)	0.37096 (15)	0.0138 (6)
C2	0.3680 (2)	0.72350 (19)	0.44215 (16)	0.0191 (7)
H2	0.3697	0.6757	0.4698	0.023*
C3	0.3919 (2)	0.7997 (2)	0.47423 (17)	0.0230 (7)
H3	0.4088	0.8043	0.5231	0.028*
C4	0.3907 (2)	0.8693 (2)	0.43375 (18)	0.0237 (7)
H4	0.4076	0.9218	0.4550	0.028*
C5	0.3651 (2)	0.86216 (19)	0.36258 (18)	0.0207 (7)
H5	0.3645	0.9098	0.3351	0.025*
C6	0.3402 (2)	0.78577 (18)	0.33134 (15)	0.0165 (6)
H6	0.3220	0.7815	0.2824	0.020*
C7	0.3417 (2)	0.48077 (17)	0.36570 (15)	0.0138 (6)
C8	0.3904 (2)	0.47092 (19)	0.43571 (17)	0.0211 (7)
H8	0.4028	0.5178	0.4654	0.025*
C9	0.4206 (2)	0.3936 (2)	0.46204 (18)	0.0238 (7)
H9	0.4544	0.3880	0.5097	0.029*
C10	0.4023 (2)	0.32414 (19)	0.42004 (19)	0.0235 (7)
H10	0.4227	0.2709	0.4387	0.028*
C11	0.3539 (2)	0.33304 (19)	0.35035 (18)	0.0236 (7)
H11A	0.3410	0.2858	0.3210	0.028*
C12	0.3242 (2)	0.41108 (18)	0.32352 (17)	0.0182 (6)
H12A	0.2916	0.4168	0.2757	0.022*
C13	0.2155 (2)	0.59802 (17)	0.21572 (16)	0.0144 (6)
C14	0.2571 (2)	0.59753 (18)	0.16427 (17)	0.0193 (7)
H14	0.3213	0.5992	0.1772	0.023*
C15	0.2056 (2)	0.59469 (19)	0.09468 (17)	0.0214 (7)
H15	0.2347	0.5932	0.0604	0.026*
C16	0.1117 (2)	0.59396 (19)	0.07532 (18)	0.0224 (7)
H16	0.0764	0.5933	0.0277	0.027*
C17	0.0695 (2)	0.59421 (19)	0.12540 (18)	0.0234 (7)
H17	0.0052	0.5928	0.1122	0.028*
C18	0.1209 (2)	0.59656 (18)	0.19471 (17)	0.0185 (6)
H18	0.0912	0.5972	0.2286	0.022*
C19	0.5329 (2)	0.39145 (17)	0.28548 (16)	0.0145 (6)
C20	0.5841 (2)	0.32182 (19)	0.31381 (17)	0.0197 (7)
H20	0.5760	0.2715	0.2883	0.024*
C21	0.6472 (2)	0.3265 (2)	0.37990 (17)	0.0218 (7)
H21	0.6833	0.2797	0.4001	0.026*
C22	0.6563 (2)	0.40088 (19)	0.41564 (17)	0.0200 (7)
H22	0.6997	0.4069	0.4604	0.024*
C23	0.6007 (2)	0.46571 (19)	0.38433 (16)	0.0180 (6)
H23	0.6052	0.5157	0.4098	0.022*
C24	0.5315 (2)	0.81226 (18)	0.28638 (15)	0.0152 (6)
C25	0.5789 (2)	0.8830 (2)	0.31660 (18)	0.0229 (7)
H25	0.5720	0.9333	0.2911	0.028*
C26	0.6366 (2)	0.8794 (2)	0.38448 (18)	0.0254 (8)
H26	0.6700	0.9269	0.4061	0.031*
C27	0.6442 (2)	0.8052 (2)	0.41989 (17)	0.0251 (7)
H27	0.6826	0.8006	0.4665	0.030*
C28	0.5948 (2)	0.7381 (2)	0.38601 (16)	0.0209 (7)
H28	0.6005	0.6873	0.4106	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.01391 (13)	0.00910 (11)	0.01463 (11)	0.00040 (8)	0.00641 (8)	0.00001 (8)
Cl1	0.0217 (4)	0.0167 (4)	0.0326 (4)	−0.0009 (3)	0.0185 (3)	−0.0015 (3)
O1W	0.0107 (11)	0.0067 (10)	0.0246 (11)	0.0000 (8)	0.0071 (9)	−0.0009 (9)
N1	0.0179 (14)	0.0127 (12)	0.0180 (13)	0.0007 (10)	0.0078 (11)	−0.0009 (10)
N2	0.0138 (13)	0.0136 (13)	0.0176 (12)	−0.0001 (10)	0.0069 (10)	0.0032 (10)
C1	0.0095 (15)	0.0128 (15)	0.0195 (15)	0.0012 (11)	0.0053 (12)	0.0004 (11)
C2	0.0226 (18)	0.0151 (16)	0.0163 (15)	0.0059 (12)	0.0018 (13)	0.0038 (12)
C3	0.0233 (18)	0.0219 (17)	0.0210 (16)	0.0034 (14)	0.0034 (14)	−0.0048 (14)
C4	0.0180 (18)	0.0161 (16)	0.0314 (19)	0.0006 (13)	−0.0001 (15)	−0.0086 (14)
C5	0.0192 (18)	0.0105 (15)	0.0322 (19)	0.0000 (12)	0.0083 (15)	0.0028 (13)
C6	0.0173 (16)	0.0164 (16)	0.0167 (15)	0.0001 (12)	0.0069 (12)	0.0021 (12)
C7	0.0117 (15)	0.0118 (14)	0.0205 (15)	−0.0007 (11)	0.0088 (12)	0.0028 (11)
C8	0.0257 (19)	0.0149 (16)	0.0219 (17)	−0.0007 (13)	0.0066 (14)	0.0009 (12)
C9	0.0255 (19)	0.0235 (18)	0.0237 (17)	0.0025 (14)	0.0099 (15)	0.0078 (14)
C10	0.0207 (18)	0.0104 (15)	0.040 (2)	0.0023 (12)	0.0111 (15)	0.0117 (13)
C11	0.0232 (19)	0.0123 (15)	0.035 (2)	−0.0015 (13)	0.0096 (15)	−0.0048 (14)
C12	0.0187 (17)	0.0150 (16)	0.0207 (16)	−0.0004 (12)	0.0060 (13)	0.0009 (12)
C13	0.0146 (16)	0.0076 (14)	0.0200 (15)	−0.0014 (11)	0.0043 (12)	0.0005 (11)
C14	0.0130 (16)	0.0200 (16)	0.0235 (17)	0.0001 (12)	0.0039 (13)	−0.0001 (13)
C15	0.0256 (19)	0.0216 (17)	0.0168 (15)	0.0055 (13)	0.0065 (14)	0.0023 (12)
C16	0.0201 (18)	0.0179 (17)	0.0232 (17)	−0.0010 (13)	−0.0011 (14)	−0.0006 (13)
C17	0.0143 (17)	0.0198 (17)	0.0323 (19)	−0.0002 (13)	0.0023 (14)	0.0047 (14)
C18	0.0168 (17)	0.0133 (15)	0.0254 (17)	0.0013 (12)	0.0067 (13)	0.0024 (12)
C19	0.0126 (16)	0.0147 (15)	0.0197 (16)	−0.0013 (11)	0.0100 (13)	0.0004 (12)
C20	0.0220 (18)	0.0119 (15)	0.0288 (18)	0.0015 (12)	0.0132 (14)	0.0004 (12)
C21	0.0222 (18)	0.0197 (16)	0.0257 (17)	0.0080 (13)	0.0107 (14)	0.0086 (13)
C22	0.0158 (17)	0.0276 (18)	0.0181 (15)	0.0030 (13)	0.0074 (13)	0.0062 (13)
C23	0.0181 (17)	0.0193 (16)	0.0192 (16)	−0.0002 (12)	0.0099 (13)	0.0025 (12)
C24	0.0147 (16)	0.0134 (15)	0.0207 (16)	0.0007 (11)	0.0104 (13)	−0.0026 (12)
C25	0.029 (2)	0.0172 (16)	0.0268 (18)	−0.0041 (13)	0.0144 (15)	−0.0019 (13)
C26	0.026 (2)	0.0233 (17)	0.0298 (19)	−0.0102 (14)	0.0136 (16)	−0.0078 (14)
C27	0.0230 (18)	0.0285 (19)	0.0234 (17)	−0.0049 (15)	0.0072 (14)	−0.0051 (14)
C28	0.0256 (19)	0.0190 (16)	0.0202 (16)	−0.0023 (13)	0.0103 (14)	0.0006 (13)

Geometric parameters (Å, º)

Sn1—C7	2.125 (3)	C11—H11A	0.9500
Sn1—C1	2.124 (3)	C12—H12A	0.9500
Sn1—C13	2.137 (3)	C13—C18	1.396 (4)
Sn1—O1W	2.322 (2)	C13—C14	1.402 (4)
Sn1—Cl1	2.5215 (8)	C14—C15	1.389 (5)
O1W—H11	0.837 (10)	C14—H14	0.9500
O1W—H12	0.833 (10)	C15—C16	1.386 (5)
N1—C28	1.340 (4)	C15—H15	0.9500
N1—C24	1.342 (4)	C16—C17	1.384 (5)
N2—C23	1.333 (4)	C16—H16	0.9500
N2—C19	1.346 (4)	C17—C18	1.384 (5)
C1—C2	1.385 (4)	C17—H17	0.9500
C1—C6	1.396 (4)	C18—H18	0.9500
C2—C3	1.385 (4)	C19—C20	1.390 (4)
C2—H2	0.9500	C19—C19^i	1.481 (6)
C3—C4	1.389 (5)	C20—C21	1.392 (5)
C3—H3	0.9500	C20—H20	0.9500
C4—C5	1.383 (5)	C21—C22	1.387 (4)
C4—H4	0.9500	C21—H21	0.9500
C5—C6	1.383 (4)	C22—C23	1.376 (4)
C5—H5	0.9500	C22—H22	0.9500
C6—H6	0.9500	C23—H23	0.9500
C7—C12	1.388 (4)	C24—C25	1.390 (4)
C7—C8	1.395 (4)	C24—C24^i	1.494 (6)
C8—C9	1.377 (4)	C25—C26	1.389 (5)
C8—H8	0.9500	C25—H25	0.9500
C9—C10	1.383 (5)	C26—C27	1.383 (5)
C9—H9	0.9500	C26—H26	0.9500
C10—C11	1.387 (5)	C27—C28	1.377 (5)
C10—H10	0.9500	C27—H27	0.9500
C11—C12	1.390 (4)	C28—H28	0.9500
C7—Sn1—C1	125.23 (12)	C11—C12—H12A	119.6
C7—Sn1—C13	115.12 (11)	C18—C13—C14	117.9 (3)
C1—Sn1—C13	118.72 (11)	C18—C13—Sn1	121.7 (2)
C7—Sn1—O1W	84.82 (9)	C14—C13—Sn1	120.4 (2)
C1—Sn1—O1W	85.32 (9)	C15—C14—C13	120.9 (3)
C13—Sn1—O1W	90.59 (10)	C15—C14—H14	119.5
C7—Sn1—Cl1	92.32 (8)	C13—C14—H14	119.5
C1—Sn1—Cl1	90.81 (8)	C16—C15—C14	119.9 (3)
C13—Sn1—Cl1	96.79 (8)	C16—C15—H15	120.0
O1W—Sn1—Cl1	172.61 (6)	C14—C15—H15	120.0
Sn1—O1W—H11	120 (3)	C17—C16—C15	119.9 (3)
Sn1—O1W—H12	122 (3)	C17—C16—H16	120.0
H11—O1W—H12	109 (4)	C15—C16—H16	120.0
C28—N1—C24	117.3 (3)	C16—C17—C18	120.1 (3)
C23—N2—C19	117.6 (3)	C16—C17—H17	120.0
C2—C1—C6	118.1 (3)	C18—C17—H17	120.0
C2—C1—Sn1	121.2 (2)	C17—C18—C13	121.2 (3)
C6—C1—Sn1	120.6 (2)	C17—C18—H18	119.4
C1—C2—C3	122.0 (3)	C13—C18—H18	119.4
C1—C2—H2	119.0	N2—C19—C20	121.9 (3)
C3—C2—H2	119.0	N2—C19—C19^i	116.05 (19)
C2—C3—C4	118.9 (3)	C20—C19—C19^i	122.0 (2)
C2—C3—H3	120.6	C19—C20—C21	119.4 (3)
C4—C3—H3	120.5	C19—C20—H20	120.3
C5—C4—C3	120.2 (3)	C21—C20—H20	120.3
C5—C4—H4	119.9	C22—C21—C20	118.5 (3)
C3—C4—H4	119.9	C22—C21—H21	120.8
C4—C5—C6	120.1 (3)	C20—C21—H21	120.8
C4—C5—H5	119.9	C23—C22—C21	118.0 (3)
C6—C5—H5	119.9	C23—C22—H22	121.0
C5—C6—C1	120.7 (3)	C21—C22—H22	121.0
C5—C6—H6	119.6	N2—C23—C22	124.5 (3)
C1—C6—H6	119.6	N2—C23—H23	117.7
C12—C7—C8	118.5 (3)	C22—C23—H23	117.7
C12—C7—Sn1	119.7 (2)	N1—C24—C25	122.4 (3)
C8—C7—Sn1	121.8 (2)	N1—C24—C24^i	115.89 (18)
C9—C8—C7	120.5 (3)	C25—C24—C24^i	121.7 (2)
C9—C8—H8	119.8	C26—C25—C24	119.3 (3)
C7—C8—H8	119.8	C26—C25—H25	120.4
C8—C9—C10	120.9 (3)	C24—C25—H25	120.4
C8—C9—H9	119.5	C27—C26—C25	118.5 (3)
C10—C9—H9	119.5	C27—C26—H26	120.8
C9—C10—C11	119.2 (3)	C25—C26—H26	120.8
C9—C10—H10	120.4	C28—C27—C26	118.4 (3)
C11—C10—H10	120.4	C28—C27—H27	120.8
C10—C11—C12	120.0 (3)	C26—C27—H27	120.8
C10—C11—H11A	120.0	N1—C28—C27	124.1 (3)
C12—C11—H11A	120.0	N1—C28—H28	118.0
C7—C12—C11	120.9 (3)	C27—C28—H28	118.0
C7—C12—H12A	119.6
C7—Sn1—C1—C2	−32.3 (3)	C7—Sn1—C13—C18	95.2 (2)
C13—Sn1—C1—C2	159.3 (2)	C1—Sn1—C13—C18	−95.3 (2)
O1W—Sn1—C1—C2	−112.6 (2)	O1W—Sn1—C13—C18	179.8 (2)
Cl1—Sn1—C1—C2	61.1 (2)	Cl1—Sn1—C13—C18	−0.6 (2)
C7—Sn1—C1—C6	152.1 (2)	C7—Sn1—C13—C14	−83.8 (2)
C13—Sn1—C1—C6	−16.3 (3)	C1—Sn1—C13—C14	85.7 (2)
O1W—Sn1—C1—C6	71.8 (2)	O1W—Sn1—C13—C14	0.7 (2)
Cl1—Sn1—C1—C6	−114.5 (2)	Cl1—Sn1—C13—C14	−179.6 (2)
C6—C1—C2—C3	0.4 (5)	C18—C13—C14—C15	−0.8 (4)
Sn1—C1—C2—C3	−175.3 (2)	Sn1—C13—C14—C15	178.3 (2)
C1—C2—C3—C4	−1.0 (5)	C13—C14—C15—C16	1.3 (5)
C2—C3—C4—C5	0.7 (5)	C14—C15—C16—C17	−1.4 (5)
C3—C4—C5—C6	0.2 (5)	C15—C16—C17—C18	1.1 (5)
C4—C5—C6—C1	−0.8 (5)	C16—C17—C18—C13	−0.5 (5)
C2—C1—C6—C5	0.5 (4)	C14—C13—C18—C17	0.4 (4)
Sn1—C1—C6—C5	176.2 (2)	Sn1—C13—C18—C17	−178.7 (2)
C1—Sn1—C7—C12	−164.2 (2)	C23—N2—C19—C20	0.4 (4)
C13—Sn1—C7—C12	4.5 (3)	C23—N2—C19—C19^i	−178.9 (3)
O1W—Sn1—C7—C12	−83.7 (2)	N2—C19—C20—C21	−1.6 (4)
Cl1—Sn1—C7—C12	103.2 (2)	C19^i—C19—C20—C21	177.7 (3)
C1—Sn1—C7—C8	15.0 (3)	C19—C20—C21—C22	0.6 (4)
C13—Sn1—C7—C8	−176.3 (2)	C20—C21—C22—C23	1.5 (4)
O1W—Sn1—C7—C8	95.5 (2)	C19—N2—C23—C22	1.9 (4)
Cl1—Sn1—C7—C8	−77.6 (2)	C21—C22—C23—N2	−2.9 (5)
C12—C7—C8—C9	0.3 (5)	C28—N1—C24—C25	0.4 (4)
Sn1—C7—C8—C9	−178.9 (2)	C28—N1—C24—C24^i	−179.6 (3)
C7—C8—C9—C10	−0.9 (5)	N1—C24—C25—C26	0.0 (5)
C8—C9—C10—C11	0.8 (5)	C24^i—C24—C25—C26	180.0 (3)
C9—C10—C11—C12	−0.1 (5)	C24—C25—C26—C27	−0.4 (5)
C8—C7—C12—C11	0.4 (5)	C25—C26—C27—C28	0.5 (5)
Sn1—C7—C12—C11	179.7 (2)	C24—N1—C28—C27	−0.4 (5)
C10—C11—C12—C7	−0.5 (5)	C26—C27—C28—N1	−0.1 (5)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···N1	0.84 (1)	1.96 (1)	2.784 (3)	169 (4)
O1W—H12···N2	0.83 (1)	1.94 (1)	2.773 (3)	177 (4)

(Pb1) (3-Amino-1,3-dimethylurea)dinitratolead(II)

Crystal data

Pb(NO3)2(C3H9N3S)	F(000) = 832
Mr = 450.40	Dx = 2.865 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4716 reflections
a = 5.3641 (2) Å	θ = 3.9–27.5°
b = 13.8966 (6) Å	µ = 16.38 mm^−1
c = 14.2315 (6) Å	T = 100 K
β = 100.132 (4)°	Prism, colorless
V = 1044.31 (7) Å^3	0.61 × 0.28 × 0.10 mm
Z = 4

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	2366 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2129 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.048
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 3.3°
ω scan	h = −6→6
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −14→17
Tmin = 0.026, Tmax = 0.259	l = −18→17
8462 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.070	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0346P)^2] where P = (Fo^2 + 2Fc^2)/3
2366 reflections	(Δ/σ)max = 0.001
147 parameters	Δρmax = 0.93 e Å^−3
0 restraints	Δρmin = −3.54 e Å^−3

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

	x	y	z	Uiso*/Ueq
Pb1	0.20589 (3)	0.833612 (14)	0.541141 (13)	0.00811 (9)
S1	0.2992 (2)	0.65917 (10)	0.46598 (9)	0.0118 (3)
O1	0.4545 (7)	0.9101 (3)	0.4219 (3)	0.0161 (8)
O2	0.1053 (7)	0.9904 (3)	0.4126 (3)	0.0142 (8)
O3	0.3941 (7)	1.0384 (3)	0.3333 (3)	0.0153 (8)
O4	−0.2663 (6)	0.7812 (3)	0.5693 (3)	0.0110 (8)
O5	−0.0115 (7)	0.7554 (3)	0.7024 (3)	0.0161 (9)
O6	−0.4181 (7)	0.7416 (3)	0.6953 (3)	0.0159 (9)
N1	−0.0887 (8)	0.8011 (3)	0.3852 (3)	0.0103 (9)
H11	−0.2273	0.8353	0.3840	0.012*
H12	−0.0154	0.8214	0.3382	0.012*
N2	−0.1586 (8)	0.7040 (3)	0.3680 (3)	0.0090 (9)
H2	−0.3122	0.6894	0.3385	0.011*
N3	−0.0568 (8)	0.5448 (3)	0.3701 (3)	0.0102 (9)
N4	0.3177 (8)	0.9817 (3)	0.3882 (3)	0.0113 (9)
N5	−0.2328 (8)	0.7593 (3)	0.6573 (3)	0.0097 (9)
C1	0.0113 (9)	0.6335 (4)	0.3969 (4)	0.0082 (10)
C2	−0.2984 (10)	0.5235 (4)	0.3087 (4)	0.0163 (12)
H2A	−0.2927	0.5446	0.2434	0.024*
H2B	−0.4349	0.5574	0.3325	0.024*
H2C	−0.3299	0.4540	0.3090	0.024*
C3	0.1166 (10)	0.4629 (4)	0.3891 (4)	0.0121 (11)
H3A	0.2583	0.4799	0.4397	0.018*
H3B	0.1813	0.4464	0.3309	0.018*
H3C	0.0260	0.4075	0.4094	0.018*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pb1	0.00866 (13)	0.00781 (14)	0.00793 (13)	−0.00084 (7)	0.00165 (9)	−0.00065 (7)
S1	0.0105 (7)	0.0102 (8)	0.0134 (7)	0.0013 (5)	−0.0016 (6)	−0.0023 (5)
O1	0.0161 (19)	0.013 (2)	0.020 (2)	0.0062 (16)	0.0057 (16)	0.0035 (17)
O2	0.0106 (19)	0.015 (2)	0.019 (2)	0.0045 (15)	0.0066 (16)	0.0024 (16)
O3	0.022 (2)	0.013 (2)	0.0135 (19)	−0.0023 (16)	0.0099 (17)	0.0061 (16)
O4	0.0107 (18)	0.015 (2)	0.0059 (17)	−0.0021 (15)	−0.0018 (14)	0.0006 (16)
O5	0.0083 (17)	0.022 (3)	0.014 (2)	0.0016 (15)	−0.0076 (15)	−0.0008 (17)
O6	0.015 (2)	0.019 (2)	0.017 (2)	0.0016 (17)	0.0108 (17)	0.0011 (17)
N1	0.010 (2)	0.009 (2)	0.013 (2)	0.0004 (18)	0.0032 (18)	−0.0015 (19)
N2	0.006 (2)	0.007 (2)	0.013 (2)	−0.0013 (17)	0.0009 (18)	−0.0030 (19)
N3	0.011 (2)	0.007 (2)	0.013 (2)	−0.0013 (17)	0.0019 (18)	−0.0038 (18)
N4	0.012 (2)	0.010 (2)	0.010 (2)	−0.0026 (18)	0.0000 (18)	−0.0065 (18)
N5	0.013 (2)	0.006 (2)	0.009 (2)	0.0013 (17)	0.0000 (19)	0.0003 (17)
C1	0.008 (2)	0.010 (3)	0.007 (2)	0.000 (2)	0.004 (2)	0.000 (2)
C2	0.016 (3)	0.017 (3)	0.016 (3)	−0.005 (2)	0.001 (2)	−0.006 (2)
C3	0.016 (3)	0.006 (3)	0.015 (3)	0.001 (2)	0.002 (2)	−0.003 (2)

Geometric parameters (Å, º)

Pb1—N1	2.529 (4)	O6—N5	1.237 (5)
Pb1—O1	2.566 (4)	N1—N2	1.409 (6)
Pb1—S1	2.7311 (14)	N1—H11	0.8800
Pb1—O4	2.732 (3)	N1—H12	0.8800
Pb1—O2	2.836 (4)	N2—C1	1.353 (7)
Pb1—O4^i	2.882 (3)	N2—H2	0.8800
Pb1—O5	2.958 (4)	N3—C1	1.322 (7)
Pb1—O6^i	2.993 (4)	N3—C2	1.461 (7)
Pb1—O3^ii	3.100 (4)	N3—C3	1.465 (7)
Pb1—O2^iii	3.096 (4)	C2—H2A	0.9800
S1—C1	1.716 (5)	C2—H2B	0.9800
O1—N4	1.279 (6)	C2—H2C	0.9800
O2—N4	1.253 (6)	C3—H3A	0.9800
O3—N4	1.230 (6)	C3—H3B	0.9800
O4—N5	1.271 (5)	C3—H3C	0.9800
O5—N5	1.247 (5)
N1—Pb1—O1	79.09 (14)	O5—Pb1—O2^iii	79.87 (10)
N1—Pb1—S1	68.08 (11)	O6^i—Pb1—O2^iii	120.02 (10)
O1—Pb1—S1	87.49 (9)	O3^ii—Pb1—O2^iii	76.63 (10)
N1—Pb1—O4	68.19 (13)	C1—S1—Pb1	101.59 (19)
O1—Pb1—O4	144.14 (12)	N4—O1—Pb1	103.8 (3)
S1—Pb1—O4	93.39 (9)	N4—O2—Pb1	91.4 (3)
N1—Pb1—O2	63.42 (14)	N5—O4—Pb1	103.6 (3)
O1—Pb1—O2	46.91 (11)	N5—O5—Pb1	93.1 (3)
S1—Pb1—O2	117.16 (8)	N2—N1—Pb1	115.5 (3)
O4—Pb1—O2	102.92 (11)	N2—N1—H11	108.4
N1—Pb1—O4^i	121.58 (12)	Pb1—N1—H11	108.4
O1—Pb1—O4^i	65.46 (11)	N2—N1—H12	108.4
S1—Pb1—O4^i	65.60 (8)	Pb1—N1—H12	108.4
O4—Pb1—O4^i	145.64 (15)	H11—N1—H12	107.5
O2—Pb1—O4^i	110.77 (11)	C1—N2—N1	119.7 (4)
N1—Pb1—O5	110.14 (12)	C1—N2—H2	120.1
O1—Pb1—O5	170.76 (12)	N1—N2—H2	120.1
S1—Pb1—O5	95.86 (8)	C1—N3—C2	122.2 (5)
O4—Pb1—O5	44.44 (10)	C1—N3—C3	122.5 (5)
O2—Pb1—O5	136.63 (10)	C2—N3—C3	114.8 (4)
O4^i—Pb1—O5	108.12 (10)	O3—N4—O2	122.3 (5)
N1—Pb1—O6^i	143.46 (13)	O3—N4—O1	120.2 (4)
O1—Pb1—O6^i	107.47 (11)	O2—N4—O1	117.5 (4)
S1—Pb1—O6^i	76.21 (8)	O6—N5—O5	122.1 (4)
O4—Pb1—O6^i	107.53 (10)	O6—N5—O4	119.5 (4)
O2—Pb1—O6^i	145.94 (11)	O5—N5—O4	118.3 (4)
O4^i—Pb1—O6^i	43.23 (10)	N3—C1—N2	116.8 (5)
O5—Pb1—O6^i	65.24 (10)	N3—C1—S1	122.3 (4)
N1—Pb1—O3^ii	150.56 (13)	N2—C1—S1	120.9 (4)
O1—Pb1—O3^ii	75.89 (11)	N3—C2—H2A	109.5
S1—Pb1—O3^ii	125.38 (8)	N3—C2—H2B	109.5
O4—Pb1—O3^ii	129.35 (10)	H2A—C2—H2B	109.5
O2—Pb1—O3^ii	87.99 (11)	N3—C2—H2C	109.5
O4^i—Pb1—O3^ii	60.10 (11)	H2A—C2—H2C	109.5
O5—Pb1—O3^ii	95.22 (10)	H2B—C2—H2C	109.5
O6^i—Pb1—O3^ii	60.90 (11)	N3—C3—H3A	109.5
N1—Pb1—O2^iii	92.92 (13)	N3—C3—H3B	109.5
O1—Pb1—O2^iii	100.14 (11)	H3A—C3—H3B	109.5
S1—Pb1—O2^iii	157.98 (8)	N3—C3—H3C	109.5
O4—Pb1—O2^iii	68.34 (11)	H3A—C3—H3C	109.5
O2—Pb1—O2^iii	58.80 (12)	H3B—C3—H3C	109.5
O4^i—Pb1—O2^iii	136.32 (11)
N1—Pb1—S1—C1	−24.7 (2)	N1—Pb1—O5—N5	−24.4 (3)
O1—Pb1—S1—C1	−103.9 (2)	S1—Pb1—O5—N5	−93.2 (3)
O4—Pb1—S1—C1	40.17 (19)	O4—Pb1—O5—N5	−4.3 (3)
O2—Pb1—S1—C1	−66.2 (2)	O2—Pb1—O5—N5	47.8 (3)
O4^i—Pb1—S1—C1	−168.0 (2)	O4^i—Pb1—O5—N5	−159.4 (3)
O5—Pb1—S1—C1	84.70 (19)	O6^i—Pb1—O5—N5	−165.1 (3)
O6^i—Pb1—S1—C1	147.40 (19)	O3^ii—Pb1—O5—N5	140.4 (3)
O3^ii—Pb1—S1—C1	−174.63 (19)	O2^iii—Pb1—O5—N5	65.0 (3)
O2^iii—Pb1—S1—C1	7.3 (3)	O1—Pb1—N1—N2	125.6 (3)
N1—Pb1—O1—N4	67.0 (3)	S1—Pb1—N1—N2	33.9 (3)
S1—Pb1—O1—N4	135.1 (3)	O4—Pb1—N1—N2	−69.4 (3)
O4—Pb1—O1—N4	42.8 (4)	O2—Pb1—N1—N2	172.6 (4)
O2—Pb1—O1—N4	3.3 (3)	O4^i—Pb1—N1—N2	73.5 (3)
O4^i—Pb1—O1—N4	−160.6 (3)	O5—Pb1—N1—N2	−54.4 (3)
O6^i—Pb1—O1—N4	−150.2 (3)	O6^i—Pb1—N1—N2	20.9 (4)
O3^ii—Pb1—O1—N4	−97.4 (3)	O3^ii—Pb1—N1—N2	157.7 (3)
O2^iii—Pb1—O1—N4	−24.1 (3)	O2^iii—Pb1—N1—N2	−134.7 (3)
N1—Pb1—O2—N4	−103.6 (3)	Pb1—N1—N2—C1	−36.0 (5)
O1—Pb1—O2—N4	−3.3 (3)	Pb1—O2—N4—O3	−175.4 (4)
S1—Pb1—O2—N4	−60.1 (3)	Pb1—O2—N4—O1	5.4 (4)
O4—Pb1—O2—N4	−160.8 (3)	Pb1—O1—N4—O3	174.6 (4)
O4^i—Pb1—O2—N4	12.3 (3)	Pb1—O1—N4—O2	−6.2 (5)
O5—Pb1—O2—N4	164.7 (2)	Pb1—O5—N5—O6	−173.5 (4)
O6^i—Pb1—O2—N4	46.2 (4)	Pb1—O5—N5—O4	7.4 (5)
O3^ii—Pb1—O2—N4	69.2 (3)	Pb1—O4—N5—O6	172.6 (4)
O2^iii—Pb1—O2—N4	144.8 (4)	Pb1—O4—N5—O5	−8.3 (5)
N1—Pb1—O4—N5	164.0 (3)	C2—N3—C1—N2	2.7 (7)
O1—Pb1—O4—N5	−170.3 (3)	C3—N3—C1—N2	174.4 (4)
S1—Pb1—O4—N5	99.3 (3)	C2—N3—C1—S1	−178.0 (4)
O2—Pb1—O4—N5	−141.9 (3)	C3—N3—C1—S1	−6.2 (7)
O4^i—Pb1—O4—N5	49.6 (5)	N1—N2—C1—N3	−173.3 (4)
O5—Pb1—O4—N5	4.4 (3)	N1—N2—C1—S1	7.4 (6)
O6^i—Pb1—O4—N5	22.7 (3)	Pb1—S1—C1—N3	−158.9 (4)
O3^ii—Pb1—O4—N5	−43.7 (3)	Pb1—S1—C1—N2	20.4 (4)
O2^iii—Pb1—O4—N5	−93.4 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O1^iv	0.88	2.15	3.004 (6)	164
N1—H12···O6^v	0.88	2.36	3.060 (6)	137
N2—H2···O5^vi	0.88	2.18	2.808 (6)	128

Symmetry codes: (iv) x−1, y, z; (v) x+1/2, −y+3/2, z−1/2; (vi) x−1/2, −y+3/2, z−1/2.

(Pb2) (3-Amino-1,3-dimethylurea)dinitratolead(II)

Crystal data

Pb(NO3)2(C3H9N3S)	F(000) = 832
Mr = 450.40	Dx = 2.889 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5411 reflections
a = 5.3460 (2) Å	θ = 3.3–27.5°
b = 13.8593 (5) Å	µ = 16.52 mm^−1
c = 14.1995 (6) Å	T = 100 K
β = 100.138 (4)°	Prism, colorless
V = 1035.64 (7) Å^3	0.34 × 0.26 × 0.09 mm
Z = 4

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	2384 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2144 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.062
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 3.3°
ω scan	h = −6→6
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −17→18
Tmin = 0.034, Tmax = 0.282	l = −18→17
9294 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) = 0.065	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0272P)^2] where P = (Fo^2 + 2Fc^2)/3
2384 reflections	(Δ/σ)max = 0.001
147 parameters	Δρmax = 1.13 e Å^−3
0 restraints	Δρmin = −2.27 e Å^−3

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

	x	y	z	Uiso*/Ueq
Pb1	0.20583 (3)	0.833646 (12)	0.541136 (13)	0.00659 (8)
S1	0.2992 (2)	0.65909 (9)	0.46613 (10)	0.0097 (3)
O1	0.4546 (6)	0.9104 (3)	0.4222 (3)	0.0126 (8)
O2	0.1055 (7)	0.9909 (2)	0.4125 (3)	0.0121 (8)
O3	0.3935 (7)	1.0387 (3)	0.3328 (3)	0.0151 (8)
O4	−0.2670 (6)	0.7815 (3)	0.5696 (3)	0.0102 (7)
O5	−0.0106 (7)	0.7547 (3)	0.7029 (3)	0.0145 (8)
O6	−0.4187 (7)	0.7418 (3)	0.6956 (3)	0.0141 (8)
N1	−0.0895 (8)	0.8011 (3)	0.3852 (3)	0.0081 (9)
H11	−0.2289	0.8351	0.3842	0.010*
H12	−0.0165	0.8219	0.3381	0.010*
N2	−0.1584 (8)	0.7040 (3)	0.3675 (3)	0.0093 (9)
H2	−0.3122	0.6894	0.3376	0.011*
N3	−0.0570 (8)	0.5441 (3)	0.3702 (3)	0.0098 (9)
N4	0.3170 (8)	0.9815 (3)	0.3885 (3)	0.0095 (9)
N5	−0.2331 (8)	0.7594 (3)	0.6575 (3)	0.0095 (9)
C1	0.0112 (9)	0.6334 (4)	0.3965 (4)	0.0084 (10)
C2	−0.2994 (10)	0.5239 (4)	0.3087 (4)	0.0137 (11)
H2A	−0.2935	0.5459	0.2436	0.021*
H2B	−0.4355	0.5580	0.3332	0.021*
H2C	−0.3324	0.4544	0.3081	0.021*
C3	0.1164 (10)	0.4626 (3)	0.3888 (4)	0.0112 (11)
H3A	0.2619	0.4805	0.4378	0.017*
H3B	0.1761	0.4448	0.3298	0.017*
H3C	0.0278	0.4076	0.4114	0.017*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pb1	0.00688 (12)	0.00441 (11)	0.00843 (13)	−0.00091 (6)	0.00118 (8)	−0.00066 (6)
S1	0.0070 (6)	0.0066 (6)	0.0143 (8)	0.0011 (4)	−0.0011 (5)	−0.0016 (5)
O1	0.0105 (18)	0.0122 (18)	0.016 (2)	0.0045 (14)	0.0050 (15)	0.0044 (15)
O2	0.0081 (17)	0.0104 (18)	0.018 (2)	0.0009 (14)	0.0037 (15)	0.0044 (16)
O3	0.023 (2)	0.0120 (18)	0.012 (2)	−0.0025 (16)	0.0065 (16)	0.0062 (16)
O4	0.0092 (17)	0.0151 (19)	0.0050 (18)	−0.0026 (14)	−0.0023 (14)	0.0014 (16)
O5	0.0089 (18)	0.017 (2)	0.014 (2)	0.0024 (14)	−0.0057 (15)	−0.0011 (17)
O6	0.0118 (18)	0.017 (2)	0.015 (2)	0.0008 (15)	0.0073 (16)	0.0034 (16)
N1	0.010 (2)	0.0020 (18)	0.012 (2)	−0.0018 (17)	0.0017 (17)	−0.0014 (18)
N2	0.006 (2)	0.005 (2)	0.017 (2)	−0.0017 (16)	0.0007 (17)	0.0023 (18)
N3	0.009 (2)	0.008 (2)	0.012 (2)	−0.0008 (17)	0.0012 (17)	0.0017 (18)
N4	0.012 (2)	0.008 (2)	0.007 (2)	−0.0001 (17)	−0.0010 (17)	−0.0013 (17)
N5	0.010 (2)	0.0018 (18)	0.016 (2)	−0.0013 (16)	0.0004 (18)	−0.0017 (17)
C1	0.007 (2)	0.008 (2)	0.011 (3)	0.002 (2)	0.0027 (19)	0.004 (2)
C2	0.008 (2)	0.014 (3)	0.018 (3)	−0.005 (2)	0.000 (2)	−0.004 (2)
C3	0.015 (3)	0.004 (2)	0.015 (3)	−0.002 (2)	0.003 (2)	0.001 (2)

Geometric parameters (Å, º)

Pb1—N1	2.524 (4)	O6—N5	1.235 (5)
Pb1—O1	2.558 (4)	N1—N2	1.405 (6)
Pb1—S1	2.7245 (12)	N1—H11	0.8800
Pb1—O4	2.727 (3)	N1—H12	0.8800
Pb1—O2	2.833 (4)	N2—C1	1.348 (7)
Pb1—O4^i	2.868 (3)	N2—H2	0.8800
Pb1—O5	2.957 (4)	N3—C1	1.325 (6)
Pb1—O6^i	2.985 (4)	N3—C2	1.457 (6)
Pb1—O2^ii	3.083 (3)	N3—C3	1.455 (7)
Pb1—O3^iii	3.094 (4)	C2—H2A	0.9800
S1—C1	1.714 (5)	C2—H2B	0.9800
O1—N4	1.271 (5)	C2—H2C	0.9800
O2—N4	1.244 (5)	C3—H3A	0.9800
O3—N4	1.239 (5)	C3—H3B	0.9800
O4—N5	1.267 (6)	C3—H3C	0.9800
O5—N5	1.251 (5)
N1—Pb1—O1	79.21 (13)	O5—Pb1—O3^iii	95.05 (10)
N1—Pb1—S1	68.13 (10)	O6^i—Pb1—O3^iii	60.76 (10)
O1—Pb1—S1	87.66 (8)	O2^ii—Pb1—O3^iii	76.71 (10)
N1—Pb1—O4	68.25 (13)	C1—S1—Pb1	101.67 (18)
O1—Pb1—O4	144.22 (11)	N4—O1—Pb1	103.7 (3)
S1—Pb1—O4	93.48 (8)	N4—O2—Pb1	91.0 (3)
N1—Pb1—O2	63.50 (12)	N5—O4—Pb1	103.5 (3)
O1—Pb1—O2	46.83 (10)	N5—O5—Pb1	92.7 (3)
S1—Pb1—O2	117.25 (8)	N2—N1—Pb1	115.6 (3)
O4—Pb1—O2	102.96 (10)	N2—N1—H11	108.4
N1—Pb1—O4^i	121.73 (12)	Pb1—N1—H11	108.4
O1—Pb1—O4^i	65.53 (10)	N2—N1—H12	108.4
S1—Pb1—O4^i	65.68 (8)	Pb1—N1—H12	108.4
O4—Pb1—O4^i	145.66 (14)	H11—N1—H12	107.5
O2—Pb1—O4^i	110.76 (10)	C1—N2—N1	120.0 (4)
N1—Pb1—O5	110.20 (12)	C1—N2—H2	120.0
O1—Pb1—O5	170.59 (11)	N1—N2—H2	120.0
S1—Pb1—O5	95.65 (7)	C1—N3—C2	121.3 (4)
O4—Pb1—O5	44.54 (10)	C1—N3—C3	122.6 (4)
O2—Pb1—O5	136.86 (10)	C2—N3—C3	115.5 (4)
O4^i—Pb1—O5	107.83 (10)	O3—N4—O2	121.8 (4)
N1—Pb1—O6^i	143.54 (11)	O3—N4—O1	120.1 (4)
O1—Pb1—O6^i	107.59 (11)	O2—N4—O1	118.2 (4)
S1—Pb1—O6^i	76.28 (8)	O6—N5—O5	121.9 (4)
O4—Pb1—O6^i	107.39 (10)	O6—N5—O4	119.5 (4)
O2—Pb1—O6^i	145.92 (10)	O5—N5—O4	118.6 (4)
O4^i—Pb1—O6^i	43.29 (10)	N3—C1—N2	117.1 (5)
O5—Pb1—O6^i	64.90 (10)	N3—C1—S1	122.1 (4)
N1—Pb1—O2^ii	92.90 (12)	N2—C1—S1	120.8 (4)
O1—Pb1—O2^ii	100.12 (10)	N3—C2—H2A	109.5
S1—Pb1—O2^ii	157.95 (7)	N3—C2—H2B	109.5
O4—Pb1—O2^ii	68.17 (10)	H2A—C2—H2B	109.5
O2—Pb1—O2^ii	58.86 (13)	N3—C2—H2C	109.5
O4^i—Pb1—O2^ii	136.29 (10)	H2A—C2—H2C	109.5
O5—Pb1—O2^ii	80.01 (10)	H2B—C2—H2C	109.5
O6^i—Pb1—O2^ii	119.87 (10)	N3—C3—H3A	109.5
N1—Pb1—O3^iii	150.74 (11)	N3—C3—H3B	109.5
O1—Pb1—O3^iii	75.92 (11)	H3A—C3—H3B	109.5
S1—Pb1—O3^iii	125.33 (8)	N3—C3—H3C	109.5
O4—Pb1—O3^iii	129.15 (11)	H3A—C3—H3C	109.5
O2—Pb1—O3^iii	88.06 (10)	H3B—C3—H3C	109.5
O4^i—Pb1—O3^iii	59.99 (10)
N1—Pb1—S1—C1	−24.4 (2)	N1—Pb1—O5—N5	−24.9 (3)
O1—Pb1—S1—C1	−103.7 (2)	S1—Pb1—O5—N5	−93.7 (3)
O4—Pb1—S1—C1	40.45 (19)	O4—Pb1—O5—N5	−4.5 (2)
O2—Pb1—S1—C1	−66.1 (2)	O2—Pb1—O5—N5	47.4 (3)
O4^i—Pb1—S1—C1	−167.9 (2)	O4^i—Pb1—O5—N5	−159.9 (3)
O5—Pb1—S1—C1	85.09 (19)	O6^i—Pb1—O5—N5	−165.6 (3)
O6^i—Pb1—S1—C1	147.51 (19)	O2^ii—Pb1—O5—N5	64.5 (3)
O2^ii—Pb1—S1—C1	7.8 (3)	O3^iii—Pb1—O5—N5	140.0 (3)
O3^iii—Pb1—S1—C1	−174.63 (19)	O1—Pb1—N1—N2	125.3 (3)
N1—Pb1—O1—N4	66.7 (3)	S1—Pb1—N1—N2	33.5 (3)
S1—Pb1—O1—N4	134.8 (3)	O4—Pb1—N1—N2	−69.9 (3)
O4—Pb1—O1—N4	42.1 (4)	O2—Pb1—N1—N2	172.2 (4)
O2—Pb1—O1—N4	3.0 (2)	O4^i—Pb1—N1—N2	73.1 (3)
O4^i—Pb1—O1—N4	−160.9 (3)	O5—Pb1—N1—N2	−54.6 (3)
O6^i—Pb1—O1—N4	−150.4 (3)	O6^i—Pb1—N1—N2	20.2 (4)
O2^ii—Pb1—O1—N4	−24.4 (3)	O2^ii—Pb1—N1—N2	−135.0 (3)
O3^iii—Pb1—O1—N4	−97.8 (3)	O3^iii—Pb1—N1—N2	157.4 (3)
N1—Pb1—O2—N4	−103.4 (3)	Pb1—N1—N2—C1	−35.5 (5)
O1—Pb1—O2—N4	−3.0 (2)	Pb1—O2—N4—O3	−175.7 (4)
S1—Pb1—O2—N4	−59.9 (3)	Pb1—O2—N4—O1	5.0 (4)
O4—Pb1—O2—N4	−160.8 (3)	Pb1—O1—N4—O3	175.0 (4)
O4^i—Pb1—O2—N4	12.6 (3)	Pb1—O1—N4—O2	−5.7 (5)
O5—Pb1—O2—N4	164.7 (2)	Pb1—O5—N5—O6	−173.5 (4)
O6^i—Pb1—O2—N4	46.7 (4)	Pb1—O5—N5—O4	7.7 (4)
O2^ii—Pb1—O2—N4	145.0 (3)	Pb1—O4—N5—O6	172.6 (3)
O3^iii—Pb1—O2—N4	69.4 (3)	Pb1—O4—N5—O5	−8.6 (5)
N1—Pb1—O4—N5	163.8 (3)	C2—N3—C1—N2	3.0 (7)
O1—Pb1—O4—N5	−170.1 (2)	C3—N3—C1—N2	174.0 (5)
S1—Pb1—O4—N5	99.0 (3)	C2—N3—C1—S1	−178.2 (4)
O2—Pb1—O4—N5	−142.0 (3)	C3—N3—C1—S1	−7.2 (7)
O4^i—Pb1—O4—N5	49.0 (4)	N1—N2—C1—N3	−174.0 (5)
O5—Pb1—O4—N5	4.5 (2)	N1—N2—C1—S1	7.1 (7)
O6^i—Pb1—O4—N5	22.3 (3)	Pb1—S1—C1—N3	−158.4 (4)
O2^ii—Pb1—O4—N5	−93.6 (3)	Pb1—S1—C1—N2	20.3 (4)
O3^iii—Pb1—O4—N5	−43.8 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O1^iv	0.88	2.14	2.994 (5)	165
N1—H12···O6^v	0.88	2.35	3.049 (6)	137
N2—H2···O5^vi	0.88	2.16	2.791 (6)	128

Symmetry codes: (iv) x−1, y, z; (v) x+1/2, −y+3/2, z−1/2; (vi) x−1/2, −y+3/2, z−1/2.

(Pb3) (3-Amino-1,3-dimethylurea)dinitratolead(II)

Crystal data

Pb(NO3)2(C3H9N3S)	F(000) = 832
Mr = 450.40	Dx = 2.877 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4958 reflections
a = 5.3522 (2) Å	θ = 4.1–27.5°
b = 13.8783 (6) Å	µ = 16.45 mm^−1
c = 14.2186 (6) Å	T = 100 K
β = 100.048 (4)°	Prism, colorless
V = 1039.95 (7) Å^3	0.25 × 0.22 × 0.09 mm
Z = 4

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	2394 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2110 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.051
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 3.3°
ω scan	h = −6→6
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −18→17
Tmin = 0.062, Tmax = 0.281	l = −14→18
8963 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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.054	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0196P)^2] where P = (Fo^2 + 2Fc^2)/3
2394 reflections	(Δ/σ)max = 0.001
147 parameters	Δρmax = 0.94 e Å^−3
0 restraints	Δρmin = −1.48 e Å^−3

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

	x	y	z	Uiso*/Ueq
Pb1	0.20583 (3)	0.833629 (12)	0.541117 (11)	0.00769 (7)
S1	0.29932 (19)	0.65917 (9)	0.46601 (8)	0.0112 (3)
O1	0.4536 (6)	0.9109 (2)	0.4217 (2)	0.0142 (7)
O2	0.1051 (5)	0.9912 (2)	0.4126 (2)	0.0126 (7)
O3	0.3944 (6)	1.0386 (2)	0.3333 (2)	0.0155 (7)
O4	−0.2659 (5)	0.7811 (2)	0.5692 (2)	0.0106 (7)
O5	−0.0112 (6)	0.7552 (2)	0.7023 (2)	0.0158 (8)
O6	−0.4184 (6)	0.7416 (2)	0.6956 (2)	0.0159 (8)
N1	−0.0881 (7)	0.8011 (3)	0.3853 (3)	0.0098 (8)
H11	−0.2271	0.8353	0.3842	0.012*
H12	−0.0146	0.8217	0.3384	0.012*
N2	−0.1578 (7)	0.7038 (3)	0.3678 (3)	0.0102 (8)
H2	−0.3117	0.6894	0.3382	0.012*
N3	−0.0573 (7)	0.5444 (3)	0.3701 (3)	0.0104 (8)
N4	0.3173 (7)	0.9817 (3)	0.3879 (3)	0.0103 (8)
N5	−0.2331 (7)	0.7595 (3)	0.6575 (3)	0.0084 (8)
C1	0.0101 (8)	0.6331 (4)	0.3961 (3)	0.0095 (9)
C2	−0.2988 (8)	0.5235 (4)	0.3082 (3)	0.0146 (11)
H2A	−0.2904	0.5435	0.2428	0.022*
H2B	−0.4352	0.5588	0.3311	0.022*
H2C	−0.3330	0.4542	0.3093	0.022*
C3	0.1174 (8)	0.4629 (3)	0.3888 (4)	0.0132 (10)
H3A	0.2605	0.4805	0.4387	0.020*
H3B	0.1805	0.4461	0.3302	0.020*
H3C	0.0283	0.4075	0.4101	0.020*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pb1	0.00656 (10)	0.00810 (11)	0.00879 (10)	−0.00077 (6)	0.00242 (7)	−0.00071 (6)
S1	0.0078 (6)	0.0110 (7)	0.0138 (6)	0.0008 (4)	−0.0005 (5)	−0.0018 (4)
O1	0.0100 (16)	0.0127 (19)	0.0209 (19)	0.0045 (13)	0.0059 (14)	0.0034 (14)
O2	0.0077 (15)	0.0140 (19)	0.0177 (18)	0.0020 (13)	0.0068 (13)	0.0005 (14)
O3	0.0200 (18)	0.0151 (19)	0.0139 (17)	−0.0041 (14)	0.0103 (15)	0.0031 (15)
O4	0.0098 (16)	0.015 (2)	0.0065 (15)	−0.0034 (13)	0.0006 (13)	0.0003 (14)
O5	0.0095 (16)	0.021 (2)	0.0139 (18)	0.0036 (13)	−0.0055 (14)	−0.0025 (15)
O6	0.0126 (17)	0.020 (2)	0.0179 (18)	0.0011 (14)	0.0086 (15)	0.0026 (15)
N1	0.0081 (18)	0.011 (2)	0.011 (2)	0.0017 (15)	0.0035 (16)	0.0015 (17)
N2	0.0061 (18)	0.010 (2)	0.014 (2)	−0.0015 (15)	0.0009 (16)	−0.0003 (17)
N3	0.0068 (18)	0.010 (2)	0.014 (2)	0.0032 (15)	0.0014 (16)	−0.0014 (17)
N4	0.0129 (19)	0.008 (2)	0.0107 (19)	−0.0026 (15)	0.0046 (16)	−0.0027 (16)
N5	0.0089 (18)	0.007 (2)	0.0096 (19)	−0.0013 (15)	0.0018 (16)	−0.0023 (15)
C1	0.010 (2)	0.010 (3)	0.009 (2)	0.0015 (18)	0.0037 (18)	0.0006 (19)
C2	0.011 (2)	0.014 (3)	0.018 (3)	−0.0063 (18)	0.003 (2)	−0.007 (2)
C3	0.011 (2)	0.006 (2)	0.024 (3)	0.0006 (18)	0.007 (2)	0.000 (2)

Geometric parameters (Å, º)

Pb1—N1	2.524 (4)	O6—N5	1.235 (5)
Pb1—O1	2.565 (3)	N1—N2	1.412 (5)
Pb1—S1	2.7275 (12)	N1—H11	0.8800
Pb1—O4	2.723 (3)	N1—H12	0.8800
Pb1—O2	2.840 (3)	N2—C1	1.344 (6)
Pb1—O4^i	2.880 (3)	N2—H2	0.8800
Pb1—O5	2.952 (3)	N3—C1	1.317 (6)
Pb1—O6^i	2.993 (3)	N3—C2	1.460 (5)
Pb1—O2^ii	3.082 (3)	N3—C3	1.462 (6)
Pb1—O3^iii	3.095 (3)	C2—H2A	0.9800
S1—C1	1.726 (5)	C2—H2B	0.9800
O1—N4	1.267 (5)	C2—H2C	0.9800
O2—N4	1.252 (4)	C3—H3A	0.9800
O3—N4	1.228 (5)	C3—H3B	0.9800
O4—N5	1.274 (5)	C3—H3C	0.9800
O5—N5	1.247 (5)
N1—Pb1—O1	78.98 (11)	O5—Pb1—O3^iii	95.13 (9)
N1—Pb1—S1	68.08 (9)	O6^i—Pb1—O3^iii	60.84 (9)
O1—Pb1—S1	87.75 (8)	O2^ii—Pb1—O3^iii	76.66 (9)
N1—Pb1—O4	68.21 (11)	C1—S1—Pb1	101.79 (16)
O1—Pb1—O4	143.97 (10)	N4—O1—Pb1	104.2 (2)
S1—Pb1—O4	93.32 (8)	N4—O2—Pb1	91.1 (2)
N1—Pb1—O2	63.48 (11)	N5—O4—Pb1	103.7 (2)
O1—Pb1—O2	46.69 (9)	N5—O5—Pb1	93.1 (2)
S1—Pb1—O2	117.29 (7)	N2—N1—Pb1	115.5 (3)
O4—Pb1—O2	102.92 (9)	N2—N1—H11	108.4
N1—Pb1—O4^i	121.54 (11)	Pb1—N1—H11	108.4
O1—Pb1—O4^i	65.73 (9)	N2—N1—H12	108.4
S1—Pb1—O4^i	65.59 (7)	Pb1—N1—H12	108.4
O4—Pb1—O4^i	145.58 (13)	H11—N1—H12	107.5
O2—Pb1—O4^i	110.83 (9)	C1—N2—N1	120.2 (4)
N1—Pb1—O5	110.24 (10)	C1—N2—H2	119.9
O1—Pb1—O5	170.77 (10)	N1—N2—H2	119.9
S1—Pb1—O5	95.76 (7)	C1—N3—C2	121.7 (4)
O4—Pb1—O5	44.53 (9)	C1—N3—C3	122.4 (4)
O2—Pb1—O5	136.66 (8)	C2—N3—C3	115.3 (4)
O4^i—Pb1—O5	107.99 (9)	O3—N4—O2	122.1 (4)
N1—Pb1—O6^i	143.52 (11)	O3—N4—O1	120.2 (4)
O1—Pb1—O6^i	107.77 (9)	O2—N4—O1	117.7 (4)
S1—Pb1—O6^i	76.28 (7)	O6—N5—O5	122.2 (4)
O4—Pb1—O6^i	107.44 (9)	O6—N5—O4	119.8 (4)
O2—Pb1—O6^i	145.93 (9)	O5—N5—O4	118.0 (4)
O4^i—Pb1—O6^i	43.31 (9)	N3—C1—N2	117.5 (4)
O5—Pb1—O6^i	65.04 (9)	N3—C1—S1	122.1 (3)
N1—Pb1—O2^ii	92.94 (11)	N2—C1—S1	120.3 (4)
O1—Pb1—O2^ii	99.92 (9)	N3—C2—H2A	109.5
S1—Pb1—O2^ii	157.94 (6)	N3—C2—H2B	109.5
O4—Pb1—O2^ii	68.34 (9)	H2A—C2—H2B	109.5
O2—Pb1—O2^ii	58.75 (10)	N3—C2—H2C	109.5
O4^i—Pb1—O2^ii	136.38 (9)	H2A—C2—H2C	109.5
O5—Pb1—O2^ii	79.92 (9)	H2B—C2—H2C	109.5
O6^i—Pb1—O2^ii	119.91 (9)	N3—C3—H3A	109.5
N1—Pb1—O3^iii	150.60 (11)	N3—C3—H3B	109.5
O1—Pb1—O3^iii	75.94 (10)	H3A—C3—H3B	109.5
S1—Pb1—O3^iii	125.39 (7)	N3—C3—H3C	109.5
O4—Pb1—O3^iii	129.34 (9)	H3A—C3—H3C	109.5
O2—Pb1—O3^iii	87.98 (9)	H3B—C3—H3C	109.5
O4^i—Pb1—O3^iii	60.13 (9)
N1—Pb1—S1—C1	−24.57 (18)	N1—Pb1—O5—N5	−24.8 (3)
O1—Pb1—S1—C1	−103.60 (17)	S1—Pb1—O5—N5	−93.5 (2)
O4—Pb1—S1—C1	40.34 (17)	O4—Pb1—O5—N5	−4.6 (2)
O2—Pb1—S1—C1	−66.04 (17)	O2—Pb1—O5—N5	47.6 (3)
O4^i—Pb1—S1—C1	−167.88 (18)	O4^i—Pb1—O5—N5	−159.7 (2)
O5—Pb1—S1—C1	84.96 (17)	O6^i—Pb1—O5—N5	−165.4 (3)
O6^i—Pb1—S1—C1	147.49 (17)	O2^ii—Pb1—O5—N5	64.7 (2)
O2^ii—Pb1—S1—C1	7.6 (2)	O3^iii—Pb1—O5—N5	140.1 (2)
O3^iii—Pb1—S1—C1	−174.57 (17)	O1—Pb1—N1—N2	125.7 (3)
N1—Pb1—O1—N4	66.7 (3)	S1—Pb1—N1—N2	33.7 (2)
S1—Pb1—O1—N4	134.8 (3)	O4—Pb1—N1—N2	−69.5 (3)
O4—Pb1—O1—N4	42.2 (4)	O2—Pb1—N1—N2	172.6 (3)
O2—Pb1—O1—N4	2.9 (2)	O4^i—Pb1—N1—N2	73.3 (3)
O4^i—Pb1—O1—N4	−161.1 (3)	O5—Pb1—N1—N2	−54.4 (3)
O6^i—Pb1—O1—N4	−150.4 (3)	O6^i—Pb1—N1—N2	20.6 (4)
O2^ii—Pb1—O1—N4	−24.4 (3)	O2^ii—Pb1—N1—N2	−134.8 (3)
O3^iii—Pb1—O1—N4	−97.9 (3)	O3^iii—Pb1—N1—N2	157.5 (2)
N1—Pb1—O2—N4	−103.0 (3)	Pb1—N1—N2—C1	−35.9 (5)
O1—Pb1—O2—N4	−2.8 (2)	Pb1—O2—N4—O3	−175.0 (4)
S1—Pb1—O2—N4	−59.6 (2)	Pb1—O2—N4—O1	4.7 (4)
O4—Pb1—O2—N4	−160.3 (2)	Pb1—O1—N4—O3	174.3 (3)
O4^i—Pb1—O2—N4	12.8 (3)	Pb1—O1—N4—O2	−5.4 (4)
O5—Pb1—O2—N4	165.0 (2)	Pb1—O5—N5—O6	−173.6 (4)
O6^i—Pb1—O2—N4	47.0 (3)	Pb1—O5—N5—O4	7.9 (4)
O2^ii—Pb1—O2—N4	145.3 (3)	Pb1—O4—N5—O6	172.7 (3)
O3^iii—Pb1—O2—N4	69.7 (2)	Pb1—O4—N5—O5	−8.8 (4)
N1—Pb1—O4—N5	164.3 (3)	C2—N3—C1—N2	3.4 (6)
O1—Pb1—O4—N5	−169.8 (2)	C3—N3—C1—N2	174.1 (4)
S1—Pb1—O4—N5	99.5 (2)	C2—N3—C1—S1	−177.9 (3)
O2—Pb1—O4—N5	−141.5 (3)	C3—N3—C1—S1	−7.2 (6)
O4^i—Pb1—O4—N5	49.9 (4)	N1—N2—C1—N3	−173.8 (4)
O5—Pb1—O4—N5	4.7 (2)	N1—N2—C1—S1	7.5 (6)
O6^i—Pb1—O4—N5	22.8 (3)	Pb1—S1—C1—N3	−158.4 (4)
O2^ii—Pb1—O4—N5	−93.1 (3)	Pb1—S1—C1—N2	20.2 (4)
O3^iii—Pb1—O4—N5	−43.4 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O1^iv	0.88	2.15	3.008 (5)	165
N1—H12···O6^v	0.88	2.35	3.052 (5)	137
N2—H2···O5^vi	0.88	2.18	2.808 (5)	128

Symmetry codes: (iv) x−1, y, z; (v) x+1/2, −y+3/2, z−1/2; (vi) x−1/2, −y+3/2, z−1/2.

(Pb4) (3-Amino-1,3-dimethylurea)dinitratolead(II)

Crystal data

Pb(NO3)2(C3H9N3S)	F(000) = 832
Mr = 450.40	Dx = 2.875 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4481 reflections
a = 5.3522 (2) Å	θ = 4.2–27.6°
b = 13.8826 (6) Å	µ = 16.44 mm^−1
c = 14.2217 (6) Å	T = 100 K
β = 100.075 (4)°	Prism, colorless
V = 1040.41 (7) Å^3	0.32 × 0.08 × 0.06 mm
Z = 4

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	2396 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2092 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.042
Detector resolution: 10.4041 pixels mm^-1	θmax = 27.6°, θmin = 3.3°
ω scan	h = −6→6
Absorption correction: gaussian CrysAlis PRO (Agilent, 2014)	k = −18→17
Tmin = 0.112, Tmax = 0.423	l = −17→18
9106 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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.047	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0171P)^2] where P = (Fo^2 + 2Fc^2)/3
2396 reflections	(Δ/σ)max = 0.001
147 parameters	Δρmax = 1.14 e Å^−3
0 restraints	Δρmin = −0.93 e Å^−3

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

	x	y	z	Uiso*/Ueq
Pb1	0.20584 (3)	0.833604 (12)	0.541148 (10)	0.00870 (6)
S1	0.29889 (18)	0.65930 (8)	0.46594 (7)	0.0115 (2)
O1	0.4545 (5)	0.9104 (2)	0.4221 (2)	0.0161 (7)
O2	0.1056 (5)	0.9909 (2)	0.4125 (2)	0.0142 (7)
O3	0.3936 (6)	1.0387 (2)	0.3327 (2)	0.0166 (7)
O4	−0.2663 (5)	0.7815 (2)	0.5692 (2)	0.0118 (7)
O5	−0.0108 (5)	0.7554 (2)	0.7023 (2)	0.0165 (7)
O6	−0.4194 (5)	0.7415 (2)	0.6956 (2)	0.0161 (7)
N1	−0.0898 (6)	0.8013 (3)	0.3850 (2)	0.0089 (7)
H11	−0.2289	0.8354	0.3839	0.011*
H12	−0.0166	0.8218	0.3379	0.011*
N2	−0.1586 (6)	0.7041 (3)	0.3681 (2)	0.0100 (8)
H2	−0.3126	0.6896	0.3386	0.012*
N3	−0.0561 (6)	0.5444 (3)	0.3699 (3)	0.0112 (8)
N4	0.3167 (6)	0.9816 (3)	0.3879 (2)	0.0112 (8)
N5	−0.2320 (6)	0.7593 (3)	0.6573 (2)	0.0105 (8)
C1	0.0091 (8)	0.6332 (3)	0.3965 (3)	0.0094 (9)
C2	−0.2990 (8)	0.5237 (4)	0.3085 (3)	0.0175 (10)
H2A	−0.2892	0.5409	0.2425	0.026*
H2B	−0.4333	0.5615	0.3300	0.026*
H2C	−0.3374	0.4549	0.3121	0.026*
C3	0.1162 (8)	0.4627 (3)	0.3885 (3)	0.0132 (9)
H3A	0.2619	0.4803	0.4372	0.020*
H3B	0.1754	0.4447	0.3294	0.020*
H3C	0.0271	0.4080	0.4111	0.020*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pb1	0.00848 (9)	0.00986 (10)	0.00772 (9)	−0.00083 (6)	0.00130 (6)	−0.00064 (6)
S1	0.0085 (5)	0.0125 (6)	0.0123 (5)	0.0015 (4)	−0.0014 (4)	−0.0015 (4)
O1	0.0143 (15)	0.0144 (18)	0.0212 (17)	0.0046 (13)	0.0073 (13)	0.0058 (14)
O2	0.0082 (14)	0.0155 (17)	0.0204 (16)	0.0026 (13)	0.0065 (13)	0.0031 (14)
O3	0.0230 (16)	0.0134 (17)	0.0148 (16)	−0.0050 (14)	0.0073 (14)	0.0040 (14)
O4	0.0130 (15)	0.0173 (18)	0.0045 (14)	−0.0011 (13)	−0.0007 (12)	0.0025 (13)
O5	0.0118 (15)	0.0213 (19)	0.0128 (16)	0.0008 (13)	−0.0077 (13)	−0.0011 (14)
O6	0.0152 (15)	0.0191 (19)	0.0156 (16)	−0.0004 (14)	0.0071 (14)	0.0039 (14)
N1	0.0089 (16)	0.0105 (19)	0.0079 (17)	0.0010 (15)	0.0029 (14)	−0.0036 (15)
N2	0.0089 (17)	0.0121 (19)	0.0082 (17)	−0.0022 (15)	−0.0006 (14)	−0.0014 (16)
N3	0.0088 (17)	0.012 (2)	0.0121 (18)	0.0009 (15)	0.0009 (15)	−0.0018 (16)
N4	0.0122 (18)	0.011 (2)	0.0106 (18)	0.0006 (15)	0.0016 (15)	−0.0014 (15)
N5	0.0118 (18)	0.0107 (19)	0.0089 (17)	0.0010 (15)	0.0021 (15)	−0.0015 (15)
C1	0.011 (2)	0.012 (2)	0.0052 (19)	−0.0008 (18)	0.0008 (17)	0.0004 (17)
C2	0.015 (2)	0.020 (3)	0.016 (2)	−0.0047 (19)	−0.0008 (19)	−0.007 (2)
C3	0.017 (2)	0.010 (2)	0.013 (2)	0.0009 (18)	0.0022 (19)	0.0002 (18)

Geometric parameters (Å, º)

Pb1—N1	2.531 (3)	O6—N5	1.247 (4)
Pb1—O1	2.562 (3)	N1—N2	1.408 (5)
Pb1—S1	2.7264 (11)	N1—H11	0.8800
Pb1—O4	2.724 (3)	N1—H12	0.8800
Pb1—O2	2.839 (3)	N2—C1	1.346 (5)
Pb1—O4^i	2.876 (3)	N2—H2	0.8800
Pb1—O5	2.950 (3)	N3—C1	1.318 (5)
Pb1—O6^i	2.990 (3)	N3—C3	1.457 (5)
Pb1—O2^ii	3.088 (3)	N3—C2	1.462 (5)
Pb1—O3^iii	3.100 (3)	C2—H2A	0.9800
S1—C1	1.725 (4)	C2—H2B	0.9800
O1—N4	1.277 (4)	C2—H2C	0.9800
O2—N4	1.246 (4)	C3—H3A	0.9800
O3—N4	1.236 (5)	C3—H3B	0.9800
O4—N5	1.272 (4)	C3—H3C	0.9800
O5—N5	1.245 (4)
N1—Pb1—O1	79.11 (11)	O5—Pb1—O3^iii	94.99 (8)
N1—Pb1—S1	68.14 (8)	O6^i—Pb1—O3^iii	60.83 (8)
O1—Pb1—S1	87.61 (8)	O2^ii—Pb1—O3^iii	76.69 (8)
N1—Pb1—O4	68.16 (10)	C1—S1—Pb1	101.75 (16)
O1—Pb1—O4	144.08 (9)	N4—O1—Pb1	103.9 (2)
S1—Pb1—O4	93.42 (7)	N4—O2—Pb1	91.3 (2)
N1—Pb1—O2	63.40 (10)	N5—O4—Pb1	103.3 (2)
O1—Pb1—O2	46.80 (8)	N5—O5—Pb1	93.0 (2)
S1—Pb1—O2	117.17 (7)	N2—N1—Pb1	115.1 (2)
O4—Pb1—O2	102.89 (8)	N2—N1—H11	108.5
N1—Pb1—O4^i	121.69 (10)	Pb1—N1—H11	108.5
O1—Pb1—O4^i	65.48 (9)	N2—N1—H12	108.5
S1—Pb1—O4^i	65.72 (6)	Pb1—N1—H12	108.5
O4—Pb1—O4^i	145.78 (12)	H11—N1—H12	107.5
O2—Pb1—O4^i	110.68 (8)	C1—N2—N1	120.6 (3)
N1—Pb1—O5	110.24 (10)	C1—N2—H2	119.7
O1—Pb1—O5	170.65 (8)	N1—N2—H2	119.7
S1—Pb1—O5	95.83 (7)	C1—N3—C3	123.3 (3)
O4—Pb1—O5	44.59 (8)	C1—N3—C2	121.2 (4)
O2—Pb1—O5	136.72 (8)	C3—N3—C2	115.1 (3)
O4^i—Pb1—O5	108.04 (8)	O3—N4—O2	122.0 (4)
N1—Pb1—O6^i	143.58 (10)	O3—N4—O1	120.2 (3)
O1—Pb1—O6^i	107.70 (9)	O2—N4—O1	117.8 (3)
S1—Pb1—O6^i	76.31 (7)	O6—N5—O5	122.2 (3)
O4—Pb1—O6^i	107.41 (8)	O6—N5—O4	119.3 (3)
O2—Pb1—O6^i	146.01 (8)	O5—N5—O4	118.5 (4)
O4^i—Pb1—O6^i	43.44 (8)	N3—C1—N2	118.0 (4)
O5—Pb1—O6^i	64.95 (8)	N3—C1—S1	121.8 (3)
N1—Pb1—O2^ii	92.82 (10)	N2—C1—S1	120.2 (3)
O1—Pb1—O2^ii	100.10 (9)	N3—C2—H2A	109.5
S1—Pb1—O2^ii	157.90 (6)	N3—C2—H2B	109.5
O4—Pb1—O2^ii	68.21 (9)	H2A—C2—H2B	109.5
O2—Pb1—O2^ii	58.84 (10)	N3—C2—H2C	109.5
O4^i—Pb1—O2^ii	136.29 (8)	H2A—C2—H2C	109.5
O5—Pb1—O2^ii	79.87 (8)	H2B—C2—H2C	109.5
O6^i—Pb1—O2^ii	119.90 (8)	N3—C3—H3A	109.5
N1—Pb1—O3^iii	150.67 (10)	N3—C3—H3B	109.5
O1—Pb1—O3^iii	75.99 (9)	H3A—C3—H3B	109.5
S1—Pb1—O3^iii	125.40 (6)	N3—C3—H3C	109.5
O4—Pb1—O3^iii	129.22 (9)	H3A—C3—H3C	109.5
O2—Pb1—O3^iii	88.08 (8)	H3B—C3—H3C	109.5
O4^i—Pb1—O3^iii	60.03 (9)
N1—Pb1—S1—C1	−24.76 (17)	N1—Pb1—O5—N5	−24.3 (3)
O1—Pb1—S1—C1	−103.98 (16)	S1—Pb1—O5—N5	−93.1 (2)
O4—Pb1—S1—C1	40.06 (16)	O4—Pb1—O5—N5	−4.2 (2)
O2—Pb1—S1—C1	−66.32 (17)	O2—Pb1—O5—N5	47.9 (3)
O4^i—Pb1—S1—C1	−168.08 (17)	O4^i—Pb1—O5—N5	−159.5 (2)
O5—Pb1—S1—C1	84.73 (16)	O6^i—Pb1—O5—N5	−165.1 (2)
O6^i—Pb1—S1—C1	147.15 (16)	O2^ii—Pb1—O5—N5	65.0 (2)
O2^ii—Pb1—S1—C1	7.3 (2)	O3^iii—Pb1—O5—N5	140.5 (2)
O3^iii—Pb1—S1—C1	−174.90 (17)	O1—Pb1—N1—N2	125.5 (3)
N1—Pb1—O1—N4	66.4 (2)	S1—Pb1—N1—N2	33.7 (2)
S1—Pb1—O1—N4	134.6 (2)	O4—Pb1—N1—N2	−69.6 (3)
O4—Pb1—O1—N4	42.1 (3)	O2—Pb1—N1—N2	172.4 (3)
O2—Pb1—O1—N4	2.8 (2)	O4^i—Pb1—N1—N2	73.5 (3)
O4^i—Pb1—O1—N4	−161.1 (3)	O5—Pb1—N1—N2	−54.5 (3)
O6^i—Pb1—O1—N4	−150.6 (2)	O6^i—Pb1—N1—N2	20.4 (4)
O2^ii—Pb1—O1—N4	−24.6 (2)	O2^ii—Pb1—N1—N2	−134.8 (3)
O3^iii—Pb1—O1—N4	−98.0 (2)	O3^iii—Pb1—N1—N2	157.7 (2)
N1—Pb1—O2—N4	−103.2 (2)	Pb1—N1—N2—C1	−35.9 (5)
O1—Pb1—O2—N4	−2.8 (2)	Pb1—O2—N4—O3	−175.2 (3)
S1—Pb1—O2—N4	−59.7 (2)	Pb1—O2—N4—O1	4.6 (3)
O4—Pb1—O2—N4	−160.4 (2)	Pb1—O1—N4—O3	174.5 (3)
O4^i—Pb1—O2—N4	12.9 (2)	Pb1—O1—N4—O2	−5.3 (4)
O5—Pb1—O2—N4	165.0 (2)	Pb1—O5—N5—O6	−173.4 (3)
O6^i—Pb1—O2—N4	46.9 (3)	Pb1—O5—N5—O4	7.2 (4)
O2^ii—Pb1—O2—N4	145.3 (3)	Pb1—O4—N5—O6	172.6 (3)
O3^iii—Pb1—O2—N4	69.7 (2)	Pb1—O4—N5—O5	−8.0 (4)
N1—Pb1—O4—N5	163.9 (3)	C3—N3—C1—N2	174.2 (4)
O1—Pb1—O4—N5	−170.3 (2)	C2—N3—C1—N2	2.3 (6)
S1—Pb1—O4—N5	99.1 (2)	C3—N3—C1—S1	−6.1 (6)
O2—Pb1—O4—N5	−142.1 (2)	C2—N3—C1—S1	−178.0 (3)
O4^i—Pb1—O4—N5	49.2 (4)	N1—N2—C1—N3	−172.9 (4)
O5—Pb1—O4—N5	4.2 (2)	N1—N2—C1—S1	7.3 (5)
O6^i—Pb1—O4—N5	22.3 (3)	Pb1—S1—C1—N3	−159.1 (3)
O2^ii—Pb1—O4—N5	−93.6 (2)	Pb1—S1—C1—N2	20.6 (4)
O3^iii—Pb1—O4—N5	−43.9 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O1^iv	0.88	2.14	2.995 (5)	164
N1—H12···O6^v	0.88	2.35	3.050 (5)	137
N2—H2···O5^vi	0.88	2.18	2.806 (4)	128

Symmetry codes: (iv) x−1, y, z; (v) x+1/2, −y+3/2, z−1/2; (vi) x−1/2, −y+3/2, z−1/2.