(Di­methyl sulfoxide-κS)­bis­[2′-(3-methyl­thio­phen-2-yl­methyl­ene)­furan-2-carbohydr­azido]­zinc(II)

The title compound, [Zn(C₁₂H₁₀N₂O₂S)₂(C₂H₆OS)], is monomeric with the Zn atom in a five-coordinate environment. The geometry of the polyhedron is distorted trigonal bipyramidal, with angles of the equatorial atoms about the central Zn atom in the range 77.84 (10)–126.66 (12) Å. The O—Zn—O axial bond angle is 173.12 (12)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.052
• wR factor = 0.149
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.98

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.60 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.07 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C13
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C23
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        S3B
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        S3A
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C15
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          4
            O4  -ZN1 -O1  -C5     80.70  0.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          7
            C23 -S3B -O3  -ZN1   104.00  9.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          8
            C24 -S3B -O3  -ZN1   -22.00 11.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         13
            N4  -ZN1 -O3  -S3B   105.00  9.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         14
            N2  -ZN1 -O3  -S3B   -76.00  9.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         15
            O4  -ZN1 -O3  -S3B  -178.00  9.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         16
            O1  -ZN1 -O3  -S3B     4.00  9.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         24
            O1  -ZN1 -O4  -C16    50.90  0.80   1.555   1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      31.10 Deg.
              C23  -S3A  -H23F    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      31.80 Deg.
              C24  -S3A  -H24E    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      30.70 Deg.
              C23  -S3B  -H23B    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      35.40 Deg.
              S3A  -C23  -S3B     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      25.70 Deg.
              H23A -C23  -H23D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      35.30 Deg.
              S3A  -C24  -S3B     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      25.00 Deg.
              H24A -C24  -H24B    1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  24 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  13 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   9 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

(Dimethyl sulfoxide-κS)bis[2'-(3-methylthiophen-2-ylmethylene)furan- 2-carbohydrazido]zinc(II)

Crystal data

[Zn(C12H10N2O2S)2(C2H6OS)]	Z = 2
Mr = 610.02	F(000) = 628
Triclinic, P1	Dx = 1.470 Mg m^−3
a = 10.4060 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.640 (2) Å	Cell parameters from 5500 reflections
c = 13.152 (2) Å	θ = 1.5–26.0°
α = 93.067 (4)°	µ = 1.16 mm^−1
β = 98.772 (4)°	T = 293 K
γ = 105.796 (4)°	Block, yellow
V = 1377.9 (4) Å^3	0.34 × 0.28 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5322 independent reflections
Radiation source: fine-focus sealed tube	4164 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 83.66 pixels mm^-1	θmax = 26.0°, θmin = 1.5°
ω scans	h = −12→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.693, Tmax = 0.892	l = −16→16
10224 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0898P)^2] where P = (Fo^2 + 2Fc^2)/3
5322 reflections	(Δ/σ)max < 0.001
344 parameters	Δρmax = 0.56 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.21612 (4)	0.31041 (3)	0.17871 (3)	0.04759 (16)
S1	0.57587 (11)	0.73894 (9)	0.36371 (7)	0.0614 (3)
S2	−0.24350 (11)	0.07357 (10)	0.29388 (10)	0.0748 (3)
S3A	0.30698 (15)	0.28592 (14)	−0.03581 (10)	0.0804 (6)	0.923 (4)
S3B	0.254 (2)	0.185 (2)	−0.026 (3)	0.121 (11)	0.077 (4)
O1	0.1665 (2)	0.4641 (2)	0.11215 (19)	0.0581 (6)
O2	0.3145 (3)	0.8089 (2)	0.1509 (2)	0.0611 (7)
O3	0.2424 (4)	0.2207 (3)	0.0494 (2)	0.0775 (9)
O4	0.2546 (2)	0.1625 (2)	0.25925 (19)	0.0545 (6)
O5	0.2640 (3)	−0.0574 (3)	0.3475 (3)	0.0886 (10)
N1	0.3594 (3)	0.5867 (2)	0.2225 (2)	0.0485 (7)
N2	0.3690 (3)	0.4667 (3)	0.2509 (2)	0.0476 (7)
N3	0.0278 (3)	0.1196 (3)	0.2715 (2)	0.0512 (7)
N4	0.0368 (3)	0.2328 (3)	0.2247 (2)	0.0481 (7)
C1	0.1199 (4)	0.7072 (4)	0.0504 (3)	0.0611 (10)
H1B	0.0448	0.6418	0.0157	0.073*
C2	0.1455 (5)	0.8436 (4)	0.0447 (3)	0.0717 (11)
H2A	0.0907	0.8858	0.0056	0.086*
C3	0.2617 (5)	0.8992 (4)	0.1057 (3)	0.0670 (11)
H3B	0.3027	0.9893	0.1164	0.080*
C4	0.2244 (3)	0.6900 (3)	0.1152 (3)	0.0488 (8)
C5	0.2520 (3)	0.5717 (3)	0.1520 (3)	0.0465 (8)
C6	0.4681 (3)	0.4682 (3)	0.3227 (3)	0.0492 (8)
H6A	0.4720	0.3865	0.3424	0.059*
C7	0.5727 (4)	0.5771 (3)	0.3761 (3)	0.0517 (8)
C8	0.7174 (5)	0.7928 (4)	0.4550 (3)	0.0766 (13)
H8A	0.7598	0.8810	0.4770	0.092*
C9	0.7611 (4)	0.6960 (5)	0.4914 (3)	0.0720 (12)
H9A	0.8389	0.7095	0.5409	0.086*
C10	0.6800 (4)	0.5712 (4)	0.4490 (3)	0.0589 (9)
C11	0.7105 (5)	0.4482 (5)	0.4782 (4)	0.0813 (13)
H11A	0.6423	0.3742	0.4399	0.122*
H11B	0.7112	0.4426	0.5509	0.122*
H11C	0.7977	0.4482	0.4626	0.122*
C12	0.0558 (5)	−0.1095 (4)	0.3753 (3)	0.0768 (12)
H12A	−0.0327	−0.1079	0.3772	0.092*
C13	0.2389 (7)	−0.1689 (6)	0.3942 (5)	0.114 (2)
H13A	0.3015	−0.2158	0.4106	0.137*
C14	0.1161 (7)	−0.2027 (5)	0.4134 (4)	0.1016 (17)
H14A	0.0764	−0.2749	0.4461	0.122*
C15	0.1477 (4)	−0.0231 (4)	0.3355 (3)	0.0546 (9)
C17	−0.0695 (3)	0.2736 (3)	0.2118 (3)	0.0501 (8)
H17A	−0.0594	0.3524	0.1823	0.060*
C18	−0.2004 (3)	0.2162 (3)	0.2359 (3)	0.0524 (8)
C19	−0.4056 (4)	0.0814 (5)	0.2858 (4)	0.0878 (15)
H19A	−0.4727	0.0198	0.3105	0.105*
C20	−0.4267 (4)	0.1841 (4)	0.2410 (4)	0.0806 (14)
H20A	−0.5103	0.2015	0.2309	0.097*
C21	−0.3113 (4)	0.2640 (4)	0.2101 (3)	0.0635 (10)
C22	−0.3061 (5)	0.3865 (5)	0.1630 (4)	0.0984 (17)
H22A	−0.2165	0.4243	0.1489	0.148*
H22B	−0.3281	0.4469	0.2097	0.148*
H22C	−0.3703	0.3687	0.0996	0.148*
C23	0.4115 (6)	0.1870 (7)	−0.0688 (4)	0.121 (2)
H23A	0.4882	0.2002	−0.0144	0.181*	0.923 (4)
H23B	0.3599	0.0962	−0.0777	0.181*	0.923 (4)
H23C	0.4424	0.2114	−0.1320	0.181*	0.923 (4)
H23D	0.4670	0.1599	−0.0140	0.181*	0.077 (4)
H23E	0.3956	0.1279	−0.1301	0.181*	0.077 (4)
H23F	0.4568	0.2742	−0.0824	0.181*	0.077 (4)
C24	0.1827 (6)	0.2371 (6)	−0.1477 (4)	0.1080 (18)
H24A	0.1146	0.2817	−0.1444	0.162*	0.923 (4)
H24C	0.1418	0.1440	−0.1525	0.162*	0.923 (4)
H24D	0.2239	0.2588	−0.2074	0.162*	0.923 (4)
H24B	0.0933	0.2428	−0.1431	0.162*	0.077 (4)
H24E	0.2392	0.3218	−0.1575	0.162*	0.077 (4)
H24F	0.1780	0.1755	−0.2052	0.162*	0.077 (4)
C16	0.1465 (3)	0.0945 (3)	0.2850 (2)	0.0470 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0349 (2)	0.0439 (2)	0.0623 (3)	0.00863 (16)	0.00945 (17)	0.00098 (16)
S1	0.0620 (6)	0.0520 (5)	0.0608 (6)	0.0036 (4)	0.0060 (4)	0.0031 (4)
S2	0.0550 (6)	0.0645 (6)	0.1086 (9)	0.0129 (5)	0.0302 (6)	0.0153 (5)
S3A	0.0929 (10)	0.0724 (10)	0.0751 (8)	0.0112 (7)	0.0342 (7)	0.0103 (6)
S3B	0.096 (14)	0.066 (13)	0.24 (3)	0.055 (11)	0.077 (17)	0.045 (14)
O1	0.0463 (14)	0.0487 (13)	0.0697 (16)	0.0072 (11)	−0.0072 (12)	0.0048 (11)
O2	0.0566 (16)	0.0466 (13)	0.0733 (16)	0.0133 (11)	−0.0052 (13)	0.0016 (11)
O3	0.104 (3)	0.0652 (18)	0.0727 (19)	0.0245 (17)	0.0459 (18)	−0.0004 (14)
O4	0.0387 (13)	0.0571 (14)	0.0733 (16)	0.0200 (11)	0.0132 (11)	0.0127 (11)
O5	0.083 (2)	0.094 (2)	0.121 (3)	0.0560 (18)	0.0441 (19)	0.0512 (19)
N1	0.0396 (15)	0.0400 (14)	0.0629 (17)	0.0099 (11)	0.0028 (13)	0.0032 (12)
N2	0.0320 (14)	0.0464 (15)	0.0631 (17)	0.0104 (11)	0.0051 (12)	0.0052 (12)
N3	0.0406 (16)	0.0536 (16)	0.0607 (17)	0.0145 (13)	0.0092 (13)	0.0102 (13)
N4	0.0330 (14)	0.0515 (15)	0.0604 (17)	0.0127 (12)	0.0082 (12)	0.0077 (12)
C1	0.054 (2)	0.058 (2)	0.065 (2)	0.0122 (17)	−0.0013 (18)	0.0076 (16)
C2	0.078 (3)	0.062 (2)	0.075 (3)	0.028 (2)	−0.002 (2)	0.0101 (19)
C3	0.076 (3)	0.0440 (19)	0.078 (3)	0.0173 (19)	0.004 (2)	0.0069 (17)
C4	0.0452 (19)	0.0486 (18)	0.0521 (19)	0.0122 (15)	0.0098 (15)	0.0015 (14)
C5	0.0386 (18)	0.0474 (17)	0.0543 (19)	0.0122 (14)	0.0111 (15)	0.0037 (14)
C6	0.0414 (19)	0.0479 (18)	0.061 (2)	0.0167 (14)	0.0095 (16)	0.0061 (14)
C7	0.0436 (19)	0.059 (2)	0.0520 (19)	0.0118 (15)	0.0100 (15)	0.0058 (15)
C8	0.079 (3)	0.066 (3)	0.065 (3)	−0.005 (2)	0.002 (2)	−0.0024 (19)
C9	0.049 (2)	0.097 (3)	0.054 (2)	0.001 (2)	−0.0030 (18)	−0.001 (2)
C10	0.048 (2)	0.080 (3)	0.0489 (19)	0.0166 (18)	0.0122 (16)	0.0081 (17)
C11	0.071 (3)	0.095 (3)	0.081 (3)	0.037 (3)	−0.004 (2)	0.016 (2)
C12	0.064 (3)	0.077 (3)	0.093 (3)	0.020 (2)	0.019 (2)	0.031 (2)
C13	0.130 (5)	0.122 (5)	0.141 (5)	0.087 (4)	0.061 (4)	0.080 (4)
C14	0.108 (4)	0.090 (4)	0.125 (4)	0.038 (3)	0.041 (4)	0.059 (3)
C15	0.055 (2)	0.061 (2)	0.053 (2)	0.0242 (17)	0.0114 (17)	0.0037 (16)
C17	0.0377 (18)	0.0536 (19)	0.060 (2)	0.0142 (15)	0.0104 (15)	0.0052 (15)
C18	0.0381 (18)	0.058 (2)	0.061 (2)	0.0149 (15)	0.0099 (15)	−0.0048 (15)
C19	0.050 (3)	0.082 (3)	0.135 (4)	0.009 (2)	0.043 (3)	0.006 (3)
C20	0.045 (2)	0.074 (3)	0.124 (4)	0.018 (2)	0.025 (2)	−0.020 (3)
C21	0.042 (2)	0.069 (2)	0.082 (3)	0.0203 (18)	0.0156 (18)	−0.0089 (19)
C22	0.074 (3)	0.111 (4)	0.132 (5)	0.057 (3)	0.022 (3)	0.025 (3)
C23	0.091 (4)	0.196 (7)	0.096 (4)	0.071 (4)	0.028 (3)	0.011 (4)
C24	0.092 (4)	0.144 (5)	0.096 (4)	0.041 (4)	0.019 (3)	0.026 (3)
C16	0.0437 (19)	0.0506 (18)	0.0458 (17)	0.0138 (15)	0.0060 (14)	0.0011 (13)

Geometric parameters (Å, º)

Zn1—O3	1.997 (3)	C7—C10	1.374 (5)
Zn1—N4	2.022 (3)	C8—C9	1.319 (7)
Zn1—N2	2.032 (3)	C8—H8A	0.9300
Zn1—O4	2.038 (2)	C9—C10	1.397 (5)
Zn1—O1	2.045 (2)	C9—H9A	0.9300
S1—C8	1.693 (4)	C10—C11	1.485 (6)
S1—C7	1.730 (4)	C11—H11A	0.9600
S2—C19	1.699 (5)	C11—H11B	0.9600
S2—C18	1.716 (4)	C11—H11C	0.9600
S3A—O3	1.500 (3)	C12—C15	1.326 (5)
S3A—C24	1.755 (6)	C12—C14	1.387 (7)
S3A—C23	1.788 (6)	C12—H12A	0.9300
S3A—H23F	1.7921	C13—C14	1.297 (8)
S3A—H24E	1.7527	C13—H13A	0.9300
S3B—O3	1.07 (3)	C14—H14A	0.9300
S3B—C23	1.81 (2)	C15—C16	1.451 (5)
S3B—C24	1.84 (3)	C17—C18	1.425 (5)
S3B—H23B	1.8186	C17—H17A	0.9300
O1—C5	1.271 (4)	C18—C21	1.387 (5)
O2—C3	1.352 (5)	C19—C20	1.322 (7)
O2—C4	1.362 (4)	C19—H19A	0.9300
O4—C16	1.266 (4)	C20—C21	1.399 (6)
O5—C13	1.346 (6)	C20—H20A	0.9300
O5—C15	1.346 (5)	C21—C22	1.465 (6)
N1—C5	1.306 (4)	C22—H22A	0.9600
N1—N2	1.374 (4)	C22—H22B	0.9600
N2—C6	1.283 (4)	C22—H22C	0.9600
N3—C16	1.321 (4)	C23—H23A	0.9600
N3—N4	1.370 (4)	C23—H23B	0.9600
N4—C17	1.285 (4)	C23—H23C	0.9599
C1—C4	1.335 (5)	C23—H23D	0.9600
C1—C2	1.411 (5)	C23—H23E	0.9600
C1—H1B	0.9300	C23—H23F	0.9599
C2—C3	1.311 (6)	C24—H24A	0.9600
C2—H2A	0.9300	C24—H24C	0.9600
C3—H3B	0.9300	C24—H24D	0.9600
C4—C5	1.457 (5)	C24—H24B	0.9601
C6—C7	1.419 (5)	C24—H24E	0.9600
C6—H6A	0.9300	C24—H24F	0.9599
O3—Zn1—N4	115.33 (12)	C13—C14—H14A	126.8
O3—Zn1—N2	118.01 (13)	C12—C14—H14A	126.8
N4—Zn1—N2	126.66 (12)	C12—C15—O5	109.3 (4)
O3—Zn1—O4	89.96 (12)	C12—C15—C16	133.6 (4)
N4—Zn1—O4	78.15 (10)	O5—C15—C16	117.2 (3)
N2—Zn1—O4	101.19 (10)	N4—C17—C18	129.8 (3)
O3—Zn1—O1	96.51 (12)	N4—C17—H17A	115.1
N4—Zn1—O1	96.89 (11)	C18—C17—H17A	115.1
N2—Zn1—O1	77.84 (10)	C21—C18—C17	124.4 (4)
O4—Zn1—O1	173.12 (10)	C21—C18—S2	111.3 (3)
C8—S1—C7	91.4 (2)	C17—C18—S2	124.2 (3)
C19—S2—C18	90.8 (2)	C20—C19—S2	113.2 (3)
O3—S3A—C24	105.7 (3)	C20—C19—H19A	123.4
O3—S3A—C23	104.2 (3)	S2—C19—H19A	123.4
C24—S3A—C23	96.8 (3)	C19—C20—C21	113.7 (4)
O3—S3A—H23F	129.8	C19—C20—H20A	123.1
C24—S3A—H23F	102.3	C21—C20—H20A	123.1
C23—S3A—H23F	31.1	C18—C21—C20	111.0 (4)
O3—S3A—H24E	132.5	C18—C21—C22	124.4 (4)
C24—S3A—H24E	31.8	C20—C21—C22	124.5 (4)
C23—S3A—H24E	102.0	C21—C22—H22A	109.5
H23F—S3A—H24E	90.7	C21—C22—H22B	109.5
O3—S3B—C23	127 (2)	H22A—C22—H22B	109.5
O3—S3B—C24	123.9 (13)	C21—C22—H22C	109.5
C23—S3B—C24	93.0 (14)	H22A—C22—H22C	109.5
O3—S3B—H23B	136.9	H22B—C22—H22C	109.5
C23—S3B—H23B	30.7	S3A—C23—S3B	35.4 (6)
C24—S3B—H23B	98.0	S3A—C23—H23A	109.6
C5—O1—Zn1	110.0 (2)	S3B—C23—H23A	114.9
C3—O2—C4	105.9 (3)	S3A—C23—H23B	109.4
S3B—O3—S3A	46.7 (11)	S3B—C23—H23B	75.1
S3B—O3—Zn1	171.4 (11)	H23A—C23—H23B	109.5
S3A—O3—Zn1	126.41 (19)	S3A—C23—H23C	109.4
C16—O4—Zn1	109.8 (2)	S3B—C23—H23C	130.7
C13—O5—C15	105.8 (4)	H23A—C23—H23C	109.5
C5—N1—N2	110.3 (2)	H23B—C23—H23C	109.5
C6—N2—N1	116.4 (3)	S3A—C23—H23D	118.7
C6—N2—Zn1	128.6 (2)	S3B—C23—H23D	107.4
N1—N2—Zn1	114.91 (19)	H23A—C23—H23D	25.7
C16—N3—N4	110.0 (3)	H23B—C23—H23D	83.9
C17—N4—N3	117.0 (3)	H23C—C23—H23D	122.0
C17—N4—Zn1	128.2 (2)	S3A—C23—H23E	127.1
N3—N4—Zn1	114.8 (2)	S3B—C23—H23E	111.1
C4—C1—C2	106.8 (3)	H23A—C23—H23E	123.4
C4—C1—H1B	126.6	H23B—C23—H23E	54.1
C2—C1—H1B	126.6	H23C—C23—H23E	55.4
C3—C2—C1	106.3 (4)	H23D—C23—H23E	109.5
C3—C2—H2A	126.8	S3A—C23—H23F	74.7
C1—C2—H2A	126.8	S3B—C23—H23F	110.0
C2—C3—O2	111.4 (3)	H23A—C23—H23F	84.0
C2—C3—H3B	124.3	H23B—C23—H23F	162.5
O2—C3—H3B	124.3	H23C—C23—H23F	54.2
C1—C4—O2	109.5 (3)	H23D—C23—H23F	109.5
C1—C4—C5	131.4 (3)	H23E—C23—H23F	109.5
O2—C4—C5	119.1 (3)	S3A—C24—S3B	35.3 (7)
O1—C5—N1	127.0 (3)	S3A—C24—H24A	109.5
O1—C5—C4	115.6 (3)	S3B—C24—H24A	116.6
N1—C5—C4	117.4 (3)	S3A—C24—H24C	109.5
N2—C6—C7	129.0 (3)	S3B—C24—H24C	74.8
N2—C6—H6A	115.5	H24A—C24—H24C	109.5
C7—C6—H6A	115.5	S3A—C24—H24D	109.5
C10—C7—C6	126.0 (3)	S3B—C24—H24D	129.1
C10—C7—S1	110.1 (3)	H24A—C24—H24D	109.5
C6—C7—S1	123.8 (3)	H24C—C24—H24D	109.5
C9—C8—S1	112.6 (3)	S3A—C24—H24B	117.7
C9—C8—H8A	123.7	S3B—C24—H24B	108.5
S1—C8—H8A	123.7	H24A—C24—H24B	25.0
C8—C9—C10	113.9 (4)	H24C—C24—H24B	84.6
C8—C9—H9A	123.0	H24D—C24—H24B	122.4
C10—C9—H9A	123.0	S3A—C24—H24E	74.0
C7—C10—C9	112.0 (4)	S3B—C24—H24E	109.0
C7—C10—C11	124.8 (4)	H24A—C24—H24E	84.6
C9—C10—C11	123.2 (4)	H24C—C24—H24E	162.4
C10—C11—H11A	109.5	H24D—C24—H24E	54.3
C10—C11—H11B	109.5	H24B—C24—H24E	109.5
H11A—C11—H11B	109.5	S3A—C24—H24F	128.4
C10—C11—H11C	109.5	S3B—C24—H24F	110.9
H11A—C11—H11C	109.5	H24A—C24—H24F	122.1
H11B—C11—H11C	109.5	H24C—C24—H24F	54.4
C15—C12—C14	107.3 (5)	H24D—C24—H24F	55.2
C15—C12—H12A	126.4	H24B—C24—H24F	109.5
C14—C12—H12A	126.4	H24E—C24—H24F	109.5
C14—C13—O5	111.3 (5)	O4—C16—N3	126.6 (3)
C14—C13—H13A	124.4	O4—C16—C15	119.2 (3)
O5—C13—H13A	124.4	N3—C16—C15	114.2 (3)
C13—C14—C12	106.4 (4)
O3—Zn1—O1—C5	−119.2 (2)	C1—C4—C5—O1	4.4 (6)
N4—Zn1—O1—C5	124.2 (2)	O2—C4—C5—O1	−177.1 (3)
N2—Zn1—O1—C5	−1.9 (2)	C1—C4—C5—N1	−174.7 (4)
O4—Zn1—O1—C5	80.7 (8)	O2—C4—C5—N1	3.8 (5)
C23—S3B—O3—S3A	64.2 (16)	N1—N2—C6—C7	−1.6 (6)
C24—S3B—O3—S3A	−61.3 (13)	Zn1—N2—C6—C7	−177.6 (3)
C23—S3B—O3—Zn1	104 (9)	N2—C6—C7—C10	−176.6 (4)
C24—S3B—O3—Zn1	−22 (11)	N2—C6—C7—S1	7.7 (6)
C24—S3A—O3—S3B	52.5 (17)	C8—S1—C7—C10	−0.3 (3)
C23—S3A—O3—S3B	−49.0 (17)	C8—S1—C7—C6	176.0 (3)
C24—S3A—O3—Zn1	−120.7 (3)	C7—S1—C8—C9	1.0 (4)
C23—S3A—O3—Zn1	137.8 (3)	S1—C8—C9—C10	−1.5 (5)
N4—Zn1—O3—S3B	105 (9)	C6—C7—C10—C9	−176.6 (4)
N2—Zn1—O3—S3B	−76 (9)	S1—C7—C10—C9	−0.5 (4)
O4—Zn1—O3—S3B	−178 (9)	C6—C7—C10—C11	5.1 (7)
O1—Zn1—O3—S3B	4 (9)	S1—C7—C10—C11	−178.7 (3)
N4—Zn1—O3—S3A	139.8 (3)	C8—C9—C10—C7	1.3 (5)
N2—Zn1—O3—S3A	−40.7 (3)	C8—C9—C10—C11	179.6 (4)
O4—Zn1—O3—S3A	−143.4 (3)	C15—O5—C13—C14	−1.5 (7)
O1—Zn1—O3—S3A	39.0 (3)	O5—C13—C14—C12	1.3 (8)
O3—Zn1—O4—C16	−109.3 (2)	C15—C12—C14—C13	−0.5 (7)
N4—Zn1—O4—C16	6.6 (2)	C14—C12—C15—O5	−0.3 (5)
N2—Zn1—O4—C16	132.1 (2)	C14—C12—C15—C16	179.9 (4)
O1—Zn1—O4—C16	50.9 (8)	C13—O5—C15—C12	1.1 (5)
C5—N1—N2—C6	−177.7 (3)	C13—O5—C15—C16	−179.1 (4)
C5—N1—N2—Zn1	−1.1 (4)	N3—N4—C17—C18	−2.4 (5)
O3—Zn1—N2—C6	−91.3 (3)	Zn1—N4—C17—C18	174.6 (3)
N4—Zn1—N2—C6	88.1 (3)	N4—C17—C18—C21	−174.2 (4)
O4—Zn1—N2—C6	4.7 (3)	N4—C17—C18—S2	1.9 (5)
O1—Zn1—N2—C6	177.7 (3)	C19—S2—C18—C21	−1.3 (3)
O3—Zn1—N2—N1	92.6 (2)	C19—S2—C18—C17	−177.8 (3)
N4—Zn1—N2—N1	−87.9 (2)	C18—S2—C19—C20	0.8 (4)
O4—Zn1—N2—N1	−171.4 (2)	S2—C19—C20—C21	−0.1 (6)
O1—Zn1—N2—N1	1.7 (2)	C17—C18—C21—C20	178.0 (3)
C16—N3—N4—C17	−176.2 (3)	S2—C18—C21—C20	1.4 (4)
C16—N3—N4—Zn1	6.4 (3)	C17—C18—C21—C22	−5.7 (6)
O3—Zn1—N4—C17	−100.0 (3)	S2—C18—C21—C22	177.7 (4)
N2—Zn1—N4—C17	80.5 (3)	C19—C20—C21—C18	−0.8 (6)
O4—Zn1—N4—C17	175.7 (3)	C19—C20—C21—C22	−177.1 (5)
O1—Zn1—N4—C17	0.5 (3)	O3—S3A—C23—S3B	34.2 (19)
O3—Zn1—N4—N3	77.0 (2)	C24—S3A—C23—S3B	−73.9 (19)
N2—Zn1—N4—N3	−102.5 (2)	O3—S3B—C23—S3A	−71.9 (18)
O4—Zn1—N4—N3	−7.3 (2)	C24—S3B—C23—S3A	65.5 (11)
O1—Zn1—N4—N3	177.6 (2)	O3—S3A—C24—S3B	−35.7 (12)
C4—C1—C2—C3	−0.1 (5)	C23—S3A—C24—S3B	71.2 (12)
C1—C2—C3—O2	0.1 (6)	O3—S3B—C24—S3A	71 (2)
C4—O2—C3—C2	0.0 (5)	C23—S3B—C24—S3A	−68.3 (10)
C2—C1—C4—O2	0.1 (5)	Zn1—O4—C16—N3	−5.8 (4)
C2—C1—C4—C5	178.7 (4)	Zn1—O4—C16—C15	174.8 (2)
C3—O2—C4—C1	0.0 (4)	N4—N3—C16—O4	−0.2 (5)
C3—O2—C4—C5	−178.8 (3)	N4—N3—C16—C15	179.2 (3)
Zn1—O1—C5—N1	2.1 (5)	C12—C15—C16—O4	176.4 (4)
Zn1—O1—C5—C4	−176.9 (2)	O5—C15—C16—O4	−3.4 (5)
N2—N1—C5—O1	−0.7 (5)	C12—C15—C16—N3	−3.1 (6)
N2—N1—C5—C4	178.3 (3)	O5—C15—C16—N3	177.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1^i	0.93	2.50	3.385 (5)	159
C20—H20A···O4^ii	0.93	2.46	3.308 (5)	152

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