The crystal structures and Hirshfeld surface analyses of four 3,5-diacetyl-2-methyl-2,3-di­hydro-1,3,4-thia­diazol-2-yl derivatives

The crystal structures of four 3,5-diacetyl-2-methyl-2,3-di­hydro-1,3,4-thia­diazol-2-yl derivatives, viz. 4-phenyl benzoate, 4-phenyl isobutyrate, 4-phenyl propionate and 4-phenyl cinnamate, are described and the inter­molecular contacts in the crystals are analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• Mean [sigma](C-C) = 0.004 Å
• Mean [sigma](C-C) = 0.003 Å
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.060
• wR factor = 0.226
• Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.7 Ratio
PLAT220_ALERT_2_C Non-Solvent  Resd 1  O   Ueq(max)/Ueq(min) Range        3.9 Ratio
PLAT222_ALERT_3_C Non-Solv.  Resd 1  H   Uiso(max)/Uiso(min) Range        4.3 Ratio
PLAT234_ALERT_4_C Large Hirshfeld Difference O3A      --C14A     .       0.17 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C15A     --C20A     .       0.19 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C16A     --C17A     .       0.17 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C18B     --C19B     .       0.17 Ang.
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of       C12B Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C8B Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including       S1A      0.106 Check
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C8B      -C13B            1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00585 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.838 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595         14 Report
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         16 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         36 Report
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.17 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          3 Report
PLAT174_ALERT_4_G The CIF-Embedded .res File Contains FLAT Records          1 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          4 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          2 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT230_ALERT_2_G Hirshfeld Test Diff for    O4A      --C14A     .       12.7 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C15A     --C16A     .        5.9 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        32% Note
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  2  )        32% Note
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O3D            104.2 Degree
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         18 Note
PLAT793_ALERT_4_G Model has Chirality at C6A         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C6B         (Centro SPGR)          S Verify
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        523 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        35% Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  15 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  23 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  14 ALERT type 2 Indicator that the structure model may be wrong or deficient
   9 ALERT type 3 Indicator that the structure quality may be low
  11 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: II


Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O1       --H1A      .     Please Check

Alert level C
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        4.2 Ratio
PLAT220_ALERT_2_C Non-Solvent  Resd 2  C   Ueq(max)/Ueq(min) Range        3.3 Ratio
PLAT222_ALERT_3_C Non-Solv.  Resd 1  H   Uiso(max)/Uiso(min) Range        4.8 Ratio
PLAT234_ALERT_4_C Large Hirshfeld Difference O4B      --C14B     .       0.17 Ang.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of       C14A Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of       C15A Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00417 Ang.
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H10B     ..H16G     .       2.12 Ang.
                                                    1+x,y,z  =      1_655 Check
PLAT415_ALERT_2_C Short Inter D-H..H-X       H1A      ..H7B2     .       2.05 Ang.
                                                  1-x,-y,-z  =      2_655 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         16 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         12 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ...       0.25 Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          6 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT300_ALERT_4_G Atom Site Occupancy of O1         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H1A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H1B        Constrained at        0.5 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        24% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  3          1.50 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1       ..C16'             2.33 Ang.
                                                      x,y,z  =      1_555 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         20 Note
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          3 Note
              H2 O
PLAT793_ALERT_4_G Model has Chirality at C6A         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C6B         (Centro SPGR)          R Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        242 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          5 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   9 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  26 ALERT level G = General information/check it is not something unexpected

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
  14 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: III



Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of       C10B Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of       C11B Check
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C8B      -C13B            1.37 Ang.

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         4% Note
PLAT432_ALERT_2_G Short Inter X...Y Contact  S1A      ..C14A             3.22 Ang.
                                                1-x,2-y,1-z  =      2_676 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         19 Note
PLAT793_ALERT_4_G Model has Chirality at C6A         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C6B         (Centro SPGR)          S Verify

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: IV


Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C4B Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of       C17B Check
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of        C24 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including       Cl1      0.186 Check
PLAT331_ALERT_2_C Small Aver Phenyl C-C Dist C17B      -C22B     .       1.37 Ang.
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C8B      -C13B            1.36 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00474 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3      ..S1B      .       3.38 Ang.
                                                  1+x,1+y,z  =      1_665 Check
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         74 Ang   3

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ...       0.50 Check
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.12 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         18 Note
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          3 Note
              C H Cl3
PLAT793_ALERT_4_G Model has Chirality at C6A         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C6B         (Centro SPGR)          R Verify
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...         30 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   9 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  11 ALERT level G = General information/check it is not something unexpected

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

For all structures, data collection: APEX2 (Bruker, 2008). Cell refinement: APEX2 (Bruker, 2008) for (I), (II); SAINT (Bruker, 2008) for (III), (IV). For all structures, data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS2018/3 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and PLATON (Spek, 2009).

4-(5-Acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl benzoate (I)

Crystal data

C20H19N3O4S	Z = 4
Mr = 397.44	F(000) = 832
Triclinic, P1	Dx = 1.310 Mg m^−3
a = 6.7559 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 16.9258 (2) Å	Cell parameters from 7061 reflections
c = 19.0611 (3) Å	θ = 1.2–25.0°
α = 110.447 (1)°	µ = 0.19 mm^−1
β = 96.854 (2)°	T = 293 K
γ = 93.370 (1)°	Block, colourless
V = 2015.84 (5) Å^3	0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	4821 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.029
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 25.0°, θmin = 1.2°
Tmin = 0.648, Tmax = 0.763	h = −8→8
27547 measured reflections	k = −17→20
7061 independent reflections	l = −22→22

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)] = 0.060	Hydrogen site location: mixed
wR(F^2) = 0.226	H atoms treated by a mixture of independent and constrained refinement
S = 0.83	w = 1/[σ^2(Fo^2) + (0.173P)^2 + 1.4455P] where P = (Fo^2 + 2Fc^2)/3
7061 reflections	(Δ/σ)max < 0.001
635 parameters	Δρmax = 0.38 e Å^−3
523 restraints	Δρmin = −0.56 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1A	0.2219 (6)	0.4068 (2)	0.0385 (2)	0.0656 (9)
H1A1	0.177958	0.462086	0.058777	0.098*
H1A2	0.184605	0.384459	−0.015565	0.098*
H1A3	0.364971	0.410730	0.050786	0.098*
C2A	0.1252 (5)	0.34900 (19)	0.07183 (18)	0.0543 (8)
C6A	0.0955 (5)	0.20448 (19)	0.08168 (18)	0.0520 (7)
C3A	0.3164 (4)	0.16342 (18)	−0.02111 (17)	0.0491 (7)
C4A	0.4572 (5)	0.0414 (2)	−0.10248 (19)	0.0609 (9)
C5A	0.6199 (7)	0.0180 (2)	−0.1495 (2)	0.0814 (11)
H5A1	0.746604	0.029517	−0.117187	0.122*
H5A2	0.621092	0.050733	−0.181743	0.122*
H5A3	0.597016	−0.041245	−0.180053	0.122*
C7A	−0.1299 (5)	0.1951 (2)	0.0779 (2)	0.0701 (10)
H7A1	−0.169166	0.243320	0.116042	0.105*
H7A2	−0.171080	0.144398	0.086486	0.105*
H7A3	−0.192434	0.191664	0.028849	0.105*
C8A	0.2146 (5)	0.22651 (19)	0.16091 (18)	0.0541 (8)
C9A	0.4050 (5)	0.2035 (2)	0.1704 (2)	0.0637 (9)
H9A	0.458678	0.170827	0.128259	0.076*
C10A	0.5187 (7)	0.2281 (3)	0.2417 (3)	0.0815 (12)
H10A	0.646125	0.211083	0.247511	0.098*
C11A	0.4406 (9)	0.2779 (3)	0.3036 (2)	0.0942 (15)
C12A	0.2516 (9)	0.3016 (3)	0.2952 (3)	0.1005 (15)
H12A	0.198292	0.334662	0.337239	0.121*
C13A	0.1417 (7)	0.2764 (3)	0.2247 (2)	0.0800 (11)
H13A	0.014074	0.293392	0.219469	0.096*
C5B	−0.3939 (6)	0.4189 (2)	0.1997 (3)	0.0781 (11)
H5B1	−0.316132	0.410587	0.241635	0.117*
H5B2	−0.362202	0.379959	0.153106	0.117*
H5B3	−0.534022	0.409008	0.201844	0.117*
C4B	−0.3463 (5)	0.5073 (2)	0.2036 (2)	0.0600 (8)
C3B	−0.1030 (5)	0.60085 (19)	0.17747 (17)	0.0491 (7)
C6B	0.0218 (5)	0.75618 (19)	0.21718 (18)	0.0544 (8)
C7B	−0.0680 (6)	0.8261 (2)	0.1948 (2)	0.0736 (10)
H7B1	0.037946	0.865664	0.193445	0.110*
H7B2	−0.150634	0.855154	0.231292	0.110*
H7B3	−0.147948	0.801636	0.145728	0.110*
C8B	0.1840 (5)	0.78728 (19)	0.28650 (17)	0.0544 (8)
C13B	0.2002 (7)	0.8682 (3)	0.3381 (2)	0.0900 (14)
H13B	0.116198	0.906477	0.329469	0.108*
C12B	0.3399 (9)	0.8936 (3)	0.4029 (3)	0.119 (2)
H12B	0.347492	0.948328	0.438345	0.143*
C11B	0.4662 (7)	0.8387 (3)	0.4147 (2)	0.0940 (14)
C10B	0.4553 (6)	0.7583 (3)	0.3638 (2)	0.0811 (11)
H10B	0.541883	0.720683	0.372222	0.097*
C9B	0.3147 (6)	0.7332 (2)	0.2996 (2)	0.0699 (10)
H9B	0.308075	0.678469	0.264329	0.084*
C2B	0.2436 (5)	0.7107 (2)	0.11765 (19)	0.0609 (8)
C1B	0.3273 (6)	0.6394 (2)	0.0626 (2)	0.0734 (10)
H1B1	0.415555	0.661491	0.036299	0.110*
H1B2	0.219721	0.601912	0.026726	0.110*
H1B3	0.400488	0.608835	0.089090	0.110*
N1A	0.1674 (4)	0.26824 (15)	0.04924 (14)	0.0506 (6)
N2A	0.3109 (4)	0.24387 (15)	0.00068 (14)	0.0499 (6)
N3A	0.4450 (4)	0.12653 (16)	−0.07072 (15)	0.0528 (6)
H3A	0.515 (5)	0.152 (2)	−0.0914 (18)	0.051 (9)*
N1B	0.0966 (4)	0.69192 (15)	0.15279 (14)	0.0532 (6)
N2B	0.0369 (4)	0.60619 (15)	0.13948 (14)	0.0529 (6)
N3B	−0.1812 (4)	0.52161 (17)	0.17374 (16)	0.0549 (7)
H3B	−0.117 (6)	0.482 (3)	0.151 (2)	0.080 (13)*
O1A	0.0081 (4)	0.37406 (15)	0.11807 (15)	0.0726 (7)
O2A	0.3441 (5)	−0.00950 (15)	−0.09099 (17)	0.0862 (8)
O1B	0.3065 (4)	0.78560 (15)	0.13218 (16)	0.0791 (8)
O2B	−0.4457 (4)	0.56429 (18)	0.23256 (19)	0.0913 (9)
S1A	0.15994 (13)	0.10508 (5)	0.01356 (5)	0.0586 (3)
S1B	−0.18822 (13)	0.69320 (5)	0.23393 (6)	0.0656 (3)
C14A	0.697 (2)	0.3397 (10)	0.4045 (6)	0.121 (3)	0.553 (5)
C15A	0.7452 (13)	0.3657 (5)	0.4903 (3)	0.113 (3)	0.553 (5)
C16A	0.9402 (12)	0.3664 (6)	0.5236 (5)	0.175 (4)	0.553 (5)
H16A	1.032983	0.338544	0.494131	0.210*	0.553 (5)
C17A	0.9967 (13)	0.4088 (7)	0.6011 (5)	0.181 (5)	0.553 (5)
H17A	1.127142	0.409308	0.623366	0.217*	0.553 (5)
C18A	0.8581 (17)	0.4505 (6)	0.6452 (3)	0.172 (5)	0.553 (5)
H18A	0.895807	0.478825	0.696988	0.207*	0.553 (5)
C19A	0.6630 (15)	0.4497 (6)	0.6119 (4)	0.155 (4)	0.553 (5)
H19A	0.570311	0.477579	0.641375	0.185*	0.553 (5)
C20A	0.6066 (11)	0.4073 (5)	0.5344 (4)	0.138 (4)	0.553 (5)
H20A	0.476148	0.406815	0.512140	0.165*	0.553 (5)
O3A	0.5068 (13)	0.3112 (7)	0.3822 (5)	0.102 (3)	0.553 (5)
O4A	0.754 (3)	0.3795 (13)	0.3656 (12)	0.280 (10)	0.553 (5)
C14C	0.799 (2)	0.3142 (11)	0.3741 (8)	0.121 (4)	0.447 (5)
C15C	0.8754 (14)	0.3580 (5)	0.4579 (4)	0.120 (3)	0.447 (5)
C16C	0.8530 (11)	0.3003 (5)	0.4941 (4)	0.091 (3)	0.447 (5)
H16C	0.754803	0.254222	0.473476	0.110*	0.447 (5)
C17C	0.9775 (14)	0.3113 (6)	0.5611 (4)	0.117 (4)	0.447 (5)
H17C	0.962484	0.272708	0.585356	0.141*	0.447 (5)
C18C	1.1243 (15)	0.3801 (7)	0.5920 (4)	0.157 (5)	0.447 (5)
H18C	1.207516	0.387540	0.636820	0.189*	0.447 (5)
C19C	1.1466 (16)	0.4379 (6)	0.5558 (6)	0.176 (5)	0.447 (5)
H19C	1.244869	0.483887	0.576403	0.212*	0.447 (5)
C20C	1.0222 (17)	0.4268 (6)	0.4887 (5)	0.162 (5)	0.447 (5)
H20C	1.037190	0.465403	0.464522	0.194*	0.447 (5)
O3C	0.5988 (14)	0.2887 (7)	0.3676 (6)	0.088 (3)	0.447 (5)
O4C	0.825 (2)	0.3587 (10)	0.3401 (9)	0.173 (6)	0.447 (5)
C14B	0.7656 (13)	0.8772 (6)	0.4908 (5)	0.083 (2)	0.661 (6)
C15B	0.8793 (11)	0.8962 (5)	0.5669 (3)	0.073 (2)	0.661 (6)
C16B	0.7909 (7)	0.8815 (4)	0.6240 (5)	0.085 (2)	0.661 (6)
H16B	0.656588	0.860085	0.614983	0.103*	0.661 (6)
C17B	0.9034 (15)	0.8987 (4)	0.6947 (4)	0.095 (2)	0.661 (6)
H17B	0.844281	0.888860	0.732942	0.114*	0.661 (6)
C18B	1.1042 (14)	0.9306 (5)	0.7082 (3)	0.092 (3)	0.661 (6)
H18B	1.179435	0.942175	0.755513	0.110*	0.661 (6)
C19B	1.1925 (6)	0.9453 (6)	0.6511 (5)	0.120 (3)	0.661 (6)
H19B	1.326900	0.966716	0.660124	0.144*	0.661 (6)
C20B	1.0801 (13)	0.9281 (6)	0.5804 (4)	0.110 (3)	0.661 (6)
H20B	1.139211	0.937942	0.542164	0.132*	0.661 (6)
O3B	0.5721 (8)	0.8573 (4)	0.4871 (3)	0.0906 (17)	0.661 (6)
O4B	0.8318 (9)	0.8830 (5)	0.4386 (3)	0.149 (3)	0.661 (6)
C14D	0.6548 (19)	0.8629 (9)	0.5293 (7)	0.083 (3)	0.339 (6)
C15D	0.8356 (19)	0.8907 (10)	0.5852 (9)	0.072 (3)	0.339 (6)
C16D	0.8392 (18)	0.8858 (10)	0.6566 (11)	0.093 (4)	0.339 (6)
H16D	0.725040	0.863845	0.669272	0.112*	0.339 (6)
C17D	1.013 (3)	0.9138 (10)	0.7091 (6)	0.093 (4)	0.339 (6)
H17D	1.015712	0.910545	0.756882	0.112*	0.339 (6)
C18D	1.1839 (19)	0.9466 (10)	0.6901 (8)	0.104 (5)	0.339 (6)
H18D	1.300469	0.965352	0.725262	0.124*	0.339 (6)
C19D	1.1804 (18)	0.9515 (11)	0.6187 (11)	0.113 (5)	0.339 (6)
H19D	1.294556	0.973460	0.606031	0.136*	0.339 (6)
C20D	1.006 (3)	0.9235 (12)	0.5662 (6)	0.096 (4)	0.339 (6)
H20D	1.003885	0.926762	0.518420	0.115*	0.339 (6)
O3D	0.6689 (19)	0.8790 (7)	0.4661 (6)	0.079 (3)	0.339 (6)
O4D	0.5080 (18)	0.8298 (9)	0.5407 (6)	0.139 (5)	0.339 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.082 (2)	0.0410 (17)	0.081 (2)	0.0079 (16)	0.0187 (19)	0.0279 (16)
C2A	0.0599 (19)	0.0410 (17)	0.0619 (19)	0.0019 (14)	0.0021 (16)	0.0213 (14)
C6A	0.0518 (17)	0.0407 (16)	0.0654 (19)	−0.0048 (13)	0.0018 (14)	0.0252 (14)
C3A	0.0515 (17)	0.0377 (15)	0.0538 (17)	−0.0053 (13)	−0.0075 (13)	0.0176 (13)
C4A	0.075 (2)	0.0353 (16)	0.067 (2)	0.0000 (15)	−0.0002 (17)	0.0158 (14)
C5A	0.098 (3)	0.045 (2)	0.099 (3)	0.0096 (19)	0.028 (2)	0.0174 (19)
C7A	0.0519 (19)	0.062 (2)	0.097 (3)	−0.0067 (16)	0.0034 (18)	0.034 (2)
C8A	0.0619 (19)	0.0423 (16)	0.0616 (19)	−0.0037 (14)	0.0047 (15)	0.0261 (14)
C9A	0.065 (2)	0.057 (2)	0.072 (2)	−0.0024 (16)	−0.0038 (17)	0.0322 (17)
C10A	0.080 (3)	0.074 (3)	0.092 (3)	−0.016 (2)	−0.024 (2)	0.047 (2)
C11A	0.125 (4)	0.093 (3)	0.062 (3)	−0.035 (3)	−0.020 (3)	0.042 (2)
C12A	0.134 (5)	0.099 (4)	0.061 (3)	−0.004 (3)	0.009 (3)	0.023 (2)
C13A	0.084 (3)	0.082 (3)	0.073 (3)	0.008 (2)	0.013 (2)	0.027 (2)
C5B	0.073 (2)	0.064 (2)	0.107 (3)	−0.0018 (18)	0.020 (2)	0.043 (2)
C4B	0.0521 (18)	0.056 (2)	0.073 (2)	0.0013 (15)	0.0055 (16)	0.0262 (16)
C3B	0.0529 (17)	0.0436 (16)	0.0526 (16)	0.0054 (13)	0.0018 (14)	0.0212 (13)
C6B	0.0614 (19)	0.0404 (16)	0.0644 (19)	0.0082 (14)	0.0101 (15)	0.0217 (14)
C7B	0.090 (3)	0.052 (2)	0.083 (2)	0.0200 (18)	0.004 (2)	0.0297 (18)
C8B	0.0645 (19)	0.0435 (17)	0.0562 (17)	0.0099 (14)	0.0134 (15)	0.0171 (14)
C13B	0.109 (3)	0.061 (2)	0.081 (3)	0.032 (2)	−0.011 (2)	0.006 (2)
C12B	0.151 (5)	0.076 (3)	0.089 (3)	0.040 (3)	−0.028 (3)	−0.010 (2)
C11B	0.104 (3)	0.091 (3)	0.066 (2)	0.024 (3)	−0.011 (2)	0.007 (2)
C10B	0.082 (3)	0.079 (3)	0.077 (2)	0.027 (2)	−0.002 (2)	0.024 (2)
C9B	0.077 (2)	0.050 (2)	0.074 (2)	0.0149 (17)	0.0007 (18)	0.0138 (17)
C2B	0.077 (2)	0.0447 (18)	0.066 (2)	0.0031 (16)	0.0133 (17)	0.0249 (15)
C1B	0.085 (3)	0.054 (2)	0.084 (2)	0.0020 (18)	0.032 (2)	0.0234 (18)
N1A	0.0557 (15)	0.0389 (13)	0.0590 (15)	−0.0014 (11)	0.0023 (12)	0.0229 (11)
N2A	0.0564 (15)	0.0360 (13)	0.0583 (14)	0.0016 (11)	0.0047 (12)	0.0199 (11)
N3A	0.0611 (16)	0.0358 (13)	0.0615 (16)	0.0002 (12)	0.0074 (13)	0.0189 (12)
N1B	0.0659 (16)	0.0385 (13)	0.0576 (15)	0.0036 (11)	0.0121 (12)	0.0196 (11)
N2B	0.0680 (17)	0.0386 (13)	0.0544 (14)	0.0030 (12)	0.0096 (13)	0.0200 (11)
N3B	0.0613 (17)	0.0411 (14)	0.0644 (16)	0.0038 (12)	0.0119 (13)	0.0210 (12)
O1A	0.0828 (17)	0.0490 (13)	0.0951 (18)	0.0128 (12)	0.0308 (15)	0.0305 (12)
O2A	0.106 (2)	0.0383 (13)	0.108 (2)	−0.0094 (13)	0.0260 (17)	0.0185 (13)
O1B	0.1010 (19)	0.0472 (14)	0.0968 (19)	0.0003 (13)	0.0338 (15)	0.0304 (13)
O2B	0.0716 (17)	0.0696 (18)	0.141 (3)	0.0123 (14)	0.0387 (17)	0.0395 (18)
S1A	0.0671 (5)	0.0373 (4)	0.0682 (5)	−0.0104 (3)	0.0025 (4)	0.0201 (4)
S1B	0.0620 (5)	0.0485 (5)	0.0884 (7)	0.0101 (4)	0.0214 (5)	0.0231 (4)
C14A	0.124 (7)	0.141 (7)	0.074 (6)	−0.007 (6)	−0.023 (5)	0.021 (5)
C15A	0.120 (7)	0.113 (6)	0.078 (5)	−0.017 (5)	−0.029 (5)	0.020 (5)
C16A	0.181 (7)	0.174 (7)	0.131 (6)	−0.015 (7)	−0.035 (6)	0.029 (6)
C17A	0.193 (10)	0.194 (9)	0.106 (7)	−0.027 (8)	−0.068 (7)	0.029 (7)
C18A	0.220 (12)	0.186 (11)	0.090 (7)	−0.049 (10)	−0.044 (8)	0.058 (7)
C19A	0.208 (11)	0.159 (9)	0.089 (6)	−0.044 (8)	−0.003 (7)	0.053 (6)
C20A	0.188 (10)	0.130 (8)	0.089 (6)	−0.027 (7)	0.001 (6)	0.046 (6)
O3A	0.097 (6)	0.141 (7)	0.063 (4)	−0.025 (5)	−0.008 (4)	0.041 (4)
O4A	0.241 (16)	0.301 (16)	0.181 (14)	−0.081 (14)	−0.011 (12)	−0.026 (13)
C14C	0.113 (8)	0.165 (9)	0.072 (7)	−0.030 (7)	−0.020 (6)	0.043 (7)
C15C	0.143 (8)	0.130 (7)	0.075 (6)	−0.036 (6)	−0.035 (5)	0.046 (5)
C16C	0.100 (6)	0.097 (6)	0.072 (5)	0.004 (5)	−0.015 (5)	0.033 (5)
C17C	0.145 (8)	0.136 (8)	0.078 (6)	0.008 (7)	−0.018 (6)	0.059 (6)
C18C	0.195 (11)	0.151 (9)	0.113 (7)	−0.007 (8)	−0.052 (8)	0.059 (7)
C19C	0.221 (10)	0.163 (9)	0.125 (8)	−0.058 (8)	−0.062 (8)	0.067 (7)
C20C	0.199 (10)	0.142 (9)	0.126 (8)	−0.065 (8)	−0.077 (8)	0.071 (7)
O3C	0.087 (6)	0.116 (6)	0.063 (5)	−0.021 (5)	−0.014 (4)	0.047 (4)
O4C	0.114 (8)	0.234 (14)	0.110 (9)	−0.007 (8)	−0.009 (7)	−0.001 (9)
C14B	0.079 (5)	0.095 (4)	0.079 (5)	0.005 (4)	0.006 (4)	0.038 (4)
C15B	0.059 (4)	0.073 (4)	0.083 (4)	−0.001 (3)	0.001 (3)	0.027 (3)
C16B	0.088 (4)	0.085 (4)	0.077 (5)	0.000 (4)	−0.010 (4)	0.029 (4)
C17B	0.089 (6)	0.099 (5)	0.086 (5)	−0.009 (4)	−0.013 (4)	0.030 (4)
C18B	0.085 (6)	0.105 (5)	0.078 (4)	0.004 (5)	−0.004 (4)	0.031 (4)
C19B	0.085 (5)	0.163 (6)	0.092 (7)	−0.002 (5)	−0.014 (5)	0.033 (6)
C20B	0.082 (6)	0.150 (6)	0.087 (5)	−0.008 (5)	−0.009 (4)	0.039 (5)
O3B	0.076 (3)	0.119 (4)	0.062 (3)	0.006 (3)	0.000 (3)	0.018 (3)
O4B	0.100 (4)	0.248 (8)	0.107 (4)	−0.043 (4)	−0.012 (3)	0.092 (5)
C14D	0.078 (6)	0.089 (6)	0.078 (6)	0.006 (6)	0.014 (6)	0.027 (5)
C15D	0.078 (6)	0.074 (6)	0.069 (6)	0.007 (6)	0.002 (6)	0.034 (5)
C16D	0.083 (7)	0.100 (7)	0.089 (8)	−0.006 (6)	−0.026 (7)	0.039 (7)
C17D	0.085 (9)	0.103 (7)	0.087 (6)	−0.009 (8)	−0.011 (7)	0.041 (6)
C18D	0.082 (8)	0.134 (9)	0.082 (9)	0.008 (8)	−0.012 (8)	0.031 (8)
C19D	0.088 (8)	0.151 (8)	0.084 (9)	0.002 (7)	−0.019 (7)	0.034 (8)
C20D	0.069 (8)	0.123 (7)	0.085 (6)	0.007 (7)	−0.009 (6)	0.030 (6)
O3D	0.069 (7)	0.095 (6)	0.071 (6)	−0.004 (5)	0.003 (5)	0.033 (5)
O4D	0.114 (8)	0.198 (12)	0.100 (8)	−0.038 (8)	0.002 (6)	0.062 (8)

Geometric parameters (Å, º)

C1A—C2A	1.499 (5)	C2B—C1B	1.488 (5)
C1A—H1A1	0.9600	C1B—H1B1	0.9600
C1A—H1A2	0.9600	C1B—H1B2	0.9600
C1A—H1A3	0.9600	C1B—H1B3	0.9600
C2A—O1A	1.236 (4)	N1A—N2A	1.400 (4)
C2A—N1A	1.341 (4)	N3A—H3A	0.84 (3)
C6A—N1A	1.503 (4)	N1B—N2B	1.408 (3)
C6A—C7A	1.512 (5)	N3B—H3B	0.85 (4)
C6A—C8A	1.533 (4)	C14A—O4A	1.239 (16)
C6A—S1A	1.844 (3)	C14A—O3A	1.312 (13)
C3A—N2A	1.282 (4)	C14A—C15A	1.526 (11)
C3A—N3A	1.373 (4)	C15A—C16A	1.3900
C3A—S1A	1.740 (3)	C15A—C20A	1.3900
C4A—O2A	1.212 (4)	C16A—C17A	1.3900
C4A—N3A	1.366 (4)	C16A—H16A	0.9300
C4A—C5A	1.485 (5)	C17A—C18A	1.3900
C5A—H5A1	0.9600	C17A—H17A	0.9300
C5A—H5A2	0.9600	C18A—C19A	1.3900
C5A—H5A3	0.9600	C18A—H18A	0.9300
C7A—H7A1	0.9600	C19A—C20A	1.3900
C7A—H7A2	0.9600	C19A—H19A	0.9300
C7A—H7A3	0.9600	C20A—H20A	0.9300
C8A—C9A	1.376 (5)	C14C—O4C	1.171 (15)
C8A—C13A	1.382 (5)	C14C—O3C	1.370 (15)
C9A—C10A	1.389 (5)	C14C—C15C	1.517 (13)
C9A—H9A	0.9300	C15C—C16C	1.3900
C10A—C11A	1.374 (7)	C15C—C20C	1.3900
C10A—H10A	0.9300	C16C—C17C	1.3900
C11A—C12A	1.369 (7)	C16C—H16C	0.9300
C11A—O3A	1.407 (10)	C17C—C18C	1.3900
C11A—O3C	1.473 (11)	C17C—H17C	0.9300
C12A—C13A	1.364 (6)	C18C—C19C	1.3900
C12A—H12A	0.9300	C18C—H18C	0.9300
C13A—H13A	0.9300	C19C—C20C	1.3900
C5B—C4B	1.487 (5)	C19C—H19C	0.9300
C5B—H5B1	0.9600	C20C—H20C	0.9300
C5B—H5B2	0.9600	C14B—O4B	1.170 (9)
C5B—H5B3	0.9600	C14B—O3B	1.318 (9)
C4B—O2B	1.216 (4)	C14B—C15B	1.476 (9)
C4B—N3B	1.357 (4)	C15B—C16B	1.3900
C3B—N2B	1.275 (4)	C15B—C20B	1.3900
C3B—N3B	1.387 (4)	C16B—C17B	1.3900
C3B—S1B	1.735 (3)	C16B—H16B	0.9300
C6B—N1B	1.492 (4)	C17B—C18B	1.3900
C6B—C8B	1.525 (5)	C17B—H17B	0.9300
C6B—C7B	1.525 (4)	C18B—C19B	1.3900
C6B—S1B	1.849 (3)	C18B—H18B	0.9300
C7B—H7B1	0.9600	C19B—C20B	1.3900
C7B—H7B2	0.9600	C19B—H19B	0.9300
C7B—H7B3	0.9600	C20B—H20B	0.9300
C8B—C13B	1.368 (5)	C14D—O4D	1.190 (13)
C8B—C9B	1.372 (5)	C14D—O3D	1.336 (13)
C13B—C12B	1.380 (6)	C14D—C15D	1.456 (13)
C13B—H13B	0.9300	C15D—C16D	1.3900
C12B—C11B	1.355 (6)	C15D—C20D	1.3900
C12B—H12B	0.9300	C16D—C17D	1.3900
C11B—C10B	1.360 (6)	C16D—H16D	0.9300
C11B—O3B	1.396 (7)	C17D—C18D	1.3900
C11B—O3D	1.551 (13)	C17D—H17D	0.9300
C10B—C9B	1.376 (5)	C18D—C19D	1.3900
C10B—H10B	0.9300	C18D—H18D	0.9300
C9B—H9B	0.9300	C19D—C20D	1.3900
C2B—O1B	1.236 (4)	C19D—H19D	0.9300
C2B—N1B	1.344 (4)	C20D—H20D	0.9300
C2A—C1A—H1A1	109.5	H1B2—C1B—H1B3	109.5
C2A—C1A—H1A2	109.5	C2A—N1A—N2A	118.7 (2)
H1A1—C1A—H1A2	109.5	C2A—N1A—C6A	124.3 (3)
C2A—C1A—H1A3	109.5	N2A—N1A—C6A	116.3 (2)
H1A1—C1A—H1A3	109.5	C3A—N2A—N1A	110.0 (2)
H1A2—C1A—H1A3	109.5	C4A—N3A—C3A	125.3 (3)
O1A—C2A—N1A	120.5 (3)	C4A—N3A—H3A	109 (2)
O1A—C2A—C1A	121.6 (3)	C3A—N3A—H3A	125 (2)
N1A—C2A—C1A	117.9 (3)	C2B—N1B—N2B	118.8 (3)
N1A—C6A—C7A	112.8 (3)	C2B—N1B—C6B	123.3 (3)
N1A—C6A—C8A	108.2 (2)	N2B—N1B—C6B	116.6 (2)
C7A—C6A—C8A	115.0 (3)	C3B—N2B—N1B	109.9 (2)
N1A—C6A—S1A	101.4 (2)	C4B—N3B—C3B	124.4 (3)
C7A—C6A—S1A	106.6 (2)	C4B—N3B—H3B	122 (3)
C8A—C6A—S1A	112.1 (2)	C3B—N3B—H3B	114 (3)
N2A—C3A—N3A	119.0 (3)	C3A—S1A—C6A	89.90 (14)
N2A—C3A—S1A	118.5 (2)	C3B—S1B—C6B	89.66 (14)
N3A—C3A—S1A	122.5 (2)	O4A—C14A—O3A	110.2 (13)
O2A—C4A—N3A	121.1 (3)	O4A—C14A—C15A	126.8 (15)
O2A—C4A—C5A	124.0 (3)	O3A—C14A—C15A	109.7 (10)
N3A—C4A—C5A	114.8 (3)	C16A—C15A—C20A	120.0
C4A—C5A—H5A1	109.5	C16A—C15A—C14A	119.7 (7)
C4A—C5A—H5A2	109.5	C20A—C15A—C14A	118.4 (8)
H5A1—C5A—H5A2	109.5	C15A—C16A—C17A	120.0
C4A—C5A—H5A3	109.5	C15A—C16A—H16A	120.0
H5A1—C5A—H5A3	109.5	C17A—C16A—H16A	120.0
H5A2—C5A—H5A3	109.5	C18A—C17A—C16A	120.0
C6A—C7A—H7A1	109.5	C18A—C17A—H17A	120.0
C6A—C7A—H7A2	109.5	C16A—C17A—H17A	120.0
H7A1—C7A—H7A2	109.5	C17A—C18A—C19A	120.0
C6A—C7A—H7A3	109.5	C17A—C18A—H18A	120.0
H7A1—C7A—H7A3	109.5	C19A—C18A—H18A	120.0
H7A2—C7A—H7A3	109.5	C20A—C19A—C18A	120.0
C9A—C8A—C13A	117.6 (3)	C20A—C19A—H19A	120.0
C9A—C8A—C6A	121.0 (3)	C18A—C19A—H19A	120.0
C13A—C8A—C6A	121.1 (3)	C19A—C20A—C15A	120.0
C8A—C9A—C10A	121.2 (4)	C19A—C20A—H20A	120.0
C8A—C9A—H9A	119.4	C15A—C20A—H20A	120.0
C10A—C9A—H9A	119.4	C14A—O3A—C11A	117.1 (8)
C11A—C10A—C9A	119.2 (4)	O4C—C14C—O3C	111.6 (14)
C11A—C10A—H10A	120.4	O4C—C14C—C15C	111.8 (14)
C9A—C10A—H10A	120.4	O3C—C14C—C15C	107.0 (12)
C12A—C11A—C10A	120.3 (4)	C16C—C15C—C20C	120.0
C12A—C11A—O3A	104.9 (6)	C16C—C15C—C14C	109.1 (8)
C10A—C11A—O3A	134.7 (6)	C20C—C15C—C14C	125.1 (7)
C12A—C11A—O3C	136.1 (6)	C15C—C16C—C17C	120.0
C10A—C11A—O3C	103.5 (6)	C15C—C16C—H16C	120.0
C13A—C12A—C11A	119.7 (5)	C17C—C16C—H16C	120.0
C13A—C12A—H12A	120.2	C16C—C17C—C18C	120.0
C11A—C12A—H12A	120.2	C16C—C17C—H17C	120.0
C12A—C13A—C8A	121.9 (4)	C18C—C17C—H17C	120.0
C12A—C13A—H13A	119.0	C17C—C18C—C19C	120.0
C8A—C13A—H13A	119.0	C17C—C18C—H18C	120.0
C4B—C5B—H5B1	109.5	C19C—C18C—H18C	120.0
C4B—C5B—H5B2	109.5	C20C—C19C—C18C	120.0
H5B1—C5B—H5B2	109.5	C20C—C19C—H19C	120.0
C4B—C5B—H5B3	109.5	C18C—C19C—H19C	120.0
H5B1—C5B—H5B3	109.5	C19C—C20C—C15C	120.0
H5B2—C5B—H5B3	109.5	C19C—C20C—H20C	120.0
O2B—C4B—N3B	121.3 (3)	C15C—C20C—H20C	120.0
O2B—C4B—C5B	122.8 (3)	C14C—O3C—C11A	127.5 (9)
N3B—C4B—C5B	115.8 (3)	O4B—C14B—O3B	121.2 (8)
N2B—C3B—N3B	119.3 (3)	O4B—C14B—C15B	125.6 (8)
N2B—C3B—S1B	119.1 (2)	O3B—C14B—C15B	113.1 (7)
N3B—C3B—S1B	121.5 (2)	C16B—C15B—C20B	120.0
N1B—C6B—C8B	110.0 (2)	C16B—C15B—C14B	121.5 (8)
N1B—C6B—C7B	112.3 (3)	C20B—C15B—C14B	118.5 (8)
C8B—C6B—C7B	114.9 (3)	C17B—C16B—C15B	120.0
N1B—C6B—S1B	102.0 (2)	C17B—C16B—H16B	120.0
C8B—C6B—S1B	110.0 (2)	C15B—C16B—H16B	120.0
C7B—C6B—S1B	106.8 (2)	C16B—C17B—C18B	120.0
C6B—C7B—H7B1	109.5	C16B—C17B—H17B	120.0
C6B—C7B—H7B2	109.5	C18B—C17B—H17B	120.0
H7B1—C7B—H7B2	109.5	C19B—C18B—C17B	120.0
C6B—C7B—H7B3	109.5	C19B—C18B—H18B	120.0
H7B1—C7B—H7B3	109.5	C17B—C18B—H18B	120.0
H7B2—C7B—H7B3	109.5	C18B—C19B—C20B	120.0
C13B—C8B—C9B	118.3 (3)	C18B—C19B—H19B	120.0
C13B—C8B—C6B	121.5 (3)	C20B—C19B—H19B	120.0
C9B—C8B—C6B	120.2 (3)	C19B—C20B—C15B	120.0
C8B—C13B—C12B	120.7 (4)	C19B—C20B—H20B	120.0
C8B—C13B—H13B	119.6	C15B—C20B—H20B	120.0
C12B—C13B—H13B	119.6	C14B—O3B—C11B	112.7 (7)
C11B—C12B—C13B	119.8 (4)	O4D—C14D—O3D	124.1 (14)
C11B—C12B—H12B	120.1	O4D—C14D—C15D	121.6 (14)
C13B—C12B—H12B	120.1	O3D—C14D—C15D	114.3 (13)
C12B—C11B—C10B	120.7 (4)	C16D—C15D—C20D	120.0
C12B—C11B—O3B	118.9 (4)	C16D—C15D—C14D	121.3 (16)
C10B—C11B—O3B	118.4 (5)	C20D—C15D—C14D	118.7 (16)
C12B—C11B—O3D	116.0 (6)	C17D—C16D—C15D	120.0
C10B—C11B—O3D	118.4 (6)	C17D—C16D—H16D	120.0
C11B—C10B—C9B	119.1 (4)	C15D—C16D—H16D	120.0
C11B—C10B—H10B	120.4	C16D—C17D—C18D	120.0
C9B—C10B—H10B	120.4	C16D—C17D—H17D	120.0
C8B—C9B—C10B	121.4 (3)	C18D—C17D—H17D	120.0
C8B—C9B—H9B	119.3	C19D—C18D—C17D	120.0
C10B—C9B—H9B	119.3	C19D—C18D—H18D	120.0
O1B—C2B—N1B	119.7 (3)	C17D—C18D—H18D	120.0
O1B—C2B—C1B	122.1 (3)	C18D—C19D—C20D	120.0
N1B—C2B—C1B	118.2 (3)	C18D—C19D—H19D	120.0
C2B—C1B—H1B1	109.5	C20D—C19D—H19D	120.0
C2B—C1B—H1B2	109.5	C19D—C20D—C15D	120.0
H1B1—C1B—H1B2	109.5	C19D—C20D—H20D	120.0
C2B—C1B—H1B3	109.5	C15D—C20D—H20D	120.0
H1B1—C1B—H1B3	109.5	C14D—O3D—C11B	104.3 (10)
N1A—C6A—C8A—C9A	−80.2 (3)	N3A—C3A—S1A—C6A	170.4 (3)
C7A—C6A—C8A—C9A	152.7 (3)	N1A—C6A—S1A—C3A	15.58 (19)
S1A—C6A—C8A—C9A	30.8 (3)	C7A—C6A—S1A—C3A	133.8 (2)
N1A—C6A—C8A—C13A	94.1 (4)	C8A—C6A—S1A—C3A	−99.6 (2)
C7A—C6A—C8A—C13A	−33.0 (4)	N2B—C3B—S1B—C6B	−9.2 (3)
S1A—C6A—C8A—C13A	−155.0 (3)	N3B—C3B—S1B—C6B	169.8 (3)
C13A—C8A—C9A—C10A	1.2 (5)	N1B—C6B—S1B—C3B	13.5 (2)
C6A—C8A—C9A—C10A	175.7 (3)	C8B—C6B—S1B—C3B	−103.2 (2)
C8A—C9A—C10A—C11A	−1.4 (6)	C7B—C6B—S1B—C3B	131.5 (2)
C9A—C10A—C11A—C12A	1.2 (6)	O4A—C14A—C15A—C16A	−68 (2)
C9A—C10A—C11A—O3A	177.2 (7)	O3A—C14A—C15A—C16A	155.3 (9)
C9A—C10A—C11A—O3C	178.7 (5)	O4A—C14A—C15A—C20A	96 (2)
C10A—C11A—C12A—C13A	−0.8 (7)	O3A—C14A—C15A—C20A	−40.2 (14)
O3A—C11A—C12A—C13A	−177.9 (6)	C20A—C15A—C16A—C17A	0.0
O3C—C11A—C12A—C13A	−177.4 (7)	C14A—C15A—C16A—C17A	164.3 (10)
C11A—C12A—C13A—C8A	0.7 (7)	C15A—C16A—C17A—C18A	0.0
C9A—C8A—C13A—C12A	−0.9 (6)	C16A—C17A—C18A—C19A	0.0
C6A—C8A—C13A—C12A	−175.4 (4)	C17A—C18A—C19A—C20A	0.0
N1B—C6B—C8B—C13B	148.5 (4)	C18A—C19A—C20A—C15A	0.0
C7B—C6B—C8B—C13B	20.6 (5)	C16A—C15A—C20A—C19A	0.0
S1B—C6B—C8B—C13B	−100.0 (4)	C14A—C15A—C20A—C19A	−164.5 (9)
N1B—C6B—C8B—C9B	−33.4 (4)	O4A—C14A—O3A—C11A	41 (2)
C7B—C6B—C8B—C9B	−161.2 (3)	C15A—C14A—O3A—C11A	−174.9 (9)
S1B—C6B—C8B—C9B	78.1 (4)	C12A—C11A—O3A—C14A	−143.6 (10)
C9B—C8B—C13B—C12B	−2.2 (7)	C10A—C11A—O3A—C14A	40.0 (14)
C6B—C8B—C13B—C12B	175.9 (5)	O4C—C14C—C15C—C16C	−175.6 (14)
C8B—C13B—C12B—C11B	1.7 (9)	O3C—C14C—C15C—C16C	61.9 (14)
C13B—C12B—C11B—C10B	−0.7 (10)	O4C—C14C—C15C—C20C	−23 (2)
C13B—C12B—C11B—O3B	−164.8 (6)	O3C—C14C—C15C—C20C	−145.4 (9)
C13B—C12B—C11B—O3D	154.3 (7)	C20C—C15C—C16C—C17C	0.0
C12B—C11B—C10B—C9B	0.3 (8)	C14C—C15C—C16C—C17C	154.3 (10)
O3B—C11B—C10B—C9B	164.5 (5)	C15C—C16C—C17C—C18C	0.0
O3D—C11B—C10B—C9B	−154.2 (6)	C16C—C17C—C18C—C19C	0.0
C13B—C8B—C9B—C10B	1.8 (6)	C17C—C18C—C19C—C20C	0.0
C6B—C8B—C9B—C10B	−176.4 (4)	C18C—C19C—C20C—C15C	0.0
C11B—C10B—C9B—C8B	−0.8 (7)	C16C—C15C—C20C—C19C	0.0
O1A—C2A—N1A—N2A	−175.8 (3)	C14C—C15C—C20C—C19C	−149.9 (12)
C1A—C2A—N1A—N2A	5.0 (4)	O4C—C14C—O3C—C11A	29 (2)
O1A—C2A—N1A—C6A	−5.8 (5)	C15C—C14C—O3C—C11A	151.5 (11)
C1A—C2A—N1A—C6A	175.1 (3)	C12A—C11A—O3C—C14C	−132.4 (13)
C7A—C6A—N1A—C2A	55.1 (4)	C10A—C11A—O3C—C14C	50.7 (15)
C8A—C6A—N1A—C2A	−73.2 (4)	O4B—C14B—C15B—C16B	−175.2 (9)
S1A—C6A—N1A—C2A	168.7 (2)	O3B—C14B—C15B—C16B	8.9 (10)
C7A—C6A—N1A—N2A	−134.7 (3)	O4B—C14B—C15B—C20B	3.8 (13)
C8A—C6A—N1A—N2A	97.0 (3)	O3B—C14B—C15B—C20B	−172.2 (6)
S1A—C6A—N1A—N2A	−21.0 (3)	C20B—C15B—C16B—C17B	0.0
N3A—C3A—N2A—N1A	178.5 (2)	C14B—C15B—C16B—C17B	178.9 (8)
S1A—C3A—N2A—N1A	−1.5 (3)	C15B—C16B—C17B—C18B	0.0
C2A—N1A—N2A—C3A	−173.3 (3)	C16B—C17B—C18B—C19B	0.0
C6A—N1A—N2A—C3A	15.9 (3)	C17B—C18B—C19B—C20B	0.0
O2A—C4A—N3A—C3A	3.5 (5)	C18B—C19B—C20B—C15B	0.0
C5A—C4A—N3A—C3A	−175.3 (3)	C16B—C15B—C20B—C19B	0.0
N2A—C3A—N3A—C4A	−175.4 (3)	C14B—C15B—C20B—C19B	−178.9 (7)
S1A—C3A—N3A—C4A	4.6 (4)	O4B—C14B—O3B—C11B	4.4 (12)
O1B—C2B—N1B—N2B	−175.6 (3)	C15B—C14B—O3B—C11B	−179.4 (6)
C1B—C2B—N1B—N2B	3.8 (5)	C12B—C11B—O3B—C14B	−110.0 (7)
O1B—C2B—N1B—C6B	−8.8 (5)	C10B—C11B—O3B—C14B	85.6 (8)
C1B—C2B—N1B—C6B	170.5 (3)	O4D—C14D—C15D—C16D	−5 (2)
C8B—C6B—N1B—C2B	−67.7 (4)	O3D—C14D—C15D—C16D	173.9 (11)
C7B—C6B—N1B—C2B	61.6 (4)	O4D—C14D—C15D—C20D	175.6 (14)
S1B—C6B—N1B—C2B	175.6 (3)	O3D—C14D—C15D—C20D	−5.3 (17)
C8B—C6B—N1B—N2B	99.4 (3)	C20D—C15D—C16D—C17D	0.0
C7B—C6B—N1B—N2B	−131.4 (3)	C14D—C15D—C16D—C17D	−179.2 (15)
S1B—C6B—N1B—N2B	−17.4 (3)	C15D—C16D—C17D—C18D	0.0
N3B—C3B—N2B—N1B	−178.7 (3)	C16D—C17D—C18D—C19D	0.0
S1B—C3B—N2B—N1B	0.3 (3)	C17D—C18D—C19D—C20D	0.0
C2B—N1B—N2B—C3B	179.9 (3)	C18D—C19D—C20D—C15D	0.0
C6B—N1B—N2B—C3B	12.3 (4)	C16D—C15D—C20D—C19D	0.0
O2B—C4B—N3B—C3B	4.4 (5)	C14D—C15D—C20D—C19D	179.2 (15)
C5B—C4B—N3B—C3B	−174.5 (3)	O4D—C14D—O3D—C11B	−4.6 (19)
N2B—C3B—N3B—C4B	−171.1 (3)	C15D—C14D—O3D—C11B	176.4 (11)
S1B—C3B—N3B—C4B	10.0 (4)	C12B—C11B—O3D—C14D	110.4 (10)
N2A—C3A—S1A—C6A	−9.6 (2)	C10B—C11B—O3D—C14D	−94.0 (10)

Hydrogen-bond geometry (Å, º)

Cg2, Cg3 and Cg6 are the centroids of the C8A–C13A, C15A–C20A and C8B–C13B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3A···O1B^i	0.84 (4)	1.96 (3)	2.792 (4)	175 (3)
N3B—H3B···O1A	0.84 (4)	1.99 (5)	2.801 (4)	163 (4)
C5A—H5A2···O1B^i	0.96	2.59	3.226 (5)	124
C7A—H7A2···O2A^ii	0.96	2.54	3.482 (5)	168
C9B—H9B···O2B^iii	0.93	2.58	3.303 (5)	135
C5B—H5B1···O4A^iv	0.96	2.59	3.50 (2)	158
C5B—H5B1···O4C^iv	0.96	2.45	3.395 (17)	166
C12A—H12A···O4C^iv	0.93	2.58	3.211 (15)	125
C17B—H17B···Cg2^v	0.93	2.91	3.664 (8)	139
C17C—H17C···Cg6^v	0.93	2.98	3.776 (10)	145
C20C—H20C···Cg3^vi	0.93	2.64	3.521 (11)	159

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

4-(5-Acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl 2-methylpropanoate 0.25-hydrate (II)

Crystal data

C17H21N3O4S·0.25H2O	Z = 4
Mr = 367.93	F(000) = 778
Triclinic, P1	Dx = 1.307 Mg m^−3
a = 6.7802 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 17.2671 (4) Å	Cell parameters from 7680 reflections
c = 17.3089 (4) Å	θ = 2.4–25.5°
α = 108.224 (1)°	µ = 0.20 mm^−1
β = 99.084 (1)°	T = 293 K
γ = 96.720 (1)°	BLOCK, colourless
V = 1870.50 (7) Å^3	0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	7680 independent reflections
Radiation source: fine-focus sealed tube	5737 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω and φ scans	θmax = 26.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −7→8
Tmin = 0.660, Tmax = 0.746	k = −21→21
27060 measured reflections	l = −21→21

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)] = 0.053	Hydrogen site location: mixed
wR(F^2) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0901P)^2 + 0.734P] where P = (Fo^2 + 2Fc^2)/3
7680 reflections	(Δ/σ)max = 0.002
525 parameters	Δρmax = 0.48 e Å^−3
242 restraints	Δρmin = −0.38 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C10B	0.6406 (7)	0.1228 (2)	0.0560 (2)	0.1066 (13)
H10B	0.6521	0.0767	0.0124	0.128*
C11B	0.4800 (6)	0.1636 (3)	0.0486 (2)	0.1023 (12)
C12B	0.4677 (5)	0.2347 (2)	0.1099 (2)	0.0826 (9)
H12B	0.3620	0.2633	0.1030	0.099*
C13B	0.6142 (4)	0.26296 (18)	0.18174 (17)	0.0650 (7)
H13B	0.6094	0.3123	0.2227	0.078*
C1B	0.6525 (4)	0.36366 (16)	0.43978 (17)	0.0646 (7)
H1B1	0.5739	0.3916	0.4095	0.097*
H1B2	0.7689	0.4020	0.4766	0.097*
H1B3	0.5709	0.3422	0.4715	0.097*
C1A	0.7780 (4)	0.59164 (14)	0.45336 (16)	0.0571 (6)
H1A1	0.8151	0.5379	0.4347	0.086*
H1A2	0.6334	0.5865	0.4382	0.086*
H1A3	0.8207	0.6154	0.5127	0.086*
C2A	0.8791 (4)	0.64657 (13)	0.41369 (14)	0.0474 (5)
C2B	0.7206 (4)	0.29410 (15)	0.38025 (15)	0.0528 (6)
C3A	0.7214 (3)	0.82955 (12)	0.50833 (13)	0.0411 (5)
C3B	1.0722 (3)	0.40326 (13)	0.31134 (13)	0.0420 (5)
C4A	0.6056 (4)	0.95076 (14)	0.59064 (16)	0.0562 (6)
C4B	1.3254 (4)	0.49275 (15)	0.27918 (15)	0.0517 (5)
C5A	0.4525 (5)	0.97664 (17)	0.6418 (2)	0.0774 (8)
H5A1	0.4990	1.0326	0.6787	0.116*
H5A2	0.4339	0.9407	0.6736	0.116*
H5A3	0.3259	0.9732	0.6060	0.116*
C5B	1.3775 (4)	0.57778 (17)	0.27520 (19)	0.0656 (7)
H5B1	1.5152	0.5870	0.2685	0.098*
H5B2	1.3627	0.6181	0.3257	0.098*
H5B3	1.2880	0.5828	0.2289	0.098*
C6B	0.9311 (4)	0.25124 (13)	0.27334 (14)	0.0477 (5)
C6A	0.9260 (3)	0.78654 (13)	0.39637 (14)	0.0440 (5)
C7A	1.1542 (4)	0.79518 (16)	0.40080 (18)	0.0608 (6)
H7A1	1.2227	0.8052	0.4569	0.091*
H7A2	1.1997	0.8407	0.3836	0.091*
H7A3	1.1839	0.7450	0.3648	0.091*
C7B	1.0076 (5)	0.18272 (16)	0.30150 (18)	0.0659 (7)
H7B1	1.0912	0.2066	0.3563	0.099*
H7B2	1.0858	0.1542	0.2637	0.099*
H7B3	0.8940	0.1443	0.3022	0.099*
C8B	0.7685 (4)	0.21984 (14)	0.19451 (15)	0.0530 (6)
C8A	0.7970 (3)	0.76385 (13)	0.30896 (13)	0.0435 (5)
C9A	0.8586 (4)	0.71431 (17)	0.23993 (16)	0.0621 (6)
H9A	0.9834	0.6973	0.2465	0.075*
C9B	0.7846 (6)	0.1514 (2)	0.1291 (2)	0.0855 (10)
H9B	0.8940	0.1244	0.1346	0.103*
C10A	0.7363 (5)	0.69025 (18)	0.16185 (17)	0.0704 (8)
H10A	0.7798	0.6576	0.1161	0.085*
C11A	0.5527 (4)	0.71394 (18)	0.15148 (16)	0.0634 (7)
C12A	0.4859 (4)	0.76212 (17)	0.21818 (16)	0.0623 (6)
H12A	0.3599	0.7781	0.2108	0.075*
C13A	0.6080 (4)	0.78648 (15)	0.29646 (15)	0.0523 (5)
H13A	0.5626	0.8188	0.3418	0.063*
C14A	0.2528 (5)	0.6466 (2)	0.04872 (17)	0.0773 (9)
C15A	0.1621 (6)	0.6282 (2)	−0.04174 (18)	0.0909 (11)
H15A	0.2016	0.6777	−0.0559	0.109*
C17A	0.2475 (9)	0.5587 (3)	−0.0944 (3)	0.1381 (18)
H17D	0.1983	0.5081	−0.0860	0.207*
H17E	0.3930	0.5707	−0.0789	0.207*
H17F	0.2059	0.5528	−0.1519	0.207*
C16A	−0.0658 (7)	0.6106 (3)	−0.0561 (2)	0.1227 (16)
H16D	−0.1225	0.6019	−0.1132	0.184*
H16E	−0.1123	0.6567	−0.0209	0.184*
H16F	−0.1081	0.5618	−0.0432	0.184*
N1B	0.8656 (3)	0.31381 (11)	0.34072 (11)	0.0465 (4)
N1A	0.8489 (3)	0.72603 (10)	0.43526 (11)	0.0431 (4)
N2A	0.7133 (3)	0.75104 (10)	0.48764 (11)	0.0432 (4)
N2B	0.9297 (3)	0.39715 (11)	0.35052 (11)	0.0442 (4)
N3B	1.1558 (3)	0.47934 (11)	0.31041 (11)	0.0463 (4)
H3B	1.0984	0.5209	0.3305	0.056*
N3A	0.6051 (3)	0.86705 (11)	0.56172 (11)	0.0462 (4)
H3A	0.5258	0.8359	0.5784	0.055*
O1B	0.6499 (3)	0.22122 (11)	0.36685 (13)	0.0733 (6)
O1A	0.9864 (3)	0.62179 (10)	0.36345 (12)	0.0633 (5)
O2A	0.7210 (4)	0.99870 (11)	0.57378 (15)	0.0877 (7)
O2B	1.4220 (3)	0.43814 (12)	0.25612 (14)	0.0745 (5)
O3A	0.4407 (4)	0.69246 (15)	0.07026 (11)	0.0851 (7)
O4A	0.1729 (4)	0.62528 (18)	0.09728 (14)	0.1077 (9)
S1A	0.88298 (9)	0.88522 (3)	0.46752 (4)	0.04905 (17)
S1B	1.15307 (10)	0.31302 (4)	0.25781 (4)	0.05540 (19)
C14B	0.1788 (9)	0.0980 (5)	−0.0412 (4)	0.1041 (19)	0.723 (5)
C15B	0.0485 (11)	0.0684 (5)	−0.1256 (5)	0.097 (2)	0.723 (5)
H15B	−0.0377	0.0159	−0.1331	0.117*	0.723 (5)
C16B	−0.0847 (12)	0.1334 (5)	−0.1207 (5)	0.143 (3)	0.723 (5)
H16A	−0.1765	0.1199	−0.1732	0.214*	0.723 (5)
H16B	−0.1609	0.1350	−0.0781	0.214*	0.723 (5)
H16C	−0.0015	0.1866	−0.1077	0.214*	0.723 (5)
C17B	0.1577 (13)	0.0551 (5)	−0.1955 (4)	0.115 (2)	0.723 (5)
H17A	0.0609	0.0361	−0.2473	0.173*	0.723 (5)
H17B	0.2408	0.1062	−0.1901	0.173*	0.723 (5)
H17C	0.2417	0.0143	−0.1943	0.173*	0.723 (5)
O3B	0.3507 (7)	0.1413 (3)	−0.0316 (3)	0.1161 (16)	0.723 (5)
O4B	0.1403 (8)	0.0725 (5)	0.0133 (4)	0.171 (3)	0.723 (5)
C14'	0.262 (2)	0.1068 (12)	−0.0760 (10)	0.104 (4)	0.277 (5)
C15'	0.056 (3)	0.0920 (18)	−0.1333 (12)	0.117 (6)	0.277 (5)
H15'	0.0300	0.1483	−0.1257	0.140*	0.277 (5)
C16'	−0.155 (3)	0.0433 (17)	−0.1396 (14)	0.177 (8)	0.277 (5)
H16G	−0.1870	0.0565	−0.0853	0.266*	0.277 (5)
H16H	−0.2556	0.0582	−0.1755	0.266*	0.277 (5)
H16I	−0.1551	−0.0150	−0.1619	0.266*	0.277 (5)
C17'	0.054 (4)	0.0580 (17)	−0.2240 (12)	0.138 (8)	0.277 (5)
H17G	−0.0814	0.0508	−0.2550	0.208*	0.277 (5)
H17H	0.1433	0.0958	−0.2388	0.208*	0.277 (5)
H17I	0.0985	0.0055	−0.2365	0.208*	0.277 (5)
O3B'	0.275 (2)	0.1204 (10)	0.0005 (7)	0.138 (4)	0.277 (5)
O4B'	0.418 (2)	0.1056 (11)	−0.1017 (8)	0.163 (6)	0.277 (5)
O1	−0.348 (3)	−0.0897 (8)	−0.1929 (9)	0.240 (5)*	0.5
H1A	−0.36 (3)	−0.138 (5)	−0.231 (7)	0.288*	0.5
H1B	−0.33 (3)	−0.100 (10)	−0.146 (5)	0.288*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C10B	0.116 (3)	0.092 (3)	0.081 (2)	0.028 (2)	0.005 (2)	−0.0110 (19)
C11B	0.090 (3)	0.110 (3)	0.073 (2)	0.010 (2)	−0.0138 (18)	0.001 (2)
C12B	0.0668 (19)	0.102 (2)	0.0749 (19)	0.0302 (17)	0.0075 (15)	0.0218 (18)
C13B	0.0642 (16)	0.0689 (17)	0.0586 (15)	0.0225 (13)	0.0118 (12)	0.0135 (13)
C1B	0.0747 (17)	0.0555 (15)	0.0730 (17)	0.0097 (13)	0.0389 (14)	0.0239 (13)
C1A	0.0748 (16)	0.0351 (11)	0.0678 (15)	0.0116 (11)	0.0221 (13)	0.0220 (11)
C2A	0.0535 (13)	0.0343 (11)	0.0538 (12)	0.0069 (9)	0.0090 (11)	0.0157 (9)
C2B	0.0623 (15)	0.0467 (13)	0.0574 (13)	0.0080 (11)	0.0211 (11)	0.0249 (11)
C3A	0.0437 (11)	0.0347 (10)	0.0442 (11)	0.0033 (8)	0.0052 (9)	0.0153 (8)
C3B	0.0472 (12)	0.0401 (11)	0.0413 (10)	0.0118 (9)	0.0097 (9)	0.0157 (9)
C4A	0.0701 (16)	0.0366 (12)	0.0609 (14)	0.0078 (11)	0.0166 (12)	0.0142 (10)
C4B	0.0469 (13)	0.0553 (14)	0.0533 (13)	0.0037 (11)	0.0098 (10)	0.0210 (11)
C5A	0.099 (2)	0.0481 (15)	0.092 (2)	0.0249 (15)	0.0407 (18)	0.0182 (14)
C5B	0.0621 (16)	0.0624 (16)	0.0813 (18)	0.0029 (12)	0.0224 (14)	0.0360 (14)
C6B	0.0559 (13)	0.0365 (11)	0.0554 (13)	0.0132 (10)	0.0182 (10)	0.0172 (10)
C6A	0.0427 (11)	0.0345 (10)	0.0570 (12)	0.0038 (8)	0.0137 (10)	0.0180 (9)
C7A	0.0438 (13)	0.0513 (14)	0.0886 (18)	0.0026 (10)	0.0184 (12)	0.0252 (13)
C7B	0.0865 (19)	0.0470 (14)	0.0730 (17)	0.0270 (13)	0.0168 (14)	0.0268 (12)
C8B	0.0578 (14)	0.0434 (12)	0.0559 (13)	0.0124 (10)	0.0138 (11)	0.0119 (10)
C8A	0.0469 (12)	0.0365 (10)	0.0525 (12)	0.0031 (9)	0.0166 (10)	0.0207 (9)
C9A	0.0616 (15)	0.0651 (16)	0.0653 (16)	0.0164 (12)	0.0255 (13)	0.0219 (13)
C9B	0.093 (2)	0.0699 (19)	0.076 (2)	0.0291 (17)	0.0075 (17)	0.0004 (16)
C10A	0.086 (2)	0.0720 (18)	0.0532 (15)	0.0108 (15)	0.0282 (14)	0.0155 (13)
C11A	0.0727 (18)	0.0674 (16)	0.0514 (14)	−0.0018 (13)	0.0130 (12)	0.0269 (12)
C12A	0.0606 (15)	0.0692 (17)	0.0592 (15)	0.0112 (13)	0.0083 (12)	0.0267 (13)
C13A	0.0548 (14)	0.0513 (13)	0.0532 (13)	0.0116 (11)	0.0147 (11)	0.0186 (10)
C14A	0.095 (2)	0.081 (2)	0.0536 (15)	−0.0028 (17)	0.0060 (15)	0.0302 (15)
C15A	0.117 (3)	0.092 (2)	0.0532 (16)	−0.005 (2)	0.0021 (17)	0.0273 (16)
C17A	0.174 (5)	0.154 (5)	0.076 (3)	0.041 (4)	0.028 (3)	0.019 (3)
C16A	0.130 (4)	0.154 (4)	0.071 (2)	0.014 (3)	−0.008 (2)	0.039 (2)
N1B	0.0592 (11)	0.0358 (9)	0.0488 (10)	0.0088 (8)	0.0192 (9)	0.0160 (8)
N1A	0.0471 (10)	0.0328 (9)	0.0525 (10)	0.0058 (7)	0.0130 (8)	0.0180 (8)
N2A	0.0491 (10)	0.0340 (9)	0.0493 (10)	0.0057 (7)	0.0127 (8)	0.0173 (8)
N2B	0.0555 (11)	0.0366 (9)	0.0461 (9)	0.0097 (8)	0.0189 (8)	0.0171 (8)
N3B	0.0512 (11)	0.0400 (10)	0.0536 (10)	0.0098 (8)	0.0201 (8)	0.0188 (8)
N3A	0.0525 (11)	0.0343 (9)	0.0537 (10)	0.0056 (8)	0.0151 (8)	0.0164 (8)
O1B	0.0928 (14)	0.0464 (10)	0.0925 (14)	0.0058 (9)	0.0455 (11)	0.0293 (9)
O1A	0.0766 (12)	0.0427 (9)	0.0826 (12)	0.0184 (8)	0.0391 (10)	0.0242 (8)
O2A	0.1157 (17)	0.0349 (9)	0.1144 (17)	0.0019 (10)	0.0567 (14)	0.0157 (10)
O2B	0.0606 (11)	0.0644 (12)	0.1115 (16)	0.0192 (9)	0.0414 (11)	0.0334 (11)
O3A	0.0955 (16)	0.1057 (17)	0.0484 (10)	−0.0107 (13)	0.0080 (10)	0.0317 (11)
O4A	0.1061 (19)	0.139 (2)	0.0681 (14)	−0.0272 (16)	−0.0003 (13)	0.0480 (15)
S1A	0.0540 (3)	0.0317 (3)	0.0599 (3)	−0.0010 (2)	0.0144 (3)	0.0152 (2)
S1B	0.0551 (4)	0.0462 (3)	0.0695 (4)	0.0163 (3)	0.0258 (3)	0.0170 (3)
C14B	0.076 (3)	0.140 (5)	0.077 (3)	0.007 (3)	0.012 (3)	0.016 (3)
C15B	0.087 (4)	0.096 (5)	0.092 (4)	−0.003 (3)	−0.015 (3)	0.031 (3)
C16B	0.119 (5)	0.144 (6)	0.183 (7)	0.049 (5)	0.010 (5)	0.080 (5)
C17B	0.143 (7)	0.097 (4)	0.082 (4)	−0.004 (5)	0.015 (4)	0.010 (3)
O3B	0.096 (3)	0.168 (4)	0.060 (2)	−0.020 (3)	−0.009 (2)	0.033 (2)
O4B	0.118 (4)	0.243 (7)	0.130 (4)	−0.024 (4)	0.014 (3)	0.059 (4)
C14'	0.104 (7)	0.121 (7)	0.085 (6)	−0.012 (6)	−0.005 (6)	0.055 (6)
C15'	0.093 (8)	0.127 (9)	0.098 (8)	0.016 (8)	−0.002 (7)	0.006 (8)
C16'	0.101 (11)	0.231 (17)	0.143 (13)	0.007 (12)	0.008 (10)	0.001 (13)
C17'	0.135 (15)	0.140 (13)	0.107 (13)	−0.017 (12)	−0.009 (11)	0.027 (11)
O3B'	0.114 (8)	0.175 (8)	0.086 (6)	−0.052 (7)	−0.019 (6)	0.036 (6)
O4B'	0.122 (9)	0.242 (14)	0.130 (10)	0.053 (9)	0.005 (8)	0.071 (9)

Geometric parameters (Å, º)

C10B—C11B	1.375 (5)	C8A—C13A	1.387 (3)
C10B—C9B	1.381 (5)	C8A—C9A	1.391 (3)
C10B—H10B	0.9300	C9A—C10A	1.379 (4)
C11B—C12B	1.370 (5)	C9A—H9A	0.9300
C11B—O3B	1.430 (5)	C9B—H9B	0.9300
C11B—O3B'	1.476 (11)	C10A—C11A	1.357 (4)
C12B—C13B	1.374 (4)	C10A—H10A	0.9300
C12B—H12B	0.9300	C11A—C12A	1.373 (4)
C13B—C8B	1.382 (4)	C11A—O3A	1.401 (3)
C13B—H13B	0.9300	C12A—C13A	1.381 (3)
C1B—C2B	1.491 (3)	C12A—H12A	0.9300
C1B—H1B1	0.9600	C13A—H13A	0.9300
C1B—H1B2	0.9600	C14A—O4A	1.195 (4)
C1B—H1B3	0.9600	C14A—O3A	1.348 (4)
C1A—C2A	1.498 (3)	C14A—C15A	1.507 (4)
C1A—H1A1	0.9600	C15A—C17A	1.501 (6)
C1A—H1A2	0.9600	C15A—C16A	1.505 (6)
C1A—H1A3	0.9600	C15A—H15A	0.9800
C2A—O1A	1.228 (3)	C17A—H17D	0.9600
C2A—N1A	1.354 (3)	C17A—H17E	0.9600
C2B—O1B	1.228 (3)	C17A—H17F	0.9600
C2B—N1B	1.353 (3)	C16A—H16D	0.9600
C3A—N2A	1.281 (3)	C16A—H16E	0.9600
C3A—N3A	1.368 (3)	C16A—H16F	0.9600
C3A—S1A	1.745 (2)	N1B—N2B	1.402 (2)
C3B—N2B	1.278 (3)	N1A—N2A	1.401 (2)
C3B—N3B	1.374 (3)	N3B—H3B	0.8600
C3B—S1B	1.745 (2)	N3A—H3A	0.8600
C4A—O2A	1.206 (3)	C14B—O4B	1.209 (8)
C4A—N3A	1.373 (3)	C14B—O3B	1.266 (7)
C4A—C5A	1.487 (4)	C14B—C15B	1.482 (8)
C4B—O2B	1.212 (3)	C15B—C17B	1.487 (9)
C4B—N3B	1.372 (3)	C15B—C16B	1.511 (9)
C4B—C5B	1.495 (4)	C15B—H15B	0.9800
C5A—H5A1	0.9600	C16B—H16A	0.9600
C5A—H5A2	0.9600	C16B—H16B	0.9600
C5A—H5A3	0.9600	C16B—H16C	0.9600
C5B—H5B1	0.9600	C17B—H17A	0.9600
C5B—H5B2	0.9600	C17B—H17B	0.9600
C5B—H5B3	0.9600	C17B—H17C	0.9600
C6B—N1B	1.487 (3)	C14'—O4B'	1.212 (15)
C6B—C8B	1.514 (3)	C14'—O3B'	1.256 (14)
C6B—C7B	1.527 (3)	C14'—C15'	1.522 (16)
C6B—S1B	1.846 (2)	C15'—C17'	1.491 (15)
C6A—N1A	1.497 (3)	C15'—C16'	1.544 (16)
C6A—C7A	1.524 (3)	C15'—H15'	0.9800
C6A—C8A	1.529 (3)	C16'—H16G	0.9600
C6A—S1A	1.850 (2)	C16'—H16H	0.9600
C7A—H7A1	0.9600	C16'—H16I	0.9600
C7A—H7A2	0.9600	C17'—H17G	0.9600
C7A—H7A3	0.9600	C17'—H17H	0.9600
C7B—H7B1	0.9600	C17'—H17I	0.9600
C7B—H7B2	0.9600	O1—H1A	0.87 (2)
C7B—H7B3	0.9600	O1—H1B	0.88 (2)
C8B—C9B	1.386 (4)
C11B—C10B—C9B	118.8 (3)	C9A—C10A—H10A	119.9
C11B—C10B—H10B	120.6	C10A—C11A—C12A	120.8 (2)
C9B—C10B—H10B	120.6	C10A—C11A—O3A	117.9 (3)
C12B—C11B—C10B	121.3 (3)	C12A—C11A—O3A	121.2 (3)
C12B—C11B—O3B	119.4 (4)	C11A—C12A—C13A	119.1 (3)
C10B—C11B—O3B	117.8 (4)	C11A—C12A—H12A	120.4
C12B—C11B—O3B'	110.3 (7)	C13A—C12A—H12A	120.4
C10B—C11B—O3B'	122.6 (8)	C12A—C13A—C8A	121.5 (2)
C11B—C12B—C13B	118.9 (3)	C12A—C13A—H13A	119.3
C11B—C12B—H12B	120.5	C8A—C13A—H13A	119.3
C13B—C12B—H12B	120.5	O4A—C14A—O3A	122.5 (3)
C12B—C13B—C8B	121.5 (3)	O4A—C14A—C15A	126.2 (3)
C12B—C13B—H13B	119.2	O3A—C14A—C15A	111.3 (3)
C8B—C13B—H13B	119.2	C17A—C15A—C16A	112.9 (4)
C2B—C1B—H1B1	109.5	C17A—C15A—C14A	109.7 (3)
C2B—C1B—H1B2	109.5	C16A—C15A—C14A	110.0 (3)
H1B1—C1B—H1B2	109.5	C17A—C15A—H15A	108.0
C2B—C1B—H1B3	109.5	C16A—C15A—H15A	108.0
H1B1—C1B—H1B3	109.5	C14A—C15A—H15A	108.0
H1B2—C1B—H1B3	109.5	C15A—C17A—H17D	109.5
C2A—C1A—H1A1	109.5	C15A—C17A—H17E	109.5
C2A—C1A—H1A2	109.5	H17D—C17A—H17E	109.5
H1A1—C1A—H1A2	109.5	C15A—C17A—H17F	109.5
C2A—C1A—H1A3	109.5	H17D—C17A—H17F	109.5
H1A1—C1A—H1A3	109.5	H17E—C17A—H17F	109.5
H1A2—C1A—H1A3	109.5	C15A—C16A—H16D	109.5
O1A—C2A—N1A	120.2 (2)	C15A—C16A—H16E	109.5
O1A—C2A—C1A	122.3 (2)	H16D—C16A—H16E	109.5
N1A—C2A—C1A	117.5 (2)	C15A—C16A—H16F	109.5
O1B—C2B—N1B	120.3 (2)	H16D—C16A—H16F	109.5
O1B—C2B—C1B	122.2 (2)	H16E—C16A—H16F	109.5
N1B—C2B—C1B	117.5 (2)	C2B—N1B—N2B	119.31 (18)
N2A—C3A—N3A	119.36 (19)	C2B—N1B—C6B	122.96 (18)
N2A—C3A—S1A	118.46 (17)	N2B—N1B—C6B	116.47 (16)
N3A—C3A—S1A	122.18 (15)	C2A—N1A—N2A	119.05 (17)
N2B—C3B—N3B	120.21 (19)	C2A—N1A—C6A	123.88 (18)
N2B—C3B—S1B	118.48 (16)	N2A—N1A—C6A	116.36 (16)
N3B—C3B—S1B	121.29 (16)	C3A—N2A—N1A	110.01 (17)
O2A—C4A—N3A	121.3 (2)	C3B—N2B—N1B	109.86 (17)
O2A—C4A—C5A	123.4 (2)	C4B—N3B—C3B	123.7 (2)
N3A—C4A—C5A	115.3 (2)	C4B—N3B—H3B	118.1
O2B—C4B—N3B	121.1 (2)	C3B—N3B—H3B	118.1
O2B—C4B—C5B	123.8 (2)	C3A—N3A—C4A	124.8 (2)
N3B—C4B—C5B	115.2 (2)	C3A—N3A—H3A	117.6
C4A—C5A—H5A1	109.5	C4A—N3A—H3A	117.6
C4A—C5A—H5A2	109.5	C14A—O3A—C11A	119.9 (2)
H5A1—C5A—H5A2	109.5	C3A—S1A—C6A	89.58 (10)
C4A—C5A—H5A3	109.5	C3B—S1B—C6B	89.29 (10)
H5A1—C5A—H5A3	109.5	O4B—C14B—O3B	119.7 (6)
H5A2—C5A—H5A3	109.5	O4B—C14B—C15B	122.5 (7)
C4B—C5B—H5B1	109.5	O3B—C14B—C15B	116.8 (6)
C4B—C5B—H5B2	109.5	C14B—C15B—C17B	115.7 (6)
H5B1—C5B—H5B2	109.5	C14B—C15B—C16B	102.7 (6)
C4B—C5B—H5B3	109.5	C17B—C15B—C16B	113.7 (7)
H5B1—C5B—H5B3	109.5	C14B—C15B—H15B	108.1
H5B2—C5B—H5B3	109.5	C17B—C15B—H15B	108.1
N1B—C6B—C8B	111.11 (18)	C16B—C15B—H15B	108.1
N1B—C6B—C7B	112.30 (19)	C15B—C16B—H16A	109.5
C8B—C6B—C7B	114.0 (2)	C15B—C16B—H16B	109.5
N1B—C6B—S1B	101.72 (14)	H16A—C16B—H16B	109.5
C8B—C6B—S1B	109.87 (16)	C15B—C16B—H16C	109.5
C7B—C6B—S1B	107.00 (18)	H16A—C16B—H16C	109.5
N1A—C6A—C7A	112.66 (18)	H16B—C16B—H16C	109.5
N1A—C6A—C8A	108.50 (16)	C15B—C17B—H17A	109.5
C7A—C6A—C8A	114.9 (2)	C15B—C17B—H17B	109.5
N1A—C6A—S1A	101.53 (14)	H17A—C17B—H17B	109.5
C7A—C6A—S1A	106.51 (15)	C15B—C17B—H17C	109.5
C8A—C6A—S1A	111.94 (15)	H17A—C17B—H17C	109.5
C6A—C7A—H7A1	109.5	H17B—C17B—H17C	109.5
C6A—C7A—H7A2	109.5	C14B—O3B—C11B	115.8 (5)
H7A1—C7A—H7A2	109.5	O4B'—C14'—O3B'	117.3 (15)
C6A—C7A—H7A3	109.5	O4B'—C14'—C15'	122.0 (15)
H7A1—C7A—H7A3	109.5	O3B'—C14'—C15'	120.7 (16)
H7A2—C7A—H7A3	109.5	C17'—C15'—C14'	115.4 (17)
C6B—C7B—H7B1	109.5	C17'—C15'—C16'	95.1 (17)
C6B—C7B—H7B2	109.5	C14'—C15'—C16'	134 (2)
H7B1—C7B—H7B2	109.5	C17'—C15'—H15'	102.9
C6B—C7B—H7B3	109.5	C14'—C15'—H15'	102.9
H7B1—C7B—H7B3	109.5	C16'—C15'—H15'	102.9
H7B2—C7B—H7B3	109.5	C15'—C16'—H16G	109.5
C13B—C8B—C9B	118.0 (3)	C15'—C16'—H16H	109.5
C13B—C8B—C6B	121.6 (2)	H16G—C16'—H16H	109.5
C9B—C8B—C6B	120.0 (2)	C15'—C16'—H16I	109.5
C13A—C8A—C9A	117.7 (2)	H16G—C16'—H16I	109.5
C13A—C8A—C6A	121.2 (2)	H16H—C16'—H16I	109.5
C9A—C8A—C6A	120.9 (2)	C15'—C17'—H17G	109.5
C10A—C9A—C8A	120.6 (3)	C15'—C17'—H17H	109.5
C10A—C9A—H9A	119.7	H17G—C17'—H17H	109.5
C8A—C9A—H9A	119.7	C15'—C17'—H17I	109.5
C10B—C9B—C8B	121.1 (3)	H17G—C17'—H17I	109.5
C10B—C9B—H9B	119.5	H17H—C17'—H17I	109.5
C8B—C9B—H9B	119.5	C14'—O3B'—C11B	111.7 (12)
C11A—C10A—C9A	120.3 (3)	H1A—O1—H1B	105 (3)
C11A—C10A—H10A	119.9
C9B—C10B—C11B—C12B	4.3 (7)	C7A—C6A—N1A—C2A	−54.8 (3)
C9B—C10B—C11B—O3B	170.4 (4)	C8A—C6A—N1A—C2A	73.6 (2)
C9B—C10B—C11B—O3B'	−146.4 (7)	S1A—C6A—N1A—C2A	−168.36 (17)
C10B—C11B—C12B—C13B	−3.3 (7)	C7A—C6A—N1A—N2A	134.9 (2)
O3B—C11B—C12B—C13B	−169.1 (4)	C8A—C6A—N1A—N2A	−96.7 (2)
O3B'—C11B—C12B—C13B	150.6 (7)	S1A—C6A—N1A—N2A	21.4 (2)
C11B—C12B—C13B—C8B	−2.4 (5)	N3A—C3A—N2A—N1A	−177.87 (17)
C12B—C13B—C8B—C9B	6.7 (5)	S1A—C3A—N2A—N1A	1.7 (2)
C12B—C13B—C8B—C6B	179.5 (3)	C2A—N1A—N2A—C3A	172.95 (19)
N1B—C6B—C8B—C13B	18.3 (3)	C6A—N1A—N2A—C3A	−16.3 (2)
C7B—C6B—C8B—C13B	146.5 (3)	N3B—C3B—N2B—N1B	178.38 (18)
S1B—C6B—C8B—C13B	−93.5 (3)	S1B—C3B—N2B—N1B	−0.3 (2)
N1B—C6B—C8B—C9B	−169.0 (3)	C2B—N1B—N2B—C3B	177.4 (2)
C7B—C6B—C8B—C9B	−40.9 (3)	C6B—N1B—N2B—C3B	−15.1 (3)
S1B—C6B—C8B—C9B	79.2 (3)	O2B—C4B—N3B—C3B	−5.9 (4)
N1A—C6A—C8A—C13A	80.1 (2)	C5B—C4B—N3B—C3B	173.3 (2)
C7A—C6A—C8A—C13A	−152.8 (2)	N2B—C3B—N3B—C4B	171.3 (2)
S1A—C6A—C8A—C13A	−31.1 (2)	S1B—C3B—N3B—C4B	−10.1 (3)
N1A—C6A—C8A—C9A	−94.9 (2)	N2A—C3A—N3A—C4A	177.7 (2)
C7A—C6A—C8A—C9A	32.2 (3)	S1A—C3A—N3A—C4A	−1.9 (3)
S1A—C6A—C8A—C9A	153.89 (19)	O2A—C4A—N3A—C3A	−4.3 (4)
C13A—C8A—C9A—C10A	1.2 (4)	C5A—C4A—N3A—C3A	174.5 (2)
C6A—C8A—C9A—C10A	176.4 (2)	O4A—C14A—O3A—C11A	2.6 (5)
C11B—C10B—C9B—C8B	0.3 (6)	C15A—C14A—O3A—C11A	−178.1 (3)
C13B—C8B—C9B—C10B	−5.6 (5)	C10A—C11A—O3A—C14A	121.9 (3)
C6B—C8B—C9B—C10B	−178.5 (3)	C12A—C11A—O3A—C14A	−62.3 (4)
C8A—C9A—C10A—C11A	−0.7 (4)	N2A—C3A—S1A—C6A	9.51 (18)
C9A—C10A—C11A—C12A	0.1 (4)	N3A—C3A—S1A—C6A	−170.93 (18)
C9A—C10A—C11A—O3A	175.8 (2)	N1A—C6A—S1A—C3A	−15.74 (14)
C10A—C11A—C12A—C13A	0.1 (4)	C7A—C6A—S1A—C3A	−133.82 (17)
O3A—C11A—C12A—C13A	−175.5 (2)	C8A—C6A—S1A—C3A	99.82 (15)
C11A—C12A—C13A—C8A	0.5 (4)	N2B—C3B—S1B—C6B	11.17 (18)
C9A—C8A—C13A—C12A	−1.1 (3)	N3B—C3B—S1B—C6B	−167.47 (18)
C6A—C8A—C13A—C12A	−176.2 (2)	N1B—C6B—S1B—C3B	−16.53 (14)
O4A—C14A—C15A—C17A	−101.7 (5)	C8B—C6B—S1B—C3B	101.25 (16)
O3A—C14A—C15A—C17A	79.1 (4)	C7B—C6B—S1B—C3B	−134.49 (17)
O4A—C14A—C15A—C16A	23.1 (6)	O4B—C14B—C15B—C17B	−139.6 (8)
O3A—C14A—C15A—C16A	−156.1 (3)	O3B—C14B—C15B—C17B	29.2 (10)
O1B—C2B—N1B—N2B	173.7 (2)	O4B—C14B—C15B—C16B	95.9 (9)
C1B—C2B—N1B—N2B	−6.5 (3)	O3B—C14B—C15B—C16B	−95.3 (8)
O1B—C2B—N1B—C6B	7.0 (4)	O4B—C14B—O3B—C11B	−6.2 (10)
C1B—C2B—N1B—C6B	−173.2 (2)	C15B—C14B—O3B—C11B	−175.3 (6)
C8B—C6B—N1B—C2B	71.5 (3)	C12B—C11B—O3B—C14B	−88.4 (7)
C7B—C6B—N1B—C2B	−57.5 (3)	C10B—C11B—O3B—C14B	105.3 (6)
S1B—C6B—N1B—C2B	−171.57 (18)	O4B'—C14'—C15'—C17'	13 (3)
C8B—C6B—N1B—N2B	−95.5 (2)	O3B'—C14'—C15'—C17'	−167 (2)
C7B—C6B—N1B—N2B	135.4 (2)	O4B'—C14'—C15'—C16'	139 (3)
S1B—C6B—N1B—N2B	21.4 (2)	O3B'—C14'—C15'—C16'	−41 (4)
O1A—C2A—N1A—N2A	175.0 (2)	O4B'—C14'—O3B'—C11B	22 (3)
C1A—C2A—N1A—N2A	−5.1 (3)	C15'—C14'—O3B'—C11B	−158.1 (18)
O1A—C2A—N1A—C6A	5.0 (3)	C12B—C11B—O3B'—C14'	125.5 (14)
C1A—C2A—N1A—C6A	−175.1 (2)	C10B—C11B—O3B'—C14'	−81.1 (17)

Hydrogen-bond geometry (Å, º)

Cg2 and Cg4 are the centroids of the C8B–C13B and C8A–C13A rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O4B^i	0.88 (11)	2.32 (10)	3.111 (16)	149 (12)
N3A—H3A···O1B^ii	0.86	1.99	2.842 (3)	171
N3B—H3B···O1A	0.86	1.94	2.792 (3)	171
C15B—H15B···O1	0.98	2.46	3.368 (19)	154
C7B—H7B2···O1^iii	0.96	2.49	3.434 (19)	168
C15A—H15A···Cg2^iv	0.98	2.99	3.959 (4)	168
C17B—H17B···Cg4^iv	0.96	2.98	3.864 (9)	153
C17′—H17H···Cg4^iv	0.96	2.93	3.81 (3)	154

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

4-(5-Acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl propionate (III)

Crystal data

C16H19N3O4S	Z = 4
Mr = 349.40	F(000) = 736
Triclinic, P1	Dx = 1.313 Mg m^−3
a = 11.4150 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.4021 (3) Å	Cell parameters from 7257 reflections
c = 13.2305 (3) Å	θ = 1.8–26.9°
α = 71.982 (1)°	µ = 0.21 mm^−1
β = 89.829 (1)°	T = 293 K
γ = 83.114 (1)°	Block, colourless
V = 1767.18 (8) Å^3	0.25 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	5869 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.022
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 26.4°, θmin = 1.6°
Tmin = 0.756, Tmax = 0.824	h = −14→14
26933 measured reflections	k = −15→15
7257 independent reflections	l = −16→16

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) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0486P)^2 + 0.4775P] where P = (Fo^2 + 2Fc^2)/3
7257 reflections	(Δ/σ)max = 0.012
451 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.57800 (12)	1.34448 (11)	0.74760 (12)	0.0525 (3)
H1A	0.620681	1.370276	0.786145	0.063*
O1B	0.30213 (13)	0.50078 (14)	0.84275 (14)	0.0854 (5)
O2A	0.73259 (12)	0.86411 (11)	0.91134 (11)	0.0707 (4)
C5A	0.51016 (19)	1.54430 (15)	0.65971 (18)	0.0696 (5)
H5A1	0.557477	1.576433	0.600418	0.104*
H5A2	0.545055	1.550089	0.723459	0.104*
H5A3	0.432011	1.585300	0.647905	0.104*
C5B	0.41647 (18)	0.3577 (2)	0.9822 (2)	0.0847 (7)
H5B1	0.440346	0.286150	0.969805	0.127*
H5B2	0.402035	0.344392	1.056366	0.127*
H5B3	0.477912	0.405929	0.961867	0.127*
C4B	0.30600 (16)	0.41497 (16)	0.91784 (16)	0.0595 (4)
C4A	0.50385 (16)	1.42199 (14)	0.67108 (15)	0.0545 (4)
C3B	0.09508 (14)	0.40749 (12)	0.90740 (12)	0.0430 (3)
C3A	0.58882 (13)	1.22853 (13)	0.76694 (12)	0.0443 (3)
C2B	−0.20340 (15)	0.38900 (14)	0.93581 (13)	0.0475 (4)
C2A	0.74122 (16)	0.96458 (16)	0.90086 (14)	0.0557 (4)
C1A	0.8399 (2)	1.0004 (2)	0.95195 (19)	0.0819 (7)
H1A1	0.894461	0.934423	0.987754	0.123*
H1A2	0.808622	1.036605	1.002461	0.123*
H1A3	0.879963	1.053137	0.898454	0.123*
C1B	−0.20176 (18)	0.30017 (18)	1.04232 (15)	0.0661 (5)
H1B1	−0.281171	0.286795	1.061371	0.099*
H1B2	−0.165756	0.326230	1.094501	0.099*
H1B3	−0.157297	0.230441	1.039480	0.099*
C6A	0.56363 (14)	1.02464 (13)	0.77881 (13)	0.0480 (4)
C6B	−0.08741 (14)	0.49848 (13)	0.78791 (12)	0.0439 (3)
C7B	−0.15459 (18)	0.61708 (14)	0.77098 (15)	0.0599 (5)
H7B1	−0.237776	0.613673	0.765099	0.090*
H7B2	−0.129831	0.669363	0.706902	0.090*
H7B3	−0.138429	0.642805	0.830298	0.090*
C7A	0.46982 (17)	0.97282 (17)	0.85428 (16)	0.0631 (5)
H7A1	0.498929	0.895550	0.894576	0.095*
H7A2	0.399801	0.973411	0.814005	0.095*
H7A3	0.451600	1.016824	0.901843	0.095*
C8A	0.60797 (14)	0.95904 (13)	0.70392 (13)	0.0467 (4)
C8B	−0.11842 (13)	0.44221 (13)	0.70592 (12)	0.0427 (3)
C13B	−0.11426 (16)	0.32545 (14)	0.73185 (13)	0.0504 (4)
H13B	−0.093842	0.280152	0.801309	0.060*
C9A	0.53636 (16)	0.89412 (15)	0.66959 (16)	0.0593 (4)
H9A	0.461151	0.886891	0.696048	0.071*
C12B	−0.13966 (17)	0.27416 (15)	0.65726 (14)	0.0555 (4)
H12B	−0.136280	0.195077	0.676341	0.067*
C10A	0.57469 (17)	0.83983 (15)	0.59663 (16)	0.0616 (5)
H10A	0.525298	0.797237	0.573355	0.074*
C11B	−0.16969 (15)	0.33979 (16)	0.55560 (14)	0.0545 (4)
C11A	0.68586 (16)	0.84921 (13)	0.55888 (14)	0.0520 (4)
C10B	−0.1753 (2)	0.45512 (18)	0.52740 (16)	0.0848 (7)
H10B	−0.196507	0.499665	0.457871	0.102*
C12A	0.75876 (17)	0.91397 (17)	0.59031 (16)	0.0606 (4)
H12A	0.834058	0.920341	0.563862	0.073*
C13A	0.71888 (16)	0.96928 (16)	0.66141 (15)	0.0588 (4)
H13A	0.767410	1.014739	0.681596	0.071*
C9B	−0.1494 (2)	0.50628 (16)	0.60244 (15)	0.0772 (7)
H9B	−0.152876	0.585410	0.582606	0.093*
C14B	−0.11985 (18)	0.23156 (17)	0.43963 (15)	0.0599 (4)
C14A	0.75675 (15)	0.84105 (14)	0.39311 (14)	0.0518 (4)
C15B	−0.1704 (2)	0.18925 (18)	0.35733 (16)	0.0677 (5)
H15A	−0.210289	0.253823	0.301650	0.081*
H15B	−0.228848	0.139518	0.389471	0.081*
C15A	0.81032 (18)	0.75962 (16)	0.33897 (16)	0.0637 (5)
H15C	0.759433	0.700728	0.345461	0.076*
H15D	0.885816	0.722948	0.373824	0.076*
C16A	0.8284 (2)	0.8183 (2)	0.22260 (18)	0.0888 (7)
H16A	0.753154	0.849116	0.186584	0.133*
H16B	0.867850	0.764059	0.191567	0.133*
H16C	0.875623	0.879079	0.215732	0.133*
C16B	−0.0785 (2)	0.1249 (2)	0.30835 (19)	0.0837 (7)
H16D	−0.022136	0.174521	0.273753	0.126*
H16E	−0.115993	0.098469	0.257153	0.126*
H16F	−0.038825	0.060581	0.362960	0.126*
N1B	0.20675 (12)	0.36478 (12)	0.95143 (11)	0.0508 (3)
H1B	0.214485	0.302221	1.003664	0.061*
N2B	0.00570 (12)	0.36683 (11)	0.95615 (10)	0.0462 (3)
N2A	0.66403 (12)	1.16162 (11)	0.83704 (11)	0.0489 (3)
N3A	0.66139 (12)	1.04853 (11)	0.83936 (11)	0.0495 (3)
N3B	−0.09860 (11)	0.42081 (11)	0.89767 (10)	0.0440 (3)
O1A	0.43966 (13)	1.39102 (11)	0.61613 (12)	0.0764 (4)
O2B	−0.29535 (10)	0.43215 (11)	0.88346 (10)	0.0582 (3)
O3A	0.72748 (12)	0.78457 (10)	0.49319 (10)	0.0604 (3)
O3B	−0.20361 (12)	0.29134 (13)	0.47883 (11)	0.0701 (4)
O4A	0.73852 (12)	0.94268 (10)	0.35619 (10)	0.0626 (3)
S1B	0.07220 (4)	0.51371 (4)	0.78475 (3)	0.05286 (12)
S1A	0.50357 (4)	1.16990 (4)	0.69416 (4)	0.05734 (14)
O4B	−0.0175 (6)	0.231 (2)	0.4588 (16)	0.081 (3)	0.68 (6)
O4B'	−0.030 (3)	0.184 (4)	0.491 (3)	0.081 (7)	0.32 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0511 (8)	0.0467 (7)	0.0612 (8)	−0.0057 (6)	−0.0134 (7)	−0.0190 (6)
O1B	0.0618 (9)	0.0804 (10)	0.0964 (11)	−0.0195 (7)	0.0056 (8)	0.0021 (9)
O2A	0.0677 (8)	0.0523 (7)	0.0770 (9)	0.0030 (6)	−0.0193 (7)	−0.0022 (6)
C5A	0.0723 (13)	0.0466 (10)	0.0855 (14)	−0.0058 (9)	−0.0078 (11)	−0.0147 (9)
C5B	0.0452 (11)	0.0925 (16)	0.1061 (18)	−0.0056 (10)	−0.0050 (11)	−0.0169 (14)
C4B	0.0485 (10)	0.0601 (11)	0.0697 (12)	−0.0076 (8)	0.0031 (9)	−0.0199 (9)
C4A	0.0515 (10)	0.0487 (9)	0.0608 (10)	−0.0051 (7)	−0.0054 (8)	−0.0140 (8)
C3B	0.0461 (9)	0.0391 (7)	0.0438 (8)	−0.0035 (6)	−0.0026 (7)	−0.0134 (6)
C3A	0.0400 (8)	0.0479 (8)	0.0456 (8)	−0.0048 (6)	−0.0033 (7)	−0.0156 (7)
C2B	0.0488 (9)	0.0551 (9)	0.0449 (8)	−0.0095 (7)	0.0018 (7)	−0.0236 (7)
C2A	0.0506 (10)	0.0570 (10)	0.0493 (9)	−0.0006 (8)	−0.0095 (8)	−0.0041 (8)
C1A	0.0676 (13)	0.0804 (14)	0.0819 (14)	−0.0057 (11)	−0.0356 (11)	−0.0035 (11)
C1B	0.0649 (12)	0.0773 (13)	0.0548 (10)	−0.0212 (10)	0.0086 (9)	−0.0141 (9)
C6A	0.0451 (9)	0.0445 (8)	0.0513 (9)	−0.0009 (7)	−0.0111 (7)	−0.0119 (7)
C6B	0.0473 (9)	0.0409 (8)	0.0405 (8)	−0.0045 (6)	−0.0030 (7)	−0.0085 (6)
C7B	0.0708 (12)	0.0451 (9)	0.0607 (11)	0.0037 (8)	−0.0053 (9)	−0.0161 (8)
C7A	0.0535 (10)	0.0682 (11)	0.0631 (11)	−0.0028 (9)	−0.0014 (9)	−0.0158 (9)
C8A	0.0465 (9)	0.0371 (7)	0.0527 (9)	−0.0011 (6)	−0.0079 (7)	−0.0100 (7)
C8B	0.0425 (8)	0.0427 (8)	0.0402 (8)	−0.0020 (6)	−0.0041 (6)	−0.0105 (6)
C13B	0.0623 (10)	0.0449 (8)	0.0412 (8)	−0.0051 (7)	0.0019 (7)	−0.0102 (7)
C9A	0.0492 (10)	0.0549 (10)	0.0800 (13)	−0.0093 (8)	0.0005 (9)	−0.0288 (9)
C12B	0.0661 (11)	0.0473 (9)	0.0572 (10)	−0.0131 (8)	0.0092 (8)	−0.0198 (8)
C10A	0.0603 (11)	0.0510 (10)	0.0809 (13)	−0.0124 (8)	−0.0052 (10)	−0.0292 (9)
C11B	0.0507 (9)	0.0642 (10)	0.0547 (10)	−0.0053 (8)	−0.0077 (8)	−0.0281 (8)
C11A	0.0603 (10)	0.0378 (8)	0.0555 (9)	0.0034 (7)	−0.0078 (8)	−0.0147 (7)
C10B	0.137 (2)	0.0612 (12)	0.0497 (11)	0.0032 (12)	−0.0350 (12)	−0.0127 (9)
C12A	0.0523 (10)	0.0676 (11)	0.0669 (11)	−0.0107 (8)	0.0035 (9)	−0.0269 (9)
C13A	0.0569 (10)	0.0612 (10)	0.0673 (11)	−0.0190 (8)	0.0005 (9)	−0.0286 (9)
C9B	0.130 (2)	0.0439 (9)	0.0515 (10)	−0.0020 (11)	−0.0264 (11)	−0.0090 (8)
C14B	0.0666 (12)	0.0665 (11)	0.0524 (10)	−0.0142 (10)	−0.0012 (9)	−0.0247 (9)
C14A	0.0477 (9)	0.0474 (9)	0.0609 (10)	0.0000 (7)	−0.0114 (8)	−0.0201 (8)
C15B	0.0867 (14)	0.0679 (12)	0.0568 (11)	−0.0235 (10)	−0.0046 (10)	−0.0265 (9)
C15A	0.0602 (11)	0.0600 (11)	0.0729 (12)	0.0093 (9)	−0.0081 (9)	−0.0296 (9)
C16A	0.0977 (18)	0.0957 (17)	0.0725 (14)	0.0254 (14)	−0.0056 (12)	−0.0390 (13)
C16B	0.1012 (18)	0.0925 (16)	0.0759 (14)	−0.0311 (14)	0.0079 (13)	−0.0458 (13)
N1B	0.0448 (7)	0.0487 (7)	0.0536 (8)	−0.0030 (6)	−0.0044 (6)	−0.0091 (6)
N2B	0.0455 (7)	0.0470 (7)	0.0415 (7)	−0.0025 (6)	−0.0039 (6)	−0.0083 (6)
N2A	0.0479 (8)	0.0493 (7)	0.0483 (7)	−0.0059 (6)	−0.0089 (6)	−0.0136 (6)
N3A	0.0488 (8)	0.0472 (7)	0.0497 (7)	0.0006 (6)	−0.0136 (6)	−0.0133 (6)
N3B	0.0425 (7)	0.0482 (7)	0.0390 (6)	−0.0044 (5)	−0.0033 (5)	−0.0108 (5)
O1A	0.0831 (10)	0.0533 (7)	0.0862 (10)	−0.0041 (7)	−0.0394 (8)	−0.0135 (7)
O2B	0.0444 (6)	0.0747 (8)	0.0602 (7)	−0.0063 (6)	−0.0045 (6)	−0.0281 (6)
O3A	0.0765 (8)	0.0419 (6)	0.0612 (7)	0.0042 (6)	−0.0027 (6)	−0.0177 (5)
O3B	0.0641 (8)	0.0866 (9)	0.0729 (9)	−0.0045 (7)	−0.0138 (7)	−0.0458 (8)
O4A	0.0758 (9)	0.0461 (7)	0.0658 (8)	−0.0045 (6)	−0.0038 (6)	−0.0182 (6)
S1B	0.0526 (2)	0.0518 (2)	0.0476 (2)	−0.01414 (18)	−0.00393 (18)	−0.00294 (18)
S1A	0.0614 (3)	0.0439 (2)	0.0653 (3)	0.00323 (18)	−0.0282 (2)	−0.01838 (19)
O4B	0.0605 (18)	0.116 (7)	0.089 (5)	−0.015 (3)	0.001 (2)	−0.064 (5)
O4B'	0.075 (7)	0.105 (13)	0.078 (8)	0.010 (8)	−0.011 (6)	−0.058 (9)

Geometric parameters (Å, º)

N1A—C4A	1.369 (2)	C8A—C9A	1.382 (2)
N1A—C3A	1.371 (2)	C8A—C13A	1.388 (2)
N1A—H1A	0.8600	C8B—C9B	1.376 (2)
O1B—C4B	1.207 (2)	C8B—C13B	1.376 (2)
O2A—C2A	1.226 (2)	C13B—C12B	1.377 (2)
C5A—C4A	1.488 (2)	C13B—H13B	0.9300
C5A—H5A1	0.9600	C9A—C10A	1.380 (3)
C5A—H5A2	0.9600	C9A—H9A	0.9300
C5A—H5A3	0.9600	C12B—C11B	1.359 (2)
C5B—C4B	1.496 (3)	C12B—H12B	0.9300
C5B—H5B1	0.9600	C10A—C11A	1.367 (3)
C5B—H5B2	0.9600	C10A—H10A	0.9300
C5B—H5B3	0.9600	C11B—C10B	1.355 (3)
C4B—N1B	1.365 (2)	C11B—O3B	1.406 (2)
C4A—O1A	1.207 (2)	C11A—C12A	1.371 (3)
C3B—N2B	1.277 (2)	C11A—O3A	1.400 (2)
C3B—N1B	1.377 (2)	C10B—C9B	1.383 (3)
C3B—S1B	1.7420 (15)	C10B—H10B	0.9300
C3A—N2A	1.2821 (19)	C12A—C13A	1.373 (3)
C3A—S1A	1.7353 (16)	C12A—H12A	0.9300
C2B—O2B	1.228 (2)	C13A—H13A	0.9300
C2B—N3B	1.352 (2)	C9B—H9B	0.9300
C2B—C1B	1.495 (2)	C14B—O4B	1.196 (7)
C2A—N3A	1.352 (2)	C14B—O4B'	1.218 (14)
C2A—C1A	1.494 (3)	C14B—O3B	1.341 (2)
C1A—H1A1	0.9600	C14B—C15B	1.491 (3)
C1A—H1A2	0.9600	C14A—O4A	1.195 (2)
C1A—H1A3	0.9600	C14A—O3A	1.355 (2)
C1B—H1B1	0.9600	C14A—C15A	1.484 (2)
C1B—H1B2	0.9600	C15B—C16B	1.508 (3)
C1B—H1B3	0.9600	C15B—H15A	0.9700
C6A—N3A	1.485 (2)	C15B—H15B	0.9700
C6A—C8A	1.515 (2)	C15A—C16A	1.511 (3)
C6A—C7A	1.523 (3)	C15A—H15C	0.9700
C6A—S1A	1.8520 (16)	C15A—H15D	0.9700
C6B—N3B	1.4887 (19)	C16A—H16A	0.9600
C6B—C8B	1.523 (2)	C16A—H16B	0.9600
C6B—C7B	1.526 (2)	C16A—H16C	0.9600
C6B—S1B	1.8531 (16)	C16B—H16D	0.9600
C7B—H7B1	0.9600	C16B—H16E	0.9600
C7B—H7B2	0.9600	C16B—H16F	0.9600
C7B—H7B3	0.9600	N1B—H1B	0.8600
C7A—H7A1	0.9600	N2B—N3B	1.3993 (17)
C7A—H7A2	0.9600	N2A—N3A	1.3973 (19)
C7A—H7A3	0.9600
C4A—N1A—C3A	124.42 (14)	C8B—C13B—H13B	119.3
C4A—N1A—H1A	117.8	C12B—C13B—H13B	119.3
C3A—N1A—H1A	117.8	C10A—C9A—C8A	121.04 (17)
C4A—C5A—H5A1	109.5	C10A—C9A—H9A	119.5
C4A—C5A—H5A2	109.5	C8A—C9A—H9A	119.5
H5A1—C5A—H5A2	109.5	C11B—C12B—C13B	119.62 (16)
C4A—C5A—H5A3	109.5	C11B—C12B—H12B	120.2
H5A1—C5A—H5A3	109.5	C13B—C12B—H12B	120.2
H5A2—C5A—H5A3	109.5	C11A—C10A—C9A	119.44 (17)
C4B—C5B—H5B1	109.5	C11A—C10A—H10A	120.3
C4B—C5B—H5B2	109.5	C9A—C10A—H10A	120.3
H5B1—C5B—H5B2	109.5	C10B—C11B—C12B	120.48 (16)
C4B—C5B—H5B3	109.5	C10B—C11B—O3B	118.06 (16)
H5B1—C5B—H5B3	109.5	C12B—C11B—O3B	121.31 (16)
H5B2—C5B—H5B3	109.5	C10A—C11A—C12A	121.05 (17)
O1B—C4B—N1B	121.23 (17)	C10A—C11A—O3A	118.62 (16)
O1B—C4B—C5B	123.57 (18)	C12A—C11A—O3A	120.17 (17)
N1B—C4B—C5B	115.18 (17)	C11B—C10B—C9B	119.73 (17)
O1A—C4A—N1A	120.96 (16)	C11B—C10B—H10B	120.1
O1A—C4A—C5A	123.29 (17)	C9B—C10B—H10B	120.1
N1A—C4A—C5A	115.74 (16)	C11A—C12A—C13A	118.98 (18)
N2B—C3B—N1B	119.51 (14)	C11A—C12A—H12A	120.5
N2B—C3B—S1B	118.75 (12)	C13A—C12A—H12A	120.5
N1B—C3B—S1B	121.73 (12)	C12A—C13A—C8A	121.63 (16)
N2A—C3A—N1A	120.77 (14)	C12A—C13A—H13A	119.2
N2A—C3A—S1A	118.74 (12)	C8A—C13A—H13A	119.2
N1A—C3A—S1A	120.46 (11)	C8B—C9B—C10B	121.19 (17)
O2B—C2B—N3B	120.27 (15)	C8B—C9B—H9B	119.4
O2B—C2B—C1B	122.29 (16)	C10B—C9B—H9B	119.4
N3B—C2B—C1B	117.44 (15)	O4B—C14B—O3B	120.9 (4)
O2A—C2A—N3A	120.37 (16)	O4B'—C14B—O3B	121.3 (8)
O2A—C2A—C1A	122.52 (16)	O4B—C14B—C15B	126.8 (4)
N3A—C2A—C1A	117.10 (17)	O4B'—C14B—C15B	122.2 (11)
C2A—C1A—H1A1	109.5	O3B—C14B—C15B	111.26 (17)
C2A—C1A—H1A2	109.5	O4A—C14A—O3A	122.58 (16)
H1A1—C1A—H1A2	109.5	O4A—C14A—C15A	126.69 (18)
C2A—C1A—H1A3	109.5	O3A—C14A—C15A	110.72 (15)
H1A1—C1A—H1A3	109.5	C14B—C15B—C16B	113.05 (19)
H1A2—C1A—H1A3	109.5	C14B—C15B—H15A	109.0
C2B—C1B—H1B1	109.5	C16B—C15B—H15A	109.0
C2B—C1B—H1B2	109.5	C14B—C15B—H15B	109.0
H1B1—C1B—H1B2	109.5	C16B—C15B—H15B	109.0
C2B—C1B—H1B3	109.5	H15A—C15B—H15B	107.8
H1B1—C1B—H1B3	109.5	C14A—C15A—C16A	111.95 (17)
H1B2—C1B—H1B3	109.5	C14A—C15A—H15C	109.2
N3A—C6A—C8A	112.33 (13)	C16A—C15A—H15C	109.2
N3A—C6A—C7A	110.08 (14)	C14A—C15A—H15D	109.2
C8A—C6A—C7A	115.48 (14)	C16A—C15A—H15D	109.2
N3A—C6A—S1A	102.03 (10)	H15C—C15A—H15D	107.9
C8A—C6A—S1A	106.50 (11)	C15A—C16A—H16A	109.5
C7A—C6A—S1A	109.47 (12)	C15A—C16A—H16B	109.5
N3B—C6B—C8B	110.60 (12)	H16A—C16A—H16B	109.5
N3B—C6B—C7B	112.08 (13)	C15A—C16A—H16C	109.5
C8B—C6B—C7B	114.21 (13)	H16A—C16A—H16C	109.5
N3B—C6B—S1B	102.21 (10)	H16B—C16A—H16C	109.5
C8B—C6B—S1B	109.71 (11)	C15B—C16B—H16D	109.5
C7B—C6B—S1B	107.27 (12)	C15B—C16B—H16E	109.5
C6B—C7B—H7B1	109.5	H16D—C16B—H16E	109.5
C6B—C7B—H7B2	109.5	C15B—C16B—H16F	109.5
H7B1—C7B—H7B2	109.5	H16D—C16B—H16F	109.5
C6B—C7B—H7B3	109.5	H16E—C16B—H16F	109.5
H7B1—C7B—H7B3	109.5	C4B—N1B—C3B	124.47 (15)
H7B2—C7B—H7B3	109.5	C4B—N1B—H1B	117.8
C6A—C7A—H7A1	109.5	C3B—N1B—H1B	117.8
C6A—C7A—H7A2	109.5	C3B—N2B—N3B	110.39 (12)
H7A1—C7A—H7A2	109.5	C3A—N2A—N3A	110.07 (13)
C6A—C7A—H7A3	109.5	C2A—N3A—N2A	120.02 (14)
H7A1—C7A—H7A3	109.5	C2A—N3A—C6A	122.34 (14)
H7A2—C7A—H7A3	109.5	N2A—N3A—C6A	117.49 (12)
C9A—C8A—C13A	117.81 (16)	C2B—N3B—N2B	119.44 (13)
C9A—C8A—C6A	121.21 (15)	C2B—N3B—C6B	122.35 (13)
C13A—C8A—C6A	120.81 (15)	N2B—N3B—C6B	117.53 (12)
C9B—C8B—C13B	117.51 (15)	C14A—O3A—C11A	118.09 (13)
C9B—C8B—C6B	121.12 (14)	C14B—O3B—C11B	118.32 (15)
C13B—C8B—C6B	121.36 (13)	C3B—S1B—C6B	89.96 (7)
C8B—C13B—C12B	121.48 (15)	C3A—S1A—C6A	89.90 (7)
C3A—N1A—C4A—O1A	1.8 (3)	S1B—C3B—N2B—N3B	−0.89 (18)
C3A—N1A—C4A—C5A	−177.04 (17)	N1A—C3A—N2A—N3A	−177.85 (14)
C4A—N1A—C3A—N2A	176.96 (17)	S1A—C3A—N2A—N3A	0.39 (19)
C4A—N1A—C3A—S1A	−1.2 (2)	O2A—C2A—N3A—N2A	172.94 (16)
N3A—C6A—C8A—C9A	156.77 (15)	C1A—C2A—N3A—N2A	−8.5 (3)
C7A—C6A—C8A—C9A	29.4 (2)	O2A—C2A—N3A—C6A	−2.5 (3)
S1A—C6A—C8A—C9A	−92.34 (16)	C1A—C2A—N3A—C6A	176.07 (18)
N3A—C6A—C8A—C13A	−28.1 (2)	C3A—N2A—N3A—C2A	173.99 (16)
C7A—C6A—C8A—C13A	−155.50 (16)	C3A—N2A—N3A—C6A	−10.4 (2)
S1A—C6A—C8A—C13A	82.75 (16)	C8A—C6A—N3A—C2A	−56.7 (2)
N3B—C6B—C8B—C9B	160.12 (18)	C7A—C6A—N3A—C2A	73.5 (2)
C7B—C6B—C8B—C9B	32.6 (2)	S1A—C6A—N3A—C2A	−170.36 (14)
S1B—C6B—C8B—C9B	−87.87 (19)	C8A—C6A—N3A—N2A	127.76 (14)
N3B—C6B—C8B—C13B	−21.2 (2)	C7A—C6A—N3A—N2A	−102.04 (16)
C7B—C6B—C8B—C13B	−148.76 (16)	S1A—C6A—N3A—N2A	14.10 (17)
S1B—C6B—C8B—C13B	90.79 (16)	O2B—C2B—N3B—N2B	−176.98 (14)
C9B—C8B—C13B—C12B	0.2 (3)	C1B—C2B—N3B—N2B	2.7 (2)
C6B—C8B—C13B—C12B	−178.50 (16)	O2B—C2B—N3B—C6B	−6.7 (2)
C13A—C8A—C9A—C10A	1.0 (3)	C1B—C2B—N3B—C6B	172.99 (15)
C6A—C8A—C9A—C10A	176.22 (16)	C3B—N2B—N3B—C2B	179.54 (14)
C8B—C13B—C12B—C11B	−0.1 (3)	C3B—N2B—N3B—C6B	8.79 (19)
C8A—C9A—C10A—C11A	0.9 (3)	C8B—C6B—N3B—C2B	−65.22 (18)
C13B—C12B—C11B—C10B	−0.3 (3)	C7B—C6B—N3B—C2B	63.48 (19)
C13B—C12B—C11B—O3B	−175.85 (17)	S1B—C6B—N3B—C2B	178.04 (12)
C9A—C10A—C11A—C12A	−1.6 (3)	C8B—C6B—N3B—N2B	105.25 (15)
C9A—C10A—C11A—O3A	173.75 (16)	C7B—C6B—N3B—N2B	−126.05 (15)
C12B—C11B—C10B—C9B	0.5 (4)	S1B—C6B—N3B—N2B	−11.50 (15)
O3B—C11B—C10B—C9B	176.2 (2)	O4A—C14A—O3A—C11A	−6.9 (2)
C10A—C11A—C12A—C13A	0.5 (3)	C15A—C14A—O3A—C11A	174.20 (15)
O3A—C11A—C12A—C13A	−174.87 (16)	C10A—C11A—O3A—C14A	119.16 (18)
C11A—C12A—C13A—C8A	1.5 (3)	C12A—C11A—O3A—C14A	−65.4 (2)
C9A—C8A—C13A—C12A	−2.2 (3)	O4B—C14B—O3B—C11B	−9.4 (16)
C6A—C8A—C13A—C12A	−177.47 (16)	O4B'—C14B—O3B—C11B	27 (3)
C13B—C8B—C9B—C10B	0.0 (3)	C15B—C14B—O3B—C11B	−178.40 (16)
C6B—C8B—C9B—C10B	178.7 (2)	C10B—C11B—O3B—C14B	110.6 (2)
C11B—C10B—C9B—C8B	−0.4 (4)	C12B—C11B—O3B—C14B	−73.7 (2)
O4B—C14B—C15B—C16B	9.9 (17)	N2B—C3B—S1B—C6B	−5.09 (13)
O4B'—C14B—C15B—C16B	−27 (3)	N1B—C3B—S1B—C6B	173.34 (14)
O3B—C14B—C15B—C16B	178.04 (18)	N3B—C6B—S1B—C3B	8.44 (10)
O4A—C14A—C15A—C16A	−6.8 (3)	C8B—C6B—S1B—C3B	−108.95 (11)
O3A—C14A—C15A—C16A	172.10 (18)	C7B—C6B—S1B—C3B	126.48 (12)
O1B—C4B—N1B—C3B	−2.5 (3)	N2A—C3A—S1A—C6A	6.85 (15)
C5B—C4B—N1B—C3B	175.98 (18)	N1A—C3A—S1A—C6A	−174.91 (14)
N2B—C3B—N1B—C4B	−167.01 (16)	N3A—C6A—S1A—C3A	−10.64 (11)
S1B—C3B—N1B—C4B	14.6 (2)	C8A—C6A—S1A—C3A	−128.55 (11)
N1B—C3B—N2B—N3B	−179.36 (13)	C7A—C6A—S1A—C3A	105.95 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O2B^i	0.86	1.99	2.8469 (19)	174
N1B—H1B···O2A^ii	0.86	2.04	2.860 (2)	160
C9B—H9B···O3A^iii	0.93	2.60	3.426 (2)	148

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

4-(5-Acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl cinnamate chloroform hemisolvate (IV)

Crystal data

C22H21N3O4S·0.5CHCl3	Z = 4
Mr = 483.16	F(000) = 1004
Triclinic, P1	Dx = 1.350 Mg m^−3
a = 10.7427 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.0828 (2) Å	Cell parameters from 8335 reflections
c = 20.8969 (3) Å	θ = 1.8–26.9°
α = 93.186 (1)°	µ = 0.34 mm^−1
β = 103.945 (4)°	T = 293 K
γ = 98.489 (2)°	Block, colourless
V = 2377.39 (7) Å^3	0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	6495 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.027
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 25.0°, θmin = 1.9°
Tmin = 0.741, Tmax = 0.856	h = −12→12
31719 measured reflections	k = −13→13
8335 independent reflections	l = −24→24

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.195	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.1202P)^2 + 0.801P] where P = (Fo^2 + 2Fc^2)/3
8335 reflections	(Δ/σ)max = 0.001
583 parameters	Δρmax = 0.54 e Å^−3
0 restraints	Δρmin = −0.60 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
C1A	0.7194 (4)	0.1544 (3)	0.06419 (17)	0.0762 (10)
H1A1	0.679416	0.205916	0.032712	0.114*
H1A2	0.656947	0.117324	0.086277	0.114*
H1A3	0.749989	0.091555	0.041580	0.114*
C1B	0.6139 (3)	0.7996 (3)	0.05275 (15)	0.0639 (8)
H1B1	0.695480	0.854537	0.064442	0.096*
H1B2	0.544321	0.845480	0.051555	0.096*
H1B3	0.602589	0.757019	0.009951	0.096*
C2A	0.8309 (3)	0.2293 (3)	0.11376 (14)	0.0533 (7)
C2B	0.6126 (3)	0.7094 (2)	0.10287 (13)	0.0484 (6)
C3A	0.9511 (2)	0.0017 (2)	0.20325 (12)	0.0428 (5)
C3B	0.3223 (2)	0.5173 (2)	0.03235 (12)	0.0427 (5)
C4A	1.0210 (3)	−0.1768 (3)	0.25439 (14)	0.0513 (6)
C4B	0.1169 (3)	0.3955 (3)	−0.02802 (15)	0.0583 (7)
C5A	0.9753 (3)	−0.3054 (3)	0.26544 (17)	0.0680 (8)
H5A1	1.045685	−0.351101	0.269622	0.102*
H5A2	0.905121	−0.341904	0.228557	0.102*
H5A3	0.945710	−0.306228	0.305263	0.102*
C5B	0.0036 (3)	0.3916 (4)	−0.08641 (18)	0.0799 (10)
H5B1	−0.051581	0.313263	−0.092202	0.120*
H5B2	0.034438	0.403920	−0.125414	0.120*
H5B3	−0.044694	0.455046	−0.079113	0.120*
C6A	1.0106 (2)	0.2332 (2)	0.21533 (13)	0.0465 (6)
C6B	0.4970 (2)	0.5235 (2)	0.13959 (12)	0.0432 (5)
C7A	1.1137 (3)	0.3185 (3)	0.19223 (17)	0.0632 (8)
H7A1	1.128809	0.280281	0.153057	0.095*
H7A2	1.193202	0.334094	0.226558	0.095*
H7A3	1.083562	0.394438	0.182604	0.095*
C7B	0.6069 (3)	0.4474 (3)	0.14865 (15)	0.0574 (7)
H7B1	0.611552	0.413704	0.106132	0.086*
H7B2	0.590135	0.382120	0.175304	0.086*
H7B3	0.687998	0.498827	0.170196	0.086*
C8A	0.9573 (2)	0.2918 (2)	0.26755 (13)	0.0439 (6)
C8B	0.4791 (2)	0.5838 (2)	0.20332 (12)	0.0430 (5)
C9A	0.8302 (3)	0.2560 (3)	0.27116 (15)	0.0579 (7)
H9A	0.774920	0.197301	0.239339	0.069*
C9B	0.5678 (3)	0.5896 (3)	0.26339 (14)	0.0604 (7)
H9B	0.642341	0.554829	0.266019	0.072*
C10A	0.7844 (3)	0.3056 (3)	0.32095 (16)	0.0636 (8)
H10A	0.698835	0.280633	0.322681	0.076*
C10B	0.5487 (3)	0.6453 (3)	0.31927 (15)	0.0672 (8)
H10B	0.609121	0.646886	0.359678	0.081*
C11A	0.8654 (3)	0.3919 (3)	0.36804 (14)	0.0549 (7)
C11B	0.4411 (3)	0.6985 (3)	0.31586 (14)	0.0543 (7)
C12A	0.9920 (3)	0.4299 (3)	0.36570 (15)	0.0574 (7)
H12A	1.046685	0.488670	0.397663	0.069*
C12B	0.3529 (3)	0.6951 (4)	0.25795 (16)	0.0733 (9)
H12B	0.279542	0.731560	0.255771	0.088*
C13A	1.0363 (3)	0.3802 (3)	0.31574 (14)	0.0530 (7)
H13A	1.121732	0.406325	0.314039	0.064*
C13B	0.3712 (3)	0.6372 (4)	0.20168 (15)	0.0702 (9)
H13B	0.309114	0.634359	0.161743	0.084*
C14A	0.8162 (3)	0.5525 (3)	0.43336 (15)	0.0570 (7)
C14B	0.3303 (3)	0.7229 (3)	0.39933 (14)	0.0551 (7)
C15A	0.7524 (3)	0.5734 (3)	0.48581 (14)	0.0606 (7)
H15A	0.722788	0.507454	0.506914	0.073*
C15B	0.3246 (3)	0.8066 (3)	0.45431 (14)	0.0590 (7)
H15B	0.395847	0.867181	0.473069	0.071*
C16A	0.7357 (3)	0.6851 (3)	0.50409 (14)	0.0582 (7)
H16A	0.767123	0.747609	0.481341	0.070*
C16B	0.2218 (3)	0.7990 (3)	0.47811 (14)	0.0563 (7)
H16B	0.154112	0.735313	0.458827	0.068*
C17A	0.6744 (3)	0.7222 (3)	0.55536 (14)	0.0571 (7)
C17B	0.2007 (3)	0.8783 (3)	0.53116 (13)	0.0527 (6)
C18A	0.6129 (4)	0.6396 (3)	0.5895 (2)	0.0805 (10)
H18A	0.607888	0.556028	0.579260	0.097*
C18B	0.0791 (3)	0.8648 (4)	0.54331 (18)	0.0796 (10)
H18B	0.012376	0.805620	0.517842	0.096*
C19A	0.5588 (4)	0.6798 (4)	0.6385 (2)	0.0973 (13)
H19A	0.516647	0.623096	0.660692	0.117*
C19B	0.0559 (4)	0.9382 (5)	0.5928 (2)	0.1002 (14)
H19B	−0.026287	0.927828	0.600861	0.120*
C20A	0.5667 (4)	0.8028 (4)	0.6549 (2)	0.0883 (12)
H20A	0.530013	0.829440	0.687996	0.106*
C20B	0.1510 (5)	1.0252 (4)	0.6299 (2)	0.0951 (13)
H20B	0.133699	1.075734	0.662592	0.114*
C21A	0.6284 (3)	0.8853 (4)	0.62237 (18)	0.0754 (10)
H21A	0.634720	0.968781	0.633653	0.090*
C21B	0.2717 (5)	1.0388 (4)	0.61940 (19)	0.0928 (13)
H21B	0.337669	1.098062	0.645371	0.111*
C22A	0.6817 (3)	0.8462 (3)	0.57277 (16)	0.0656 (8)
H22A	0.723142	0.903687	0.550683	0.079*
C22B	0.2968 (3)	0.9659 (3)	0.57086 (16)	0.0704 (9)
H22B	0.380255	0.975483	0.564433	0.085*
C24	1.3645 (7)	0.9979 (5)	0.1756 (3)	0.1254 (18)
H24	1.320200	0.999896	0.211398	0.150*
N1A	0.9043 (2)	0.1694 (2)	0.15926 (10)	0.0479 (5)
N1B	0.5106 (2)	0.61660 (19)	0.09130 (10)	0.0433 (5)
N2A	0.9315 (2)	−0.1208 (2)	0.21358 (11)	0.0470 (5)
H2A	0.858413	−0.164752	0.193076	0.056*
N2B	0.2116 (2)	0.4957 (2)	−0.01916 (11)	0.0502 (5)
H2B	0.201657	0.548981	−0.047555	0.060*
N3A	0.8666 (2)	0.04364 (19)	0.16030 (11)	0.0469 (5)
N3B	0.4087 (2)	0.61029 (19)	0.03472 (10)	0.0445 (5)
O1A	0.8567 (2)	0.34125 (19)	0.11497 (11)	0.0623 (5)
O1B	0.70071 (19)	0.7159 (2)	0.15333 (10)	0.0637 (5)
O2A	1.1291 (2)	−0.1226 (2)	0.28060 (13)	0.0768 (7)
O2B	0.1249 (3)	0.3165 (2)	0.00948 (13)	0.0913 (8)
O3A	0.8151 (2)	0.4318 (2)	0.42002 (11)	0.0691 (6)
O3B	0.4300 (2)	0.7646 (2)	0.37297 (10)	0.0688 (6)
O4A	0.8612 (3)	0.6288 (2)	0.40394 (13)	0.0848 (8)
O4B	0.2575 (2)	0.6284 (2)	0.37835 (12)	0.0732 (6)
Cl1	1.5222 (2)	0.9672 (2)	0.20900 (13)	0.1808 (8)
Cl2	1.2776 (3)	0.8889 (2)	0.11689 (11)	0.2206 (13)
Cl3	1.3765 (3)	1.14052 (19)	0.14707 (17)	0.2181 (12)
S1A	1.08765 (6)	0.10243 (6)	0.24908 (4)	0.0508 (2)
S1B	0.34553 (7)	0.42085 (6)	0.09567 (3)	0.0545 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.082 (2)	0.065 (2)	0.067 (2)	0.0200 (17)	−0.0145 (17)	0.0092 (16)
C1B	0.0673 (18)	0.0550 (17)	0.0610 (17)	−0.0091 (14)	0.0098 (14)	0.0149 (14)
C2A	0.0551 (15)	0.0531 (17)	0.0535 (15)	0.0188 (13)	0.0101 (13)	0.0093 (12)
C2B	0.0463 (14)	0.0460 (14)	0.0510 (15)	0.0035 (11)	0.0110 (12)	0.0059 (11)
C3A	0.0395 (12)	0.0463 (14)	0.0437 (13)	0.0122 (10)	0.0097 (10)	0.0046 (11)
C3B	0.0470 (13)	0.0409 (13)	0.0413 (13)	0.0067 (11)	0.0136 (10)	0.0038 (10)
C4A	0.0485 (15)	0.0518 (15)	0.0544 (15)	0.0179 (12)	0.0084 (12)	0.0055 (12)
C4B	0.0587 (16)	0.0536 (17)	0.0563 (16)	−0.0040 (13)	0.0114 (13)	0.0007 (14)
C5A	0.0688 (19)	0.0624 (19)	0.071 (2)	0.0157 (15)	0.0074 (16)	0.0210 (15)
C5B	0.068 (2)	0.076 (2)	0.075 (2)	−0.0125 (17)	−0.0051 (17)	−0.0012 (18)
C6A	0.0375 (12)	0.0462 (14)	0.0553 (15)	0.0080 (10)	0.0090 (11)	0.0094 (11)
C6B	0.0468 (13)	0.0433 (13)	0.0422 (13)	0.0083 (10)	0.0143 (10)	0.0106 (10)
C7A	0.0517 (16)	0.0670 (19)	0.0725 (19)	0.0017 (14)	0.0215 (14)	0.0158 (15)
C7B	0.0640 (17)	0.0566 (17)	0.0588 (16)	0.0224 (14)	0.0210 (14)	0.0104 (13)
C8A	0.0391 (12)	0.0391 (13)	0.0522 (14)	0.0072 (10)	0.0072 (11)	0.0106 (11)
C8B	0.0404 (12)	0.0481 (14)	0.0416 (13)	0.0088 (10)	0.0104 (10)	0.0097 (10)
C9A	0.0432 (14)	0.0574 (17)	0.0686 (18)	−0.0024 (12)	0.0151 (13)	−0.0080 (14)
C9B	0.0535 (16)	0.079 (2)	0.0504 (16)	0.0248 (14)	0.0077 (13)	0.0047 (14)
C10A	0.0484 (15)	0.0632 (19)	0.080 (2)	0.0017 (13)	0.0239 (15)	−0.0034 (16)
C10B	0.0640 (18)	0.089 (2)	0.0446 (15)	0.0199 (16)	0.0038 (13)	−0.0036 (15)
C11A	0.0644 (17)	0.0493 (15)	0.0547 (16)	0.0140 (13)	0.0188 (13)	0.0063 (12)
C11B	0.0523 (15)	0.0601 (17)	0.0498 (15)	−0.0003 (13)	0.0195 (12)	−0.0050 (13)
C12A	0.0552 (16)	0.0505 (16)	0.0596 (17)	0.0053 (13)	0.0051 (13)	−0.0037 (13)
C12B	0.0629 (18)	0.103 (3)	0.0615 (18)	0.0410 (18)	0.0159 (15)	−0.0015 (18)
C13A	0.0397 (13)	0.0475 (15)	0.0659 (17)	0.0024 (11)	0.0054 (12)	0.0017 (13)
C13B	0.0597 (18)	0.106 (3)	0.0482 (16)	0.0386 (18)	0.0066 (14)	0.0016 (16)
C14A	0.0629 (17)	0.0595 (18)	0.0515 (15)	0.0194 (14)	0.0134 (13)	0.0090 (14)
C14B	0.0583 (16)	0.0581 (17)	0.0510 (15)	0.0077 (14)	0.0195 (13)	0.0038 (13)
C15A	0.0626 (17)	0.070 (2)	0.0518 (16)	0.0162 (15)	0.0148 (14)	0.0086 (14)
C15B	0.0604 (17)	0.0621 (18)	0.0525 (16)	0.0006 (14)	0.0185 (13)	−0.0034 (13)
C16A	0.0579 (16)	0.0639 (18)	0.0537 (16)	0.0156 (14)	0.0118 (13)	0.0082 (13)
C16B	0.0610 (17)	0.0563 (17)	0.0521 (15)	0.0044 (13)	0.0188 (13)	0.0036 (13)
C17A	0.0501 (15)	0.0641 (18)	0.0551 (16)	0.0129 (13)	0.0084 (12)	0.0005 (14)
C17B	0.0589 (16)	0.0563 (16)	0.0472 (14)	0.0114 (13)	0.0196 (12)	0.0082 (12)
C18A	0.087 (2)	0.065 (2)	0.100 (3)	0.0131 (18)	0.046 (2)	−0.0006 (19)
C18B	0.0610 (19)	0.103 (3)	0.076 (2)	0.0076 (18)	0.0262 (17)	−0.005 (2)
C19A	0.104 (3)	0.091 (3)	0.115 (3)	0.009 (2)	0.066 (3)	0.008 (2)
C19B	0.079 (3)	0.144 (4)	0.093 (3)	0.034 (3)	0.046 (2)	0.001 (3)
C20A	0.078 (2)	0.098 (3)	0.093 (3)	0.008 (2)	0.038 (2)	−0.020 (2)
C20B	0.126 (4)	0.099 (3)	0.074 (2)	0.031 (3)	0.047 (3)	−0.009 (2)
C21A	0.0651 (19)	0.074 (2)	0.080 (2)	0.0074 (17)	0.0121 (17)	−0.0206 (18)
C21B	0.116 (3)	0.087 (3)	0.069 (2)	−0.013 (2)	0.035 (2)	−0.017 (2)
C22A	0.0594 (17)	0.069 (2)	0.0665 (19)	0.0123 (15)	0.0124 (15)	0.0028 (15)
C22B	0.0693 (19)	0.078 (2)	0.0634 (19)	−0.0020 (16)	0.0272 (16)	−0.0027 (16)
C24	0.168 (5)	0.093 (3)	0.119 (4)	0.023 (3)	0.043 (4)	0.006 (3)
N1A	0.0458 (11)	0.0486 (12)	0.0466 (12)	0.0108 (9)	0.0037 (9)	0.0088 (9)
N1B	0.0444 (11)	0.0436 (11)	0.0404 (11)	0.0034 (9)	0.0091 (9)	0.0086 (9)
N2A	0.0415 (11)	0.0471 (12)	0.0500 (12)	0.0090 (9)	0.0055 (9)	0.0059 (9)
N2B	0.0505 (12)	0.0498 (13)	0.0457 (12)	0.0005 (10)	0.0067 (10)	0.0097 (10)
N3A	0.0456 (11)	0.0440 (12)	0.0479 (12)	0.0093 (9)	0.0045 (9)	0.0055 (9)
N3B	0.0440 (11)	0.0464 (12)	0.0399 (11)	0.0032 (9)	0.0065 (9)	0.0059 (9)
O1A	0.0632 (12)	0.0530 (12)	0.0688 (13)	0.0158 (9)	0.0061 (10)	0.0190 (10)
O1B	0.0515 (11)	0.0662 (13)	0.0604 (12)	−0.0058 (9)	−0.0027 (9)	0.0112 (10)
O2A	0.0540 (12)	0.0581 (13)	0.1058 (18)	0.0173 (10)	−0.0092 (12)	0.0100 (12)
O2B	0.0909 (18)	0.0728 (16)	0.0852 (17)	−0.0283 (13)	−0.0044 (14)	0.0229 (14)
O3A	0.0904 (16)	0.0576 (13)	0.0693 (13)	0.0136 (11)	0.0388 (12)	0.0051 (10)
O3B	0.0651 (12)	0.0771 (15)	0.0625 (12)	−0.0080 (11)	0.0302 (10)	−0.0173 (11)
O4A	0.121 (2)	0.0660 (15)	0.0900 (17)	0.0323 (14)	0.0583 (16)	0.0181 (13)
O4B	0.0861 (15)	0.0571 (13)	0.0781 (15)	−0.0089 (12)	0.0397 (12)	−0.0078 (11)
Cl1	0.1491 (16)	0.1571 (16)	0.220 (2)	0.0242 (13)	0.0127 (15)	0.0345 (15)
Cl2	0.292 (3)	0.1581 (18)	0.1448 (16)	0.0026 (19)	−0.0530 (18)	0.0216 (13)
Cl3	0.261 (3)	0.1176 (13)	0.342 (3)	0.0661 (16)	0.164 (3)	0.1005 (18)
S1A	0.0372 (3)	0.0504 (4)	0.0610 (4)	0.0115 (3)	0.0027 (3)	0.0053 (3)
S1B	0.0620 (4)	0.0483 (4)	0.0473 (4)	−0.0053 (3)	0.0097 (3)	0.0128 (3)

Geometric parameters (Å, º)

C1A—C2A	1.487 (4)	C10B—H10B	0.9300
C1A—H1A1	0.9600	C11A—C12A	1.376 (4)
C1A—H1A2	0.9600	C11A—O3A	1.403 (3)
C1A—H1A3	0.9600	C11B—C12B	1.340 (4)
C1B—C2B	1.489 (4)	C11B—O3B	1.404 (3)
C1B—H1B1	0.9600	C12A—C13A	1.369 (4)
C1B—H1B2	0.9600	C12A—H12A	0.9300
C1B—H1B3	0.9600	C12B—C13B	1.377 (4)
C2A—O1A	1.228 (3)	C12B—H12B	0.9300
C2A—N1A	1.353 (3)	C13A—H13A	0.9300
C2B—O1B	1.226 (3)	C13B—H13B	0.9300
C2B—N1B	1.352 (3)	C14A—O4A	1.187 (4)
C3A—N3A	1.275 (3)	C14A—O3A	1.350 (4)
C3A—N2A	1.379 (3)	C14A—C15A	1.451 (4)
C3A—S1A	1.742 (3)	C14B—O4B	1.202 (4)
C3B—N3B	1.271 (3)	C14B—O3B	1.353 (4)
C3B—N2B	1.379 (3)	C14B—C15B	1.455 (4)
C3B—S1B	1.741 (3)	C15A—C16A	1.325 (4)
C4A—O2A	1.209 (3)	C15A—H15A	0.9300
C4A—N2A	1.370 (3)	C15B—C16B	1.310 (4)
C4A—C5A	1.486 (4)	C15B—H15B	0.9300
C4B—O2B	1.206 (4)	C16A—C17A	1.457 (4)
C4B—N2B	1.362 (4)	C16A—H16A	0.9300
C4B—C5B	1.495 (4)	C16B—C17B	1.457 (4)
C5A—H5A1	0.9600	C16B—H16B	0.9300
C5A—H5A2	0.9600	C17A—C18A	1.379 (5)
C5A—H5A3	0.9600	C17A—C22A	1.388 (4)
C5B—H5B1	0.9600	C17B—C22B	1.378 (4)
C5B—H5B2	0.9600	C17B—C18B	1.379 (4)
C5B—H5B3	0.9600	C18A—C19A	1.378 (5)
C6A—N1A	1.484 (3)	C18A—H18A	0.9300
C6A—C8A	1.508 (4)	C18B—C19B	1.373 (5)
C6A—C7A	1.533 (4)	C18B—H18B	0.9300
C6A—S1A	1.863 (3)	C19A—C20A	1.372 (6)
C6B—N1B	1.499 (3)	C19A—H19A	0.9300
C6B—C8B	1.523 (3)	C19B—C20B	1.348 (7)
C6B—C7B	1.531 (4)	C19B—H19B	0.9300
C6B—S1B	1.845 (3)	C20A—C21A	1.358 (6)
C7A—H7A1	0.9600	C20A—H20A	0.9300
C7A—H7A2	0.9600	C20B—C21B	1.355 (6)
C7A—H7A3	0.9600	C20B—H20B	0.9300
C7B—H7B1	0.9600	C21A—C22A	1.378 (5)
C7B—H7B2	0.9600	C21A—H21A	0.9300
C7B—H7B3	0.9600	C21B—C22B	1.364 (5)
C8A—C9A	1.386 (4)	C21B—H21B	0.9300
C8A—C13A	1.388 (4)	C22A—H22A	0.9300
C8B—C13B	1.371 (4)	C22B—H22B	0.9300
C8B—C9B	1.373 (4)	C24—Cl2	1.669 (6)
C9A—C10A	1.375 (4)	C24—Cl3	1.718 (6)
C9A—H9A	0.9300	C24—Cl1	1.761 (7)
C9B—C10B	1.363 (4)	C24—H24	0.9800
C9B—H9B	0.9300	N1A—N3A	1.396 (3)
C10A—C11A	1.370 (4)	N1B—N3B	1.395 (3)
C10A—H10A	0.9300	N2A—H2A	0.8600
C10B—C11B	1.362 (4)	N2B—H2B	0.8600
C2A—C1A—H1A1	109.5	C13A—C12A—C11A	119.2 (3)
C2A—C1A—H1A2	109.5	C13A—C12A—H12A	120.4
H1A1—C1A—H1A2	109.5	C11A—C12A—H12A	120.4
C2A—C1A—H1A3	109.5	C11B—C12B—C13B	119.7 (3)
H1A1—C1A—H1A3	109.5	C11B—C12B—H12B	120.1
H1A2—C1A—H1A3	109.5	C13B—C12B—H12B	120.1
C2B—C1B—H1B1	109.5	C12A—C13A—C8A	121.8 (3)
C2B—C1B—H1B2	109.5	C12A—C13A—H13A	119.1
H1B1—C1B—H1B2	109.5	C8A—C13A—H13A	119.1
C2B—C1B—H1B3	109.5	C8B—C13B—C12B	121.4 (3)
H1B1—C1B—H1B3	109.5	C8B—C13B—H13B	119.3
H1B2—C1B—H1B3	109.5	C12B—C13B—H13B	119.3
O1A—C2A—N1A	120.1 (3)	O4A—C14A—O3A	122.9 (3)
O1A—C2A—C1A	122.7 (2)	O4A—C14A—C15A	126.1 (3)
N1A—C2A—C1A	117.2 (3)	O3A—C14A—C15A	111.0 (3)
O1B—C2B—N1B	119.5 (2)	O4B—C14B—O3B	122.5 (3)
O1B—C2B—C1B	122.4 (2)	O4B—C14B—C15B	126.1 (3)
N1B—C2B—C1B	118.1 (2)	O3B—C14B—C15B	111.4 (3)
N3A—C3A—N2A	119.8 (2)	C16A—C15A—C14A	121.0 (3)
N3A—C3A—S1A	118.7 (2)	C16A—C15A—H15A	119.5
N2A—C3A—S1A	121.56 (18)	C14A—C15A—H15A	119.5
N3B—C3B—N2B	119.9 (2)	C16B—C15B—C14B	121.8 (3)
N3B—C3B—S1B	118.86 (19)	C16B—C15B—H15B	119.1
N2B—C3B—S1B	121.26 (19)	C14B—C15B—H15B	119.1
O2A—C4A—N2A	121.2 (3)	C15A—C16A—C17A	128.1 (3)
O2A—C4A—C5A	122.9 (3)	C15A—C16A—H16A	115.9
N2A—C4A—C5A	115.9 (2)	C17A—C16A—H16A	115.9
O2B—C4B—N2B	121.5 (3)	C15B—C16B—C17B	127.8 (3)
O2B—C4B—C5B	123.0 (3)	C15B—C16B—H16B	116.1
N2B—C4B—C5B	115.5 (3)	C17B—C16B—H16B	116.1
C4A—C5A—H5A1	109.5	C18A—C17A—C22A	118.0 (3)
C4A—C5A—H5A2	109.5	C18A—C17A—C16A	123.0 (3)
H5A1—C5A—H5A2	109.5	C22A—C17A—C16A	119.0 (3)
C4A—C5A—H5A3	109.5	C22B—C17B—C18B	117.7 (3)
H5A1—C5A—H5A3	109.5	C22B—C17B—C16B	123.5 (3)
H5A2—C5A—H5A3	109.5	C18B—C17B—C16B	118.9 (3)
C4B—C5B—H5B1	109.5	C19A—C18A—C17A	120.6 (4)
C4B—C5B—H5B2	109.5	C19A—C18A—H18A	119.7
H5B1—C5B—H5B2	109.5	C17A—C18A—H18A	119.7
C4B—C5B—H5B3	109.5	C19B—C18B—C17B	120.3 (4)
H5B1—C5B—H5B3	109.5	C19B—C18B—H18B	119.8
H5B2—C5B—H5B3	109.5	C17B—C18B—H18B	119.8
N1A—C6A—C8A	111.2 (2)	C20A—C19A—C18A	120.5 (4)
N1A—C6A—C7A	112.5 (2)	C20A—C19A—H19A	119.7
C8A—C6A—C7A	114.9 (2)	C18A—C19A—H19A	119.7
N1A—C6A—S1A	101.33 (16)	C20B—C19B—C18B	120.7 (4)
C8A—C6A—S1A	108.81 (17)	C20B—C19B—H19B	119.6
C7A—C6A—S1A	107.09 (18)	C18B—C19B—H19B	119.6
N1B—C6B—C8B	110.5 (2)	C21A—C20A—C19A	119.6 (4)
N1B—C6B—C7B	111.1 (2)	C21A—C20A—H20A	120.2
C8B—C6B—C7B	115.2 (2)	C19A—C20A—H20A	120.2
N1B—C6B—S1B	102.28 (15)	C19B—C20B—C21B	119.9 (4)
C8B—C6B—S1B	109.63 (16)	C19B—C20B—H20B	120.1
C7B—C6B—S1B	107.21 (19)	C21B—C20B—H20B	120.1
C6A—C7A—H7A1	109.5	C20A—C21A—C22A	120.4 (3)
C6A—C7A—H7A2	109.5	C20A—C21A—H21A	119.8
H7A1—C7A—H7A2	109.5	C22A—C21A—H21A	119.8
C6A—C7A—H7A3	109.5	C20B—C21B—C22B	120.1 (4)
H7A1—C7A—H7A3	109.5	C20B—C21B—H21B	119.9
H7A2—C7A—H7A3	109.5	C22B—C21B—H21B	119.9
C6B—C7B—H7B1	109.5	C21A—C22A—C17A	120.9 (3)
C6B—C7B—H7B2	109.5	C21A—C22A—H22A	119.6
H7B1—C7B—H7B2	109.5	C17A—C22A—H22A	119.6
C6B—C7B—H7B3	109.5	C21B—C22B—C17B	121.2 (3)
H7B1—C7B—H7B3	109.5	C21B—C22B—H22B	119.4
H7B2—C7B—H7B3	109.5	C17B—C22B—H22B	119.4
C9A—C8A—C13A	117.6 (3)	Cl2—C24—Cl3	112.3 (4)
C9A—C8A—C6A	121.6 (2)	Cl2—C24—Cl1	111.7 (3)
C13A—C8A—C6A	120.7 (2)	Cl3—C24—Cl1	108.8 (4)
C13B—C8B—C9B	117.3 (2)	Cl2—C24—H24	107.9
C13B—C8B—C6B	119.6 (2)	Cl3—C24—H24	107.9
C9B—C8B—C6B	123.0 (2)	Cl1—C24—H24	107.9
C10A—C9A—C8A	121.1 (3)	C2A—N1A—N3A	118.9 (2)
C10A—C9A—H9A	119.4	C2A—N1A—C6A	123.1 (2)
C8A—C9A—H9A	119.4	N3A—N1A—C6A	117.22 (19)
C10B—C9B—C8B	121.3 (3)	C2B—N1B—N3B	119.7 (2)
C10B—C9B—H9B	119.4	C2B—N1B—C6B	122.5 (2)
C8B—C9B—H9B	119.4	N3B—N1B—C6B	117.59 (19)
C11A—C10A—C9A	119.7 (3)	C4A—N2A—C3A	124.2 (2)
C11A—C10A—H10A	120.1	C4A—N2A—H2A	117.9
C9A—C10A—H10A	120.1	C3A—N2A—H2A	117.9
C11B—C10B—C9B	119.9 (3)	C4B—N2B—C3B	124.3 (2)
C11B—C10B—H10B	120.0	C4B—N2B—H2B	117.8
C9B—C10B—H10B	120.0	C3B—N2B—H2B	117.8
C10A—C11A—C12A	120.6 (3)	C3A—N3A—N1A	110.1 (2)
C10A—C11A—O3A	116.6 (3)	C3B—N3B—N1B	110.6 (2)
C12A—C11A—O3A	122.7 (3)	C14A—O3A—C11A	119.8 (2)
C12B—C11B—C10B	120.3 (3)	C14B—O3B—C11B	117.8 (2)
C12B—C11B—O3B	120.9 (3)	C3A—S1A—C6A	89.27 (11)
C10B—C11B—O3B	118.6 (3)	C3B—S1B—C6B	90.27 (11)
N1A—C6A—C8A—C9A	18.9 (3)	C18B—C17B—C22B—C21B	−1.6 (5)
C7A—C6A—C8A—C9A	148.1 (3)	C16B—C17B—C22B—C21B	179.2 (3)
S1A—C6A—C8A—C9A	−91.9 (3)	O1A—C2A—N1A—N3A	174.7 (2)
N1A—C6A—C8A—C13A	−164.1 (2)	C1A—C2A—N1A—N3A	−4.5 (4)
C7A—C6A—C8A—C13A	−34.9 (3)	O1A—C2A—N1A—C6A	5.1 (4)
S1A—C6A—C8A—C13A	85.1 (3)	C1A—C2A—N1A—C6A	−174.1 (3)
N1B—C6B—C8B—C13B	63.4 (3)	C8A—C6A—N1A—C2A	73.6 (3)
C7B—C6B—C8B—C13B	−169.6 (3)	C7A—C6A—N1A—C2A	−56.8 (3)
S1B—C6B—C8B—C13B	−48.6 (3)	S1A—C6A—N1A—C2A	−170.9 (2)
N1B—C6B—C8B—C9B	−115.5 (3)	C8A—C6A—N1A—N3A	−96.1 (2)
C7B—C6B—C8B—C9B	11.5 (4)	C7A—C6A—N1A—N3A	133.4 (2)
S1B—C6B—C8B—C9B	132.5 (3)	S1A—C6A—N1A—N3A	19.4 (2)
C13A—C8A—C9A—C10A	−0.4 (4)	O1B—C2B—N1B—N3B	178.5 (2)
C6A—C8A—C9A—C10A	176.7 (3)	C1B—C2B—N1B—N3B	−2.1 (4)
C13B—C8B—C9B—C10B	0.6 (5)	O1B—C2B—N1B—C6B	3.1 (4)
C6B—C8B—C9B—C10B	179.5 (3)	C1B—C2B—N1B—C6B	−177.6 (2)
C8A—C9A—C10A—C11A	−0.1 (5)	C8B—C6B—N1B—C2B	65.2 (3)
C8B—C9B—C10B—C11B	−1.2 (5)	C7B—C6B—N1B—C2B	−64.0 (3)
C9A—C10A—C11A—C12A	0.4 (5)	S1B—C6B—N1B—C2B	−178.2 (2)
C9A—C10A—C11A—O3A	−175.4 (3)	C8B—C6B—N1B—N3B	−110.4 (2)
C9B—C10B—C11B—C12B	0.9 (5)	C7B—C6B—N1B—N3B	120.4 (2)
C9B—C10B—C11B—O3B	−174.3 (3)	S1B—C6B—N1B—N3B	6.3 (2)
C10A—C11A—C12A—C13A	−0.1 (5)	O2A—C4A—N2A—C3A	−5.8 (4)
O3A—C11A—C12A—C13A	175.4 (3)	C5A—C4A—N2A—C3A	172.6 (3)
C10B—C11B—C12B—C13B	0.1 (6)	N3A—C3A—N2A—C4A	174.3 (2)
O3B—C11B—C12B—C13B	175.2 (3)	S1A—C3A—N2A—C4A	−7.2 (4)
C11A—C12A—C13A—C8A	−0.4 (4)	O2B—C4B—N2B—C3B	−0.7 (5)
C9A—C8A—C13A—C12A	0.7 (4)	C5B—C4B—N2B—C3B	178.8 (3)
C6A—C8A—C13A—C12A	−176.5 (3)	N3B—C3B—N2B—C4B	176.4 (3)
C9B—C8B—C13B—C12B	0.4 (5)	S1B—C3B—N2B—C4B	−4.9 (4)
C6B—C8B—C13B—C12B	−178.5 (3)	N2A—C3A—N3A—N1A	178.5 (2)
C11B—C12B—C13B—C8B	−0.7 (6)	S1A—C3A—N3A—N1A	0.0 (3)
O4A—C14A—C15A—C16A	2.2 (5)	C2A—N1A—N3A—C3A	175.8 (2)
O3A—C14A—C15A—C16A	−176.0 (3)	C6A—N1A—N3A—C3A	−14.0 (3)
O4B—C14B—C15B—C16B	−14.4 (5)	N2B—C3B—N3B—N1B	178.6 (2)
O3B—C14B—C15B—C16B	165.3 (3)	S1B—C3B—N3B—N1B	−0.2 (3)
C14A—C15A—C16A—C17A	−180.0 (3)	C2B—N1B—N3B—C3B	179.9 (2)
C14B—C15B—C16B—C17B	−177.9 (3)	C6B—N1B—N3B—C3B	−4.4 (3)
C15A—C16A—C17A—C18A	−5.9 (5)	O4A—C14A—O3A—C11A	−2.0 (5)
C15A—C16A—C17A—C22A	171.7 (3)	C15A—C14A—O3A—C11A	176.3 (2)
C15B—C16B—C17B—C22B	−9.2 (5)	C10A—C11A—O3A—C14A	−125.4 (3)
C15B—C16B—C17B—C18B	171.7 (3)	C12A—C11A—O3A—C14A	58.9 (4)
C22A—C17A—C18A—C19A	1.0 (6)	O4B—C14B—O3B—C11B	5.0 (5)
C16A—C17A—C18A—C19A	178.6 (4)	C15B—C14B—O3B—C11B	−174.7 (3)
C22B—C17B—C18B—C19B	0.9 (6)	C12B—C11B—O3B—C14B	68.0 (4)
C16B—C17B—C18B—C19B	−179.8 (4)	C10B—C11B—O3B—C14B	−116.7 (3)
C17A—C18A—C19A—C20A	−0.9 (7)	N3A—C3A—S1A—C6A	9.8 (2)
C17B—C18B—C19B—C20B	0.6 (7)	N2A—C3A—S1A—C6A	−168.6 (2)
C18A—C19A—C20A—C21A	0.0 (7)	N1A—C6A—S1A—C3A	−14.77 (17)
C18B—C19B—C20B—C21B	−1.5 (8)	C8A—C6A—S1A—C3A	102.52 (18)
C19A—C20A—C21A—C22A	0.7 (6)	C7A—C6A—S1A—C3A	−132.8 (2)
C19B—C20B—C21B—C22B	0.9 (7)	N3B—C3B—S1B—C6B	3.4 (2)
C20A—C21A—C22A—C17A	−0.5 (5)	N2B—C3B—S1B—C6B	−175.3 (2)
C18A—C17A—C22A—C21A	−0.4 (5)	N1B—C6B—S1B—C3B	−4.89 (16)
C16A—C17A—C22A—C21A	−178.1 (3)	C8B—C6B—S1B—C3B	112.41 (18)
C20B—C21B—C22B—C17B	0.7 (7)	C7B—C6B—S1B—C3B	−121.86 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A···O1B^i	0.86	1.96	2.815 (3)	172
N2B—H2B···O1A^ii	0.86	1.96	2.810 (3)	169
C5A—H5A2···O1B^i	0.96	2.56	3.344 (4)	139
C5A—H5A3···O4A^i	0.96	2.54	3.477 (4)	164
C12B—H12B···O2A^iii	0.93	2.56	3.459 (4)	161

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