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Pyrroloquinoline quinone (PQQ) is a water-soluble quinone compound first identified as a cofactor of alcohol- and glucose-dehydrogenases (ADH and GDH) in bacteria. For example, in the process of ADH reaction, alcohol is oxidized to the corresponding aldehyde, and inversely PQQ is reduced to pyrroloquinoline quinol (PQQH2). PQQ and PQQH2 molecules play an important role as a cofactor in ADH and GDH reactions. However, crystal structure analysis has not been performed for PQQ and PQQH2. In the present study, the synthesis of PQQH2 powder crystals was performed under air, by utilizing vitamin C as a reducing agent. By reacting a trihydrate of disodium salt of PQQ (PQQNa2·3H2O) with excess vitamin C in H2O at 293 and 343 K, yellowish brown and black powder crystals of PQQH2 having different properties were obtained in high yield, respectively. The former was PQQH2 trihydrate (PQQH2·3H2O) and the latter was PQQH2 anhydrate (PQQH2). Furthermore, sodium-free red PQQ powder crystal (a monohydrate of PQQ, PQQ·H2O) was prepared by the reaction of PQQNa2·3H2O with HCl in H2O. Single crystals of PQQH2 and PQQ were prepared from Me2SO/CH3CN mixed solvent, and we have succeeded in the crystal structure analyses of PQQH2 and PQQ for the first time.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520617002281/xk5034sup1.cif
Contains datablocks I, II, global

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617002281/xk5034Isup2.fcf
Contains datablock I

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617002281/xk5034IIsup3.fcf
Contains datablock II

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520617002281/xk5034sup4.pdf
Supporting figures and tables

CCDC references: 1487730; 1487731

Computing details top

For both compounds, data collection: CrystalClear (Rigaku Inc., 2008); cell refinement: CrystalClear (Rigaku Inc., 2008); data reduction: CrystalClear (Rigaku Inc., 2008); program(s) used to solve structure: SIR2011 (Burla, et al., 2012); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2016); molecular graphics: CrystalStructure 4.2.4 (Rigaku, 2016); software used to prepare material for publication: CrystalStructure 4.2.4 (Rigaku, 2016).

(I) top
Crystal data top
2(C7H4NO4)·2(C2H6OS)·C2H3NDx = 1.536 Mg m3
Mr = 529.53Mo Kα radiation, λ = 0.71075 Å
Orthorhombic, PnmaCell parameters from 6974 reflections
a = 14.563 (5) Åθ = 2.2–31.2°
b = 6.748 (2) ŵ = 0.30 mm1
c = 23.299 (9) ÅT = 100 K
V = 2289.6 (14) Å3Needle, orange
Z = 40.24 × 0.03 × 0.02 mm
F(000) = 1104
Data collection top
Rigaku Saturn724
diffractometer
2990 independent reflections
Radiation source: Varimax 50 kV 24 mA Rotating anode2846 reflections with I > 2σ(I)
Detector resolution: 7.111 pixels mm-1Rint = 0.051
ω scansθmax = 28.0°, θmin = 2.2°
Absorption correction: multi-scan
REQAB (Rigaku, 1998)
h = 1919
Tmin = 0.912, Tmax = 0.994k = 88
38156 measured reflectionsl = 3030
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: mixed
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.053P)2 + 3.2P]
where P = (Fo2 + 2Fc2)/3
2990 reflections(Δ/σ)max = 0.001
267 parametersΔρmax = 0.48 e Å3
236 restraintsΔρmin = 0.36 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.95984 (15)0.2500000.25191 (9)0.0413 (6)
O21.11256 (15)0.2500000.25846 (9)0.0310 (5)
H2O1.099 (3)0.2500000.2922 (18)0.037*
O31.23564 (13)0.2500000.02383 (9)0.0251 (5)
H3O1.257 (2)0.2500000.0141 (16)0.030*
O41.14103 (14)0.2500000.07778 (9)0.0290 (5)
H4O1.110 (3)0.2500000.1046 (17)0.035*
O50.74435 (14)0.2500000.15150 (9)0.0316 (5)
O60.88455 (14)0.2500000.18742 (8)0.0246 (4)
H6O0.945 (3)0.2500000.1763 (16)0.030*
O70.79196 (14)0.2500000.11706 (8)0.0301 (5)
O80.68979 (15)0.2500000.04710 (9)0.0430 (7)
H8O0.654 (3)0.2500000.076 (2)0.052*
N10.97079 (16)0.2500000.13227 (9)0.0195 (5)
H1N0.913 (2)0.2500000.1430 (15)0.023*
C21.04677 (19)0.2500000.16660 (11)0.0207 (5)
C31.12426 (18)0.2500000.13281 (11)0.0197 (5)
H31.1861860.2500000.1456260.024*
C3A1.09347 (17)0.2500000.07514 (11)0.0178 (5)
C41.14201 (18)0.2500000.02226 (12)0.0199 (5)
C51.09317 (18)0.2500000.02786 (11)0.0188 (5)
C5A0.99512 (18)0.2500000.02736 (11)0.0165 (5)
N60.95695 (15)0.2500000.08022 (9)0.0171 (4)
C70.86636 (18)0.2500000.08423 (11)0.0182 (5)
C80.80810 (18)0.2500000.03693 (11)0.0190 (5)
H80.7434380.2500000.0423150.023*
C90.84439 (18)0.2500000.01811 (11)0.0169 (5)
C9A0.94206 (18)0.2500000.02498 (11)0.0169 (5)
C1A0.99642 (18)0.2500000.07598 (11)0.0169 (5)
C101.0344 (2)0.2500000.22905 (12)0.0241 (6)
C110.82666 (19)0.2500000.14344 (11)0.0216 (6)
C120.77507 (18)0.2500000.06616 (12)0.0218 (6)
S1S1.13174 (5)0.2500000.23528 (3)0.0292 (2)
C1S1.20922 (16)0.4481 (4)0.22216 (10)0.0391 (6)
H1SA1.2316360.4403470.1825670.047*
H1SB1.1775510.5746820.2279690.047*
H1SC1.2612290.4386610.2487150.047*
O1S1.06649 (16)0.2500000.18464 (10)0.0490 (8)
S2S0.46451 (11)0.3252 (3)0.11996 (11)0.0298 (4)0.3586 (15)
C2SA0.4619 (5)0.3930 (14)0.0459 (3)0.0472 (19)0.3586 (15)
H2SA0.4830500.5300480.0415750.071*0.3586 (15)
H2SB0.3988990.3816540.0313690.071*0.3586 (15)
H2SC0.5021470.3045190.0240050.071*0.3586 (15)
C2SB0.3990 (12)0.105 (2)0.1158 (7)0.040 (3)0.3586 (15)
H2SD0.4360740.0000020.0983750.060*0.3586 (15)
H2SE0.3442870.1286740.0922470.060*0.3586 (15)
H2SF0.3802150.0648180.1544680.060*0.3586 (15)
O2S0.56169 (16)0.230 (2)0.12930 (11)0.0312 (14)0.3586 (15)
S3S0.4719 (2)0.2500000.08417 (17)0.0343 (9)0.244 (2)
C3S0.3985 (19)0.058 (3)0.1078 (12)0.035 (4)0.244 (2)
H3SA0.4077240.0595480.0837780.052*0.244 (2)
H3SB0.3345060.1016260.1048590.052*0.244 (2)
H3SC0.4126740.0255480.1478160.052*0.244 (2)
O3S0.56169 (16)0.230 (2)0.12930 (11)0.0312 (14)0.1221 (12)
S4S0.4585 (15)0.2500000.120 (2)0.034 (3)0.039 (3)
C4S0.415 (4)0.439 (9)0.072 (3)0.038 (6)0.039 (3)
H4SA0.4351740.5698240.0860140.057*0.039 (3)
H4SB0.3481150.4340260.0715260.057*0.039 (3)
H4SC0.4393640.4169350.0335720.057*0.039 (3)
O4S0.56169 (16)0.230 (2)0.12930 (11)0.0312 (14)0.0193 (14)
N1S1.3585 (2)0.2500000.07550 (13)0.0440 (8)
C5S1.3906 (2)0.2500000.11983 (14)0.0360 (8)
C6S1.4333 (2)0.2500000.17659 (14)0.0401 (9)
H6SA1.4322240.1154400.1923970.060*0.5
H6SB1.4970040.2953570.1733430.060*0.5
H6SC1.3992850.3392030.2020850.060*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0236 (11)0.083 (2)0.0178 (10)0.0000.0041 (8)0.000
O20.0229 (10)0.0516 (14)0.0184 (10)0.0000.0074 (8)0.000
O30.0125 (9)0.0402 (12)0.0227 (10)0.0000.0007 (7)0.000
O40.0178 (10)0.0528 (15)0.0163 (9)0.0000.0032 (7)0.000
O50.0195 (10)0.0566 (15)0.0188 (10)0.0000.0025 (8)0.000
O60.0222 (10)0.0373 (12)0.0143 (9)0.0000.0000 (7)0.000
O70.0202 (10)0.0563 (15)0.0138 (9)0.0000.0008 (7)0.000
O80.0172 (10)0.095 (2)0.0171 (10)0.0000.0027 (8)0.000
N10.0159 (11)0.0295 (13)0.0131 (10)0.0000.0021 (8)0.000
C20.0208 (13)0.0263 (14)0.0151 (12)0.0000.0052 (10)0.000
C30.0181 (12)0.0214 (13)0.0197 (12)0.0000.0066 (10)0.000
C3A0.0160 (12)0.0188 (13)0.0185 (12)0.0000.0024 (9)0.000
C40.0153 (12)0.0219 (13)0.0223 (13)0.0000.0016 (10)0.000
C50.0155 (12)0.0238 (14)0.0170 (12)0.0000.0017 (9)0.000
C5A0.0170 (12)0.0170 (12)0.0157 (11)0.0000.0007 (9)0.000
N60.0184 (10)0.0195 (11)0.0134 (10)0.0000.0012 (8)0.000
C70.0181 (12)0.0209 (13)0.0157 (12)0.0000.0023 (9)0.000
C80.0161 (12)0.0224 (13)0.0184 (12)0.0000.0024 (9)0.000
C90.0172 (12)0.0187 (12)0.0148 (11)0.0000.0000 (9)0.000
C9A0.0175 (12)0.0177 (12)0.0156 (12)0.0000.0015 (9)0.000
C1A0.0189 (12)0.0168 (12)0.0151 (11)0.0000.0027 (9)0.000
C100.0234 (13)0.0315 (15)0.0174 (12)0.0000.0044 (10)0.000
C110.0195 (12)0.0296 (15)0.0157 (12)0.0000.0006 (10)0.000
C120.0163 (12)0.0295 (15)0.0197 (12)0.0000.0002 (10)0.000
S1S0.0175 (3)0.0544 (5)0.0159 (3)0.0000.0012 (2)0.000
C1S0.0306 (11)0.0483 (15)0.0382 (12)0.0033 (11)0.0020 (9)0.0138 (11)
O1S0.0205 (11)0.108 (2)0.0187 (11)0.0000.0036 (9)0.000
S2S0.0205 (7)0.0445 (9)0.0243 (8)0.0046 (7)0.0048 (6)0.0045 (11)
C2SA0.040 (3)0.073 (5)0.029 (3)0.019 (3)0.016 (3)0.026 (3)
C2SB0.017 (4)0.068 (7)0.036 (5)0.010 (5)0.012 (3)0.003 (5)
O2S0.0175 (10)0.051 (4)0.0252 (10)0.001 (2)0.0026 (8)0.000 (2)
S3S0.0211 (14)0.052 (2)0.0296 (19)0.0000.0010 (12)0.000
C3S0.026 (6)0.039 (7)0.040 (8)0.010 (5)0.013 (5)0.004 (5)
O3S0.0175 (10)0.051 (4)0.0252 (10)0.001 (2)0.0026 (8)0.000 (2)
S4S0.026 (4)0.049 (5)0.028 (5)0.0000.005 (4)0.000
C4S0.032 (9)0.051 (10)0.032 (9)0.005 (9)0.005 (9)0.003 (9)
O4S0.0175 (10)0.051 (4)0.0252 (10)0.001 (2)0.0026 (8)0.000 (2)
N1S0.0285 (14)0.075 (2)0.0284 (14)0.0000.0039 (12)0.000
C5S0.0232 (14)0.059 (2)0.0261 (15)0.0000.0015 (12)0.000
C6S0.0293 (16)0.067 (3)0.0243 (15)0.0000.0032 (13)0.000
Geometric parameters (Å, º) top
O1—C101.209 (4)S1S—C1Si1.776 (3)
O2—C101.329 (3)C1S—H1SA0.9800
O2—H2O0.81 (4)C1S—H1SB0.9800
O3—C41.364 (3)C1S—H1SC0.9800
O3—H3O0.94 (4)S2S—O2S1.569 (6)
O4—C51.356 (3)S2S—C2SB1.768 (11)
O4—H4O0.77 (4)S2S—C2SA1.786 (6)
O5—C111.213 (3)C2SA—H2SA0.9800
O6—C111.327 (3)C2SA—H2SB0.9800
O6—H6O0.91 (4)C2SA—H2SC0.9800
O7—C121.211 (3)C2SB—H2SD0.9800
O8—C121.319 (3)C2SB—H2SE0.9800
O8—H8O0.86 (5)C2SB—H2SF0.9800
N1—C1A1.364 (3)S3S—O3S1.684 (4)
N1—C21.365 (3)S3S—O3Si1.684 (4)
N1—H1N0.88 (4)S3S—C3S1.767 (16)
C2—C31.376 (4)S3S—C3Si1.767 (16)
C2—C101.466 (4)C3S—H3SA0.9800
C3—C3A1.417 (4)C3S—H3SB0.9800
C3—H30.9500C3S—H3SC0.9800
C3A—C1A1.413 (4)O3S—O3Si0.27 (3)
C3A—C41.420 (4)S4S—O4S1.525 (19)
C4—C51.367 (4)S4S—C4Si1.81 (2)
C5—C5A1.428 (4)S4S—C4S1.81 (2)
C5A—N61.351 (3)C4S—H4SA0.9800
C5A—C9A1.444 (3)C4S—H4SB0.9800
N6—C71.322 (3)C4S—H4SC0.9800
C7—C81.391 (4)N1S—C5S1.133 (4)
C7—C111.496 (4)C5S—C6S1.462 (4)
C8—C91.387 (3)C6S—H6SA0.9800
C8—H80.9500C6S—H6SB0.9800
C9—C9A1.431 (4)C6S—H6SC0.9800
C9—C121.508 (4)C6S—H6SAi0.980 (11)
C9A—C1A1.428 (3)C6S—H6SBi0.98 (2)
S1S—O1S1.515 (2)C6S—H6SCi0.98 (3)
S1S—C1S1.776 (3)
C10—O2—H2O107 (3)S1S—C1S—H1SC109.5
C4—O3—H3O108 (2)H1SA—C1S—H1SC109.5
C5—O4—H4O113 (3)H1SB—C1S—H1SC109.5
C11—O6—H6O113 (2)O2S—S2S—C2SB98.7 (8)
C12—O8—H8O108 (3)O2S—S2S—C2SA105.0 (3)
C1A—N1—C2110.0 (2)C2SB—S2S—C2SA98.6 (6)
C1A—N1—H1N122 (2)S2S—C2SA—H2SA109.5
C2—N1—H1N128 (2)S2S—C2SA—H2SB109.5
N1—C2—C3109.2 (2)H2SA—C2SA—H2SB109.5
N1—C2—C10118.8 (2)S2S—C2SA—H2SC109.5
C3—C2—C10132.0 (2)H2SA—C2SA—H2SC109.5
C2—C3—C3A106.4 (2)H2SB—C2SA—H2SC109.5
C2—C3—H3126.8S2S—C2SB—H2SD109.5
C3A—C3—H3126.8S2S—C2SB—H2SE109.5
C1A—C3A—C3107.7 (2)H2SD—C2SB—H2SE109.5
C1A—C3A—C4120.6 (2)S2S—C2SB—H2SF109.5
C3—C3A—C4131.7 (2)H2SD—C2SB—H2SF109.5
O3—C4—C5122.9 (2)H2SE—C2SB—H2SF109.5
O3—C4—C3A118.3 (2)O3S—S3S—C3S102.6 (11)
C5—C4—C3A118.8 (2)O3Si—S3S—C3S109.5 (11)
O4—C5—C4117.7 (2)S3S—C3S—H3SA109.5
O4—C5—C5A121.4 (2)S3S—C3S—H3SB109.5
C4—C5—C5A120.9 (2)H3SA—C3S—H3SB109.5
N6—C5A—C5113.8 (2)S3S—C3S—H3SC109.5
N6—C5A—C9A123.3 (2)H3SA—C3S—H3SC109.5
C5—C5A—C9A122.8 (2)H3SB—C3S—H3SC109.5
C7—N6—C5A118.4 (2)O3Si—O3S—S3S85.5 (5)
N6—C7—C8123.5 (2)O4S—S4S—C4S119 (3)
N6—C7—C11116.8 (2)C4Si—S4S—C4S90 (5)
C8—C7—C11119.7 (2)S4S—C4S—H4SA109.5
C9—C8—C7120.0 (2)S4S—C4S—H4SB109.5
C9—C8—H8120.0H4SA—C4S—H4SB109.5
C7—C8—H8120.0S4S—C4S—H4SC109.5
C8—C9—C9A118.8 (2)H4SA—C4S—H4SC109.5
C8—C9—C12115.6 (2)H4SB—C4S—H4SC109.5
C9A—C9—C12125.6 (2)N1S—C5S—C6S179.1 (4)
C1A—C9A—C9130.1 (2)C5S—C6S—H6SA109.5
C1A—C9A—C5A114.0 (2)C5S—C6S—H6SB109.5
C9—C9A—C5A115.9 (2)H6SA—C6S—H6SB109.5
N1—C1A—C3A106.7 (2)C5S—C6S—H6SC109.5
N1—C1A—C9A130.4 (2)H6SA—C6S—H6SC109.5
C3A—C1A—C9A122.9 (2)H6SB—C6S—H6SC109.5
O1—C10—O2122.8 (3)C5S—C6S—H6SAi109.5 (2)
O1—C10—C2123.2 (3)H6SA—C6S—H6SAi135.8
O2—C10—C2114.0 (2)H6SB—C6S—H6SAi75.8
O5—C11—O6120.5 (2)H6SC—C6S—H6SAi36.4
O5—C11—C7121.6 (2)C5S—C6S—H6SBi109.5 (4)
O6—C11—C7117.8 (2)H6SA—C6S—H6SBi75.8
O7—C12—O8121.4 (3)H6SB—C6S—H6SBi36.4
O7—C12—C9126.2 (2)H6SC—C6S—H6SBi135.8
O8—C12—C9112.4 (2)H6SAi—C6S—H6SBi109.5
O1S—S1S—C1S105.34 (10)C5S—C6S—H6SCi109.5 (7)
O1S—S1S—C1Si105.34 (10)H6SA—C6S—H6SCi36.4
C1S—S1S—C1Si97.67 (17)H6SB—C6S—H6SCi135.8
S1S—C1S—H1SA109.5H6SC—C6S—H6SCi75.8
S1S—C1S—H1SB109.5H6SAi—C6S—H6SCi109.5
H1SA—C1S—H1SB109.5H6SBi—C6S—H6SCi109.5
C1A—N1—C2—C30.000 (1)C12—C9—C9A—C5A180.0
C1A—N1—C2—C10180.000 (1)N6—C5A—C9A—C1A180.0
N1—C2—C3—C3A0.000 (1)C5—C5A—C9A—C1A0.0
C10—C2—C3—C3A180.000 (1)N6—C5A—C9A—C90.0
C2—C3—C3A—C1A0.000 (1)C5—C5A—C9A—C9180.0
C2—C3—C3A—C4180.000 (1)C2—N1—C1A—C3A0.000 (1)
C1A—C3A—C4—O3180.0C2—N1—C1A—C9A180.000 (1)
C3—C3A—C4—O30.000 (1)C3—C3A—C1A—N10.000 (1)
C1A—C3A—C4—C50.0C4—C3A—C1A—N1180.000 (1)
C3—C3A—C4—C5180.000 (1)C3—C3A—C1A—C9A180.000 (1)
O3—C4—C5—O40.0C4—C3A—C1A—C9A0.000 (1)
C3A—C4—C5—O4180.0C9—C9A—C1A—N10.000 (1)
O3—C4—C5—C5A180.0C5A—C9A—C1A—N1180.0
C3A—C4—C5—C5A0.0C9—C9A—C1A—C3A180.0
O4—C5—C5A—N60.0C5A—C9A—C1A—C3A0.0
C4—C5—C5A—N6180.0N1—C2—C10—O10.000 (1)
O4—C5—C5A—C9A180.0C3—C2—C10—O1180.000 (1)
C4—C5—C5A—C9A0.0N1—C2—C10—O2180.000 (1)
C5—C5A—N6—C7180.0C3—C2—C10—O20.000 (1)
C9A—C5A—N6—C70.0N6—C7—C11—O5180.000 (1)
C5A—N6—C7—C80.000 (1)C8—C7—C11—O50.000 (1)
C5A—N6—C7—C11180.000 (1)N6—C7—C11—O60.000 (1)
N6—C7—C8—C90.0C8—C7—C11—O6180.000 (1)
C11—C7—C8—C9180.000 (1)C8—C9—C12—O7180.0
C7—C8—C9—C9A0.0C9A—C9—C12—O70.0
C7—C8—C9—C12180.0C8—C9—C12—O80.0
C8—C9—C9A—C1A180.0C9A—C9—C12—O8180.0
C12—C9—C9A—C1A0.0C3S—S3S—O3S—O3Si140.5 (8)
C8—C9—C9A—C5A0.0C3Si—S3S—O3S—O3Si41.2 (9)
Symmetry code: (i) x, y+1/2, z.
(II) top
Crystal data top
C14H6N2O8·3(C2H6OS)Dx = 1.532 Mg m3
Mr = 564.59Mo Kα radiation, λ = 0.71075 Å
Orthorhombic, P212121Cell parameters from 7223 reflections
a = 6.901 (5) Åθ = 2.2–31.3°
b = 12.371 (8) ŵ = 0.37 mm1
c = 28.674 (18) ÅT = 100 K
V = 2448 (3) Å3Block, orange
Z = 40.05 × 0.05 × 0.02 mm
F(000) = 1176
Data collection top
Rigaku Saturn724
diffractometer
5885 independent reflections
Radiation source: Varimax 50 kV 24 mA Rotating anode4968 reflections with I > 2σ(I)
Detector resolution: 7.111 pixels mm-1Rint = 0.077
ω scansθmax = 28.0°, θmin = 2.2°
Absorption correction: multi-scan
REQAB (Rigaku, 1998)
h = 99
Tmin = 0.910, Tmax = 0.993k = 1616
41911 measured reflectionsl = 3737
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.070H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.185 w = 1/[σ2(Fo2) + (0.0801P)2 + 4.9734P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
5885 reflectionsΔρmax = 1.43 e Å3
337 parametersΔρmin = 0.78 e Å3
0 restraintsAbsolute structure: Flack x determined using 1648 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.12 (3)
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.9440 (7)0.8466 (4)0.05934 (17)0.0218 (10)
H1N0.914 (10)0.906 (6)0.039 (2)0.026*
C20.9653 (9)0.8499 (4)0.10737 (18)0.0218 (11)
C30.9869 (9)0.7459 (4)0.12347 (17)0.0206 (10)
H31.0043710.7240120.1549500.025*
C3A0.9777 (8)0.6775 (4)0.08356 (17)0.0190 (10)
C40.9825 (9)0.5605 (4)0.08101 (17)0.0203 (10)
C50.9453 (8)0.5134 (4)0.03123 (19)0.0220 (11)
C5A0.9399 (8)0.5897 (4)0.01008 (18)0.0194 (10)
N60.9387 (7)0.5391 (4)0.05150 (16)0.0218 (9)
C70.9494 (8)0.6010 (4)0.08993 (18)0.0204 (11)
C80.9599 (8)0.7140 (4)0.08793 (19)0.0215 (11)
H80.9728140.7546510.1158630.026*
C90.9516 (8)0.7667 (4)0.04513 (19)0.0210 (11)
C9A0.9441 (8)0.7031 (4)0.00378 (19)0.0194 (10)
C1A0.9501 (8)0.7430 (4)0.04392 (19)0.0209 (11)
C100.9588 (9)0.9563 (5)0.1305 (2)0.0276 (13)
C110.9544 (9)0.5438 (5)0.13669 (19)0.0264 (13)
C120.9484 (8)0.8898 (4)0.04803 (19)0.0216 (11)
O10.9249 (9)1.0384 (4)0.10878 (17)0.0431 (13)
O20.9909 (8)0.9506 (3)0.17610 (13)0.0281 (8)
H2O0.9903251.0131110.1875000.042*
O31.0089 (8)0.4989 (3)0.11352 (13)0.0288 (9)
O40.9196 (7)0.4173 (3)0.02732 (15)0.0274 (9)
O50.9234 (8)0.4468 (3)0.14038 (15)0.0332 (11)
O60.9905 (8)0.6094 (3)0.17141 (13)0.0291 (9)
H6O0.9906040.5744230.1965220.044*
O70.8509 (6)0.9449 (3)0.02061 (14)0.0257 (9)
O81.0449 (7)0.9278 (3)0.08221 (15)0.0318 (11)
H8O1.0017820.9891280.0892980.048*
S1S0.9985 (3)1.23776 (12)0.17812 (5)0.0329 (4)
C1SA0.8146 (18)1.3285 (11)0.1955 (5)0.108 (6)
H1SA0.6881111.3000800.1860110.130*
H1SB0.8175471.3368380.2295210.130*
H1SC0.8361771.3988960.1807550.130*
C1SB1.1942 (17)1.3168 (10)0.1962 (5)0.092 (5)
H1SD1.1757881.3380650.2288330.111*
H1SE1.3143051.2750980.1932570.111*
H1SF1.2023781.3816840.1766800.111*
O1S0.9905 (8)1.1426 (3)0.21235 (13)0.0329 (10)
S2S1.0039 (3)0.40255 (14)0.25892 (5)0.0349 (4)
C2SA0.8094 (11)0.3687 (7)0.2970 (3)0.0402 (18)
H2SA0.8218680.4097410.3260420.048*
H2SB0.8133560.2911180.3038680.048*
H2SC0.6859250.3865170.2819490.048*
C2SB1.1931 (10)0.3767 (7)0.2993 (3)0.0385 (17)
H2SD1.1744050.4213490.3271720.046*
H2SE1.3180790.3942210.2849540.046*
H2SF1.1913430.3001230.3081180.046*
O2S0.9969 (9)0.5214 (4)0.25197 (15)0.0396 (11)
S3S0.9899 (3)1.19353 (10)0.05375 (5)0.0253 (3)
C3SA0.7711 (10)1.2660 (6)0.0640 (2)0.0304 (14)
H3SA0.7804171.3046370.0937300.036*
H3SB0.6621831.2151650.0651770.036*
H3SC0.7501001.3179390.0386950.036*
C3SB1.1622 (10)1.2955 (5)0.0647 (3)0.0321 (14)
H3SD1.2927781.2645130.0632890.039*
H3SE1.1398761.3262640.0957090.039*
H3SF1.1498461.3524570.0411060.039*
O3S1.0051 (8)1.1197 (3)0.09775 (13)0.0292 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.024 (2)0.017 (2)0.024 (2)0.0024 (18)0.0016 (18)0.0032 (18)
C20.027 (3)0.017 (2)0.022 (2)0.001 (2)0.002 (2)0.0006 (19)
C30.024 (3)0.019 (2)0.019 (2)0.000 (2)0.001 (2)0.0011 (18)
C3A0.020 (3)0.019 (2)0.018 (2)0.002 (2)0.004 (2)0.0005 (18)
C40.024 (3)0.019 (2)0.018 (2)0.001 (2)0.002 (2)0.0015 (18)
C50.025 (3)0.018 (2)0.022 (3)0.002 (2)0.001 (2)0.002 (2)
C5A0.020 (2)0.018 (2)0.020 (2)0.0003 (19)0.0008 (19)0.0016 (19)
N60.024 (2)0.019 (2)0.023 (2)0.0022 (18)0.0005 (18)0.0005 (18)
C70.023 (3)0.018 (2)0.020 (2)0.001 (2)0.000 (2)0.0023 (19)
C80.022 (3)0.021 (2)0.022 (2)0.002 (2)0.005 (2)0.002 (2)
C90.022 (3)0.018 (2)0.023 (3)0.001 (2)0.001 (2)0.000 (2)
C9A0.017 (2)0.017 (2)0.024 (2)0.0007 (19)0.001 (2)0.003 (2)
C1A0.023 (3)0.014 (2)0.025 (3)0.002 (2)0.002 (2)0.000 (2)
C100.032 (3)0.023 (3)0.028 (3)0.004 (2)0.008 (2)0.004 (2)
C110.031 (3)0.027 (3)0.022 (2)0.001 (2)0.000 (2)0.004 (2)
C120.029 (3)0.014 (2)0.022 (2)0.003 (2)0.003 (2)0.0006 (19)
O10.067 (4)0.026 (2)0.037 (2)0.013 (2)0.016 (2)0.006 (2)
O20.038 (2)0.0217 (18)0.0248 (18)0.002 (2)0.002 (2)0.0037 (14)
O30.038 (2)0.0247 (19)0.0236 (18)0.001 (2)0.001 (2)0.0071 (14)
O40.037 (2)0.0177 (19)0.027 (2)0.0019 (17)0.0022 (18)0.0025 (16)
O50.052 (3)0.020 (2)0.027 (2)0.000 (2)0.000 (2)0.0025 (17)
O60.043 (3)0.0227 (19)0.0214 (17)0.002 (2)0.002 (2)0.0032 (14)
O70.029 (2)0.021 (2)0.027 (2)0.0032 (16)0.0031 (17)0.0016 (17)
O80.046 (3)0.0165 (19)0.033 (2)0.0039 (18)0.013 (2)0.0047 (16)
S1S0.0401 (9)0.0298 (7)0.0289 (7)0.0069 (8)0.0017 (8)0.0033 (5)
C1SA0.083 (9)0.098 (10)0.144 (12)0.052 (8)0.064 (8)0.085 (9)
C1SB0.078 (8)0.070 (8)0.129 (11)0.045 (6)0.057 (7)0.056 (8)
O1S0.048 (3)0.0250 (19)0.0251 (18)0.008 (2)0.001 (2)0.0046 (15)
S2S0.0341 (8)0.0470 (9)0.0235 (6)0.0043 (8)0.0032 (7)0.0115 (6)
C2SA0.034 (4)0.047 (4)0.040 (4)0.005 (3)0.007 (3)0.013 (4)
C2SB0.031 (3)0.055 (5)0.030 (4)0.001 (3)0.001 (3)0.012 (3)
O2S0.052 (3)0.040 (2)0.027 (2)0.003 (3)0.004 (2)0.0009 (17)
S3S0.0304 (7)0.0186 (6)0.0267 (6)0.0023 (6)0.0001 (7)0.0035 (5)
C3SA0.027 (3)0.029 (3)0.035 (3)0.001 (3)0.000 (3)0.001 (3)
C3SB0.028 (3)0.023 (3)0.045 (4)0.001 (3)0.001 (3)0.006 (3)
O3S0.042 (2)0.0189 (18)0.0265 (19)0.000 (2)0.004 (2)0.0004 (14)
Geometric parameters (Å, º) top
N1—C1A1.356 (7)O6—H6O0.8400
N1—C21.386 (7)O8—H8O0.8400
N1—H1N0.96 (7)S1S—O1S1.533 (4)
C2—C31.375 (7)S1S—C1SB1.746 (10)
C2—C101.474 (8)S1S—C1SA1.766 (11)
C3—C3A1.425 (7)C1SA—H1SA0.9800
C3—H30.9500C1SA—H1SB0.9800
C3A—C1A1.409 (7)C1SA—H1SC0.9800
C3A—C41.449 (7)C1SB—H1SD0.9800
C4—O31.217 (6)C1SB—H1SE0.9800
C4—C51.563 (7)C1SB—H1SF0.9800
C5—O41.207 (7)S2S—O2S1.484 (5)
C5—C5A1.515 (7)S2S—C2SB1.775 (7)
C5A—N61.342 (7)S2S—C2SA1.780 (8)
C5A—C9A1.415 (7)C2SA—H2SA0.9800
N6—C71.343 (7)C2SA—H2SB0.9800
C7—C81.401 (7)C2SA—H2SC0.9800
C7—C111.516 (7)C2SB—H2SD0.9800
C8—C91.391 (8)C2SB—H2SE0.9800
C8—H80.9500C2SB—H2SF0.9800
C9—C9A1.424 (7)S3S—O3S1.561 (4)
C9—C121.525 (7)S3S—C3SB1.762 (7)
C9A—C1A1.455 (8)S3S—C3SA1.780 (7)
C10—O11.215 (8)C3SA—H3SA0.9800
C10—O21.327 (7)C3SA—H3SB0.9800
C11—O51.223 (7)C3SA—H3SC0.9800
C11—O61.308 (7)C3SB—H3SD0.9800
C12—O71.239 (7)C3SB—H3SE0.9800
C12—O81.275 (7)C3SB—H3SF0.9800
O2—H2O0.8400
C1A—N1—C2110.4 (5)C11—O6—H6O109.5
C1A—N1—H1N122 (4)C12—O8—H8O109.5
C2—N1—H1N127 (4)O1S—S1S—C1SB105.5 (4)
C3—C2—N1108.5 (5)O1S—S1S—C1SA106.3 (4)
C3—C2—C10133.4 (5)C1SB—S1S—C1SA96.6 (7)
N1—C2—C10118.1 (5)S1S—C1SA—H1SA109.5
C2—C3—C3A106.3 (4)S1S—C1SA—H1SB109.5
C2—C3—H3126.8H1SA—C1SA—H1SB109.5
C3A—C3—H3126.8S1S—C1SA—H1SC109.5
C1A—C3A—C3108.2 (4)H1SA—C1SA—H1SC109.5
C1A—C3A—C4122.5 (5)H1SB—C1SA—H1SC109.5
C3—C3A—C4129.2 (5)S1S—C1SB—H1SD109.5
O3—C4—C3A126.1 (5)S1S—C1SB—H1SE109.5
O3—C4—C5119.4 (5)H1SD—C1SB—H1SE109.5
C3A—C4—C5114.5 (4)S1S—C1SB—H1SF109.5
O4—C5—C5A122.5 (5)H1SD—C1SB—H1SF109.5
O4—C5—C4118.4 (5)H1SE—C1SB—H1SF109.5
C5A—C5—C4119.1 (4)O2S—S2S—C2SB106.9 (4)
N6—C5A—C9A125.1 (5)O2S—S2S—C2SA106.9 (4)
N6—C5A—C5113.7 (5)C2SB—S2S—C2SA96.4 (3)
C9A—C5A—C5121.2 (5)S2S—C2SA—H2SA109.5
C5A—N6—C7117.4 (5)S2S—C2SA—H2SB109.5
N6—C7—C8122.5 (5)H2SA—C2SA—H2SB109.5
N6—C7—C11117.5 (5)S2S—C2SA—H2SC109.5
C8—C7—C11120.0 (5)H2SA—C2SA—H2SC109.5
C9—C8—C7120.1 (5)H2SB—C2SA—H2SC109.5
C9—C8—H8119.9S2S—C2SB—H2SD109.5
C7—C8—H8119.9S2S—C2SB—H2SE109.5
C8—C9—C9A118.5 (5)H2SD—C2SB—H2SE109.5
C8—C9—C12114.9 (5)S2S—C2SB—H2SF109.5
C9A—C9—C12126.6 (5)H2SD—C2SB—H2SF109.5
C5A—C9A—C9116.3 (5)H2SE—C2SB—H2SF109.5
C5A—C9A—C1A117.2 (5)O3S—S3S—C3SB103.3 (3)
C9—C9A—C1A126.5 (5)O3S—S3S—C3SA102.6 (3)
N1—C1A—C3A106.5 (5)C3SB—S3S—C3SA100.5 (3)
N1—C1A—C9A128.8 (5)S3S—C3SA—H3SA109.5
C3A—C1A—C9A124.5 (5)S3S—C3SA—H3SB109.5
O1—C10—O2125.6 (5)H3SA—C3SA—H3SB109.5
O1—C10—C2121.4 (5)S3S—C3SA—H3SC109.5
O2—C10—C2113.0 (5)H3SA—C3SA—H3SC109.5
O5—C11—O6125.1 (5)H3SB—C3SA—H3SC109.5
O5—C11—C7122.0 (5)S3S—C3SB—H3SD109.5
O6—C11—C7112.8 (5)S3S—C3SB—H3SE109.5
O7—C12—O8124.7 (5)H3SD—C3SB—H3SE109.5
O7—C12—C9121.5 (5)S3S—C3SB—H3SF109.5
O8—C12—C9113.7 (5)H3SD—C3SB—H3SF109.5
C10—O2—H2O109.5H3SE—C3SB—H3SF109.5
C1A—N1—C2—C30.3 (7)N6—C5A—C9A—C1A178.4 (5)
C1A—N1—C2—C10178.9 (5)C5—C5A—C9A—C1A1.1 (8)
N1—C2—C3—C3A0.1 (7)C8—C9—C9A—C5A1.8 (8)
C10—C2—C3—C3A179.0 (6)C12—C9—C9A—C5A177.2 (5)
C2—C3—C3A—C1A0.1 (7)C8—C9—C9A—C1A174.8 (5)
C2—C3—C3A—C4176.5 (6)C12—C9—C9A—C1A6.2 (9)
C1A—C3A—C4—O3178.7 (6)C2—N1—C1A—C3A0.4 (6)
C3—C3A—C4—O35.3 (11)C2—N1—C1A—C9A176.4 (5)
C1A—C3A—C4—C52.6 (8)C3—C3A—C1A—N10.3 (6)
C3—C3A—C4—C5173.3 (6)C4—C3A—C1A—N1177.0 (5)
O3—C4—C5—O49.2 (9)C3—C3A—C1A—C9A176.5 (5)
C3A—C4—C5—O4169.6 (5)C4—C3A—C1A—C9A6.8 (9)
O3—C4—C5—C5A171.7 (6)C5A—C9A—C1A—N1175.9 (5)
C3A—C4—C5—C5A9.5 (8)C9—C9A—C1A—N17.5 (9)
O4—C5—C5A—N611.2 (8)C5A—C9A—C1A—C3A8.8 (8)
C4—C5—C5A—N6169.7 (5)C9—C9A—C1A—C3A167.9 (6)
O4—C5—C5A—C9A171.2 (5)C3—C2—C10—O1175.0 (7)
C4—C5—C5A—C9A7.8 (8)N1—C2—C10—O14.1 (9)
C9A—C5A—N6—C72.6 (8)C3—C2—C10—O24.3 (10)
C5—C5A—N6—C7174.9 (5)N1—C2—C10—O2176.6 (5)
C5A—N6—C7—C80.5 (8)N6—C7—C11—O59.9 (9)
C5A—N6—C7—C11178.1 (5)C8—C7—C11—O5171.5 (6)
N6—C7—C8—C92.7 (9)N6—C7—C11—O6171.5 (5)
C11—C7—C8—C9178.7 (5)C8—C7—C11—O67.2 (8)
C7—C8—C9—C9A3.7 (8)C8—C9—C12—O7143.3 (6)
C7—C8—C9—C12175.4 (5)C9A—C9—C12—O735.7 (9)
N6—C5A—C9A—C91.4 (8)C8—C9—C12—O833.0 (7)
C5—C5A—C9A—C9175.9 (5)C9A—C9—C12—O8148.0 (6)
 

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