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A new monoclinic (P21/c) polymorph of the title compound has the same overall conformation as a previously reported (Cc) form with the exception of the conformation of the outer hy­droxy H atom. This difference results in very different crystal packing based on hydrogen bonding, i.e. supra­molecular tubes in the new form as opposed to a three-dimensional architecture in the Cc form.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989014026498/su5033sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989014026498/su5033Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989014026498/su5033Isup3.cml
Supplementary material

CCDC reference: 960620

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.035
  • wR factor = 0.086
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 2 Report
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 0 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2008), PLATON (Spek, 2009 and publCIF (Westrip, 2010).

2,4-Dihydroxybenzaldehyde 4-methylthiosemicarbazone top
Crystal data top
C9H11N3O2SF(000) = 472
Mr = 225.27Dx = 1.496 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.3058 (2) ÅCell parameters from 3917 reflections
b = 6.0582 (1) Åθ = 3.3–29.8°
c = 22.6041 (6) ŵ = 0.31 mm1
β = 91.100 (2)°T = 100 K
V = 1000.27 (4) Å3Block, colourless
Z = 40.48 × 0.19 × 0.14 mm
Data collection top
Bruker APEXII CCD
diffractometer
2302 independent reflections
Radiation source: sealed tube1950 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.866, Tmax = 0.957k = 77
9696 measured reflectionsl = 2924
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0336P)2 + 0.7405P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
2302 reflectionsΔρmax = 0.30 e Å3
153 parametersΔρmin = 0.31 e Å3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.15271 (5)1.11056 (7)1.14702 (2)0.01707 (12)
O10.33247 (16)0.2527 (2)1.00557 (5)0.0174 (3)
H1o0.301 (3)0.362 (4)1.0247 (11)0.044 (7)*
O20.45517 (16)0.0527 (2)0.80619 (5)0.0204 (3)
H2o0.541 (3)0.033 (4)0.8232 (11)0.051 (7)*
N10.15573 (18)0.6695 (2)1.14178 (6)0.0148 (3)
H1n0.153 (3)0.557 (3)1.1220 (9)0.019 (5)*
N20.15295 (18)0.8552 (2)1.05291 (6)0.0152 (3)
H2n0.183 (3)0.984 (4)1.0359 (9)0.029 (5)*
N30.19726 (17)0.6617 (2)1.02301 (6)0.0139 (3)
C10.1544 (2)0.8599 (3)1.11312 (7)0.0135 (3)
C20.1526 (2)0.6471 (3)1.20604 (7)0.0197 (4)
H2A0.26990.69681.22310.030*
H2B0.13260.49201.21640.030*
H2C0.05340.73741.22170.030*
C30.1997 (2)0.6841 (3)0.96619 (7)0.0141 (3)
H30.15920.81970.94940.017*
C40.2616 (2)0.5119 (3)0.92679 (7)0.0137 (3)
C50.3302 (2)0.3078 (3)0.94674 (7)0.0135 (3)
C60.3978 (2)0.1534 (3)0.90734 (7)0.0154 (3)
H60.44610.01730.92140.019*
C70.3941 (2)0.1999 (3)0.84699 (7)0.0157 (3)
C80.3264 (2)0.4006 (3)0.82584 (7)0.0177 (3)
H80.32390.43120.78460.021*
C90.2630 (2)0.5540 (3)0.86554 (7)0.0168 (3)
H90.21920.69200.85120.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0239 (2)0.0115 (2)0.0158 (2)0.00296 (15)0.00059 (15)0.00209 (15)
O10.0274 (6)0.0135 (6)0.0114 (6)0.0017 (5)0.0029 (5)0.0007 (5)
O20.0214 (6)0.0243 (7)0.0154 (6)0.0041 (5)0.0010 (5)0.0062 (5)
N10.0223 (7)0.0099 (7)0.0120 (7)0.0017 (5)0.0015 (5)0.0019 (6)
N20.0215 (7)0.0103 (7)0.0137 (7)0.0012 (5)0.0019 (5)0.0007 (5)
N30.0163 (6)0.0116 (6)0.0139 (7)0.0005 (5)0.0011 (5)0.0023 (5)
C10.0119 (7)0.0145 (8)0.0141 (8)0.0005 (6)0.0004 (6)0.0009 (6)
C20.0279 (9)0.0177 (8)0.0137 (8)0.0017 (7)0.0020 (6)0.0019 (7)
C30.0144 (7)0.0125 (7)0.0153 (8)0.0008 (6)0.0001 (6)0.0006 (6)
C40.0140 (7)0.0143 (8)0.0129 (7)0.0016 (6)0.0011 (6)0.0002 (6)
C50.0145 (7)0.0150 (8)0.0110 (7)0.0036 (6)0.0004 (5)0.0005 (6)
C60.0150 (7)0.0136 (8)0.0177 (8)0.0006 (6)0.0018 (6)0.0009 (6)
C70.0139 (7)0.0180 (8)0.0152 (8)0.0016 (6)0.0025 (6)0.0043 (6)
C80.0184 (7)0.0240 (9)0.0106 (7)0.0022 (6)0.0006 (6)0.0008 (7)
C90.0163 (7)0.0187 (8)0.0153 (8)0.0008 (6)0.0005 (6)0.0027 (7)
Geometric parameters (Å, º) top
S1—C11.7011 (16)C2—H2B0.9800
O1—C51.3707 (19)C2—H2C0.9800
O1—H1o0.83 (3)C3—C41.449 (2)
O2—C71.3640 (19)C3—H30.9500
O2—H2o0.90 (3)C4—C51.405 (2)
N1—C11.323 (2)C4—C91.408 (2)
N1—C21.459 (2)C5—C61.389 (2)
N1—H1n0.81 (2)C6—C71.393 (2)
N2—C11.361 (2)C6—H60.9500
N2—N31.3945 (18)C7—C81.394 (2)
N2—H2n0.90 (2)C8—C91.378 (2)
N3—C31.292 (2)C8—H80.9500
C2—H2A0.9800C9—H90.9500
C5—O1—H1o108.3 (17)C4—C3—H3118.5
C7—O2—H2o108.9 (16)C5—C4—C9117.76 (14)
C1—N1—C2124.63 (14)C5—C4—C3123.32 (14)
C1—N1—H1n117.4 (14)C9—C4—C3118.82 (14)
C2—N1—H1n117.9 (14)O1—C5—C6117.41 (14)
C1—N2—N3120.33 (13)O1—C5—C4121.55 (14)
C1—N2—H2n114.2 (13)C6—C5—C4121.04 (14)
N3—N2—H2n117.6 (13)C5—C6—C7119.46 (15)
C3—N3—N2113.67 (13)C5—C6—H6120.3
N1—C1—N2118.11 (14)C7—C6—H6120.3
N1—C1—S1123.91 (12)O2—C7—C6122.00 (15)
N2—C1—S1117.98 (12)O2—C7—C8117.19 (14)
N1—C2—H2A109.5C6—C7—C8120.81 (14)
N1—C2—H2B109.5C9—C8—C7119.10 (15)
H2A—C2—H2B109.5C9—C8—H8120.4
N1—C2—H2C109.5C7—C8—H8120.4
H2A—C2—H2C109.5C8—C9—C4121.80 (15)
H2B—C2—H2C109.5C8—C9—H9119.1
N3—C3—C4123.08 (15)C4—C9—H9119.1
N3—C3—H3118.5
C1—N2—N3—C3176.54 (14)C3—C4—C5—C6176.13 (14)
C2—N1—C1—N2178.35 (14)O1—C5—C6—C7178.45 (13)
C2—N1—C1—S11.2 (2)C4—C5—C6—C71.3 (2)
N3—N2—C1—N115.6 (2)C5—C6—C7—O2178.64 (14)
N3—N2—C1—S1164.83 (11)C5—C6—C7—C81.1 (2)
N2—N3—C3—C4173.05 (13)O2—C7—C8—C9179.92 (14)
N3—C3—C4—C52.2 (2)C6—C7—C8—C90.2 (2)
N3—C3—C4—C9178.56 (14)C7—C8—C9—C41.3 (2)
C9—C4—C5—O1179.49 (14)C5—C4—C9—C81.0 (2)
C3—C4—C5—O14.1 (2)C3—C4—C9—C8177.60 (14)
C9—C4—C5—C60.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···N30.83 (2)1.97 (2)2.6992 (17)147 (2)
N1—H1n···N30.815 (19)2.35 (2)2.7080 (19)107.1 (16)
O2—H2o···S1i0.90 (2)2.37 (2)3.1918 (12)152 (2)
N1—H1n···S1ii0.815 (19)2.763 (18)3.3883 (13)134.9 (17)
N2—H2n···O1iii0.90 (2)2.08 (2)2.9527 (17)162 (2)
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y1, z; (iii) x, y+1, z.
 

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