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Crystal structures of three co-crystals of 1,2-bis­(pyridin-4-yl)ethane with 4-alk­oxy­benzoic acids have been determined. The asymmetric unit of each compound comprises two crystallographically independent acid mol­ecules and one base mol­ecule, which are held together by O—H...N hydrogen bonds, forming linear hydrogen-bonded 2:1 units.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015019349/su5225sup1.cif
Contains datablocks I, II, III, General

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989015019349/su5225Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989015019349/su5225IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989015019349/su5225IIIsup4.hkl
Contains datablock III

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015019349/su5225Isup5.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015019349/su5225IIsup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015019349/su5225IIIsup7.cml
Supplementary material

CCDC references: 1430875; 1430874; 1430873

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.001 Å
  • Mean [sigma](C-C) = 0.002 Å
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.113
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 3 Report
Alert level G PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 2 Note C9 H10 O3 PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 3 Report PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 5 Note
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 4 ALERT level G = General information/check it is not something unexpected 1 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 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Datablock: II
Alert level C PLAT355_ALERT_3_C Long O-H (X0.82,N0.98A) O4 - H4 .. 1.01 Ang. PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.306 Check PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Th(Min) ... 8 Report PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 4 Report
Alert level G PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT112_ALERT_2_G ADDSYM Detects Additional (Pseudo) Symm. Elem... sub Check PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 2 Note C10 H12 O3 PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 3 Note C10 H12 O3 PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 14 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Datablock: III

Alert level B PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers .... 6 Check
Alert level C PLAT355_ALERT_3_C Long O-H (X0.82,N0.98A) O1 - H1 .. 1.02 Ang. PLAT355_ALERT_3_C Long O-H (X0.82,N0.98A) O4 - H4 .. 1.03 Ang. PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 4.362 Check PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Th(Min) ... 10 Report PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 28 Report
Alert level G PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 2 Note C11 H14 O3 PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 44 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 5 ALERT level C = Check. Ensure it is not caused by an omission or oversight 2 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 6 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

For all compounds, data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: Il Milione (Burla et al., 2007); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: CrystalStructure (Rigaku, 2010) and PLATON (Spek, 2009).

(I) 4-Ethoxybenzoic acid–1,2-bis(pyridin-4-yl)ethane (2/1) top
Crystal data top
2C9H10O3·C12H12N2Z = 1
Mr = 516.57F(000) = 274.00
Triclinic, P1Dx = 1.346 Mg m3
a = 6.967 (3) ÅMo Kα radiation, λ = 0.71075 Å
b = 9.163 (4) ÅCell parameters from 7263 reflections
c = 10.813 (6) Åθ = 3.1–30.0°
α = 75.41 (2)°µ = 0.09 mm1
β = 74.97 (2)°T = 93 K
γ = 77.801 (19)°Block, colorless
V = 637.3 (6) Å30.42 × 0.38 × 0.36 mm
Data collection top
Rigaku R-AXIS RAPIDII
diffractometer
2628 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm-1Rint = 0.014
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 98
Tmin = 0.877, Tmax = 0.967k = 1111
6408 measured reflectionsl = 1414
2908 independent reflections
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)] = 0.038Hydrogen site location: mixed
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0808P)2 + 0.0636P]
where P = (Fo2 + 2Fc2)/3
2908 reflections(Δ/σ)max < 0.001
177 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.40 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.

Refinement. Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.08950 (10)0.17801 (7)0.27364 (6)0.01773 (17)
O20.36783 (10)0.14762 (7)0.11743 (7)0.02284 (18)
O30.30648 (10)0.53714 (7)0.43129 (6)0.01635 (17)
N10.08580 (11)0.46999 (8)0.17005 (7)0.01554 (18)
C10.25803 (12)0.07314 (9)0.26753 (8)0.01328 (19)
C20.12341 (13)0.13188 (10)0.38081 (8)0.01439 (19)
H20.01750.06450.42230.017*
C30.14273 (13)0.28698 (9)0.43308 (8)0.01467 (19)
H30.05110.32580.51040.018*
C40.29770 (13)0.38638 (9)0.37165 (8)0.01337 (19)
C50.42960 (12)0.32990 (9)0.25669 (8)0.01389 (19)
H50.53260.39760.21350.017*
C60.40911 (12)0.17344 (9)0.20570 (8)0.01382 (19)
H60.49940.13460.12770.017*
C70.24541 (13)0.09388 (10)0.21156 (8)0.01440 (19)
C80.46043 (13)0.64340 (10)0.36946 (9)0.0164 (2)
H8A0.59470.61720.36090.020*
H8B0.44210.63950.28080.020*
C90.44480 (14)0.80100 (10)0.45311 (10)0.0199 (2)
H9A0.46090.80320.54100.030*
H9B0.55060.87530.41360.030*
H9C0.31280.82690.45910.030*
C100.21117 (14)0.51152 (10)0.05431 (9)0.0174 (2)
H100.30310.43430.01590.021*
C110.21180 (13)0.66206 (10)0.01116 (8)0.0168 (2)
H110.30380.68650.09240.020*
C120.07739 (13)0.77805 (9)0.04216 (8)0.01326 (19)
C130.05253 (12)0.73458 (9)0.16120 (8)0.01421 (19)
H130.14790.80930.20100.017*
C140.04226 (12)0.58080 (9)0.22195 (8)0.01511 (19)
H140.13050.55330.30430.018*
C150.08332 (12)0.94192 (9)0.02916 (8)0.01380 (19)
H15A0.07600.95040.12100.017*
H15B0.21450.96860.03080.017*
H10.091 (2)0.285 (2)0.2343 (17)0.060 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0214 (3)0.0103 (3)0.0183 (3)0.0011 (2)0.0008 (2)0.0020 (2)
O20.0258 (4)0.0134 (3)0.0224 (4)0.0043 (3)0.0035 (3)0.0005 (2)
O30.0206 (3)0.0087 (3)0.0158 (3)0.0015 (2)0.0006 (2)0.0005 (2)
N10.0183 (4)0.0113 (3)0.0182 (4)0.0028 (3)0.0076 (3)0.0011 (3)
C10.0161 (4)0.0112 (4)0.0135 (4)0.0030 (3)0.0053 (3)0.0014 (3)
C20.0165 (4)0.0128 (4)0.0139 (4)0.0016 (3)0.0027 (3)0.0039 (3)
C30.0171 (4)0.0138 (4)0.0119 (4)0.0037 (3)0.0008 (3)0.0018 (3)
C40.0160 (4)0.0105 (4)0.0139 (4)0.0026 (3)0.0053 (3)0.0007 (3)
C50.0141 (4)0.0122 (4)0.0150 (4)0.0006 (3)0.0035 (3)0.0030 (3)
C60.0138 (4)0.0143 (4)0.0125 (4)0.0037 (3)0.0022 (3)0.0008 (3)
C70.0168 (4)0.0128 (4)0.0144 (4)0.0027 (3)0.0048 (3)0.0025 (3)
C80.0167 (4)0.0116 (4)0.0189 (4)0.0000 (3)0.0035 (3)0.0021 (3)
C90.0234 (4)0.0114 (4)0.0241 (5)0.0029 (3)0.0075 (4)0.0004 (3)
C100.0220 (4)0.0125 (4)0.0175 (4)0.0009 (3)0.0050 (3)0.0037 (3)
C110.0205 (4)0.0134 (4)0.0145 (4)0.0024 (3)0.0020 (3)0.0016 (3)
C120.0147 (4)0.0115 (4)0.0151 (4)0.0029 (3)0.0070 (3)0.0009 (3)
C130.0132 (4)0.0116 (4)0.0169 (4)0.0010 (3)0.0035 (3)0.0019 (3)
C140.0152 (4)0.0128 (4)0.0163 (4)0.0036 (3)0.0042 (3)0.0008 (3)
C150.0152 (4)0.0106 (4)0.0142 (4)0.0026 (3)0.0031 (3)0.0002 (3)
Geometric parameters (Å, º) top
O1—C71.3242 (11)C8—C91.5076 (13)
O1—H10.970 (19)C8—H8A0.9900
O2—C71.2169 (12)C8—H8B0.9900
O3—C41.3653 (11)C9—H9A0.9800
O3—C81.4353 (11)C9—H9B0.9800
N1—C141.3365 (12)C9—H9C0.9800
N1—C101.3445 (13)C10—C111.3831 (13)
C1—C61.3912 (12)C10—H100.9500
C1—C21.3983 (13)C11—C121.3954 (12)
C1—C71.4900 (13)C11—H110.9500
C2—C31.3825 (13)C12—C131.3874 (14)
C2—H20.9500C12—C151.5091 (13)
C3—C41.3978 (12)C13—C141.3920 (12)
C3—H30.9500C13—H130.9500
C4—C51.3936 (14)C14—H140.9500
C5—C61.3913 (12)C15—C15i1.5215 (16)
C5—H50.9500C15—H15A0.9900
C6—H60.9500C15—H15B0.9900
C7—O1—H1110.2 (10)H8A—C8—H8B108.4
C4—O3—C8117.24 (7)C8—C9—H9A109.5
C14—N1—C10117.48 (8)C8—C9—H9B109.5
C6—C1—C2119.07 (8)H9A—C9—H9B109.5
C6—C1—C7118.99 (8)C8—C9—H9C109.5
C2—C1—C7121.94 (8)H9A—C9—H9C109.5
C3—C2—C1120.72 (8)H9B—C9—H9C109.5
C3—C2—H2119.6N1—C10—C11122.73 (8)
C1—C2—H2119.6N1—C10—H10118.6
C2—C3—C4119.69 (8)C11—C10—H10118.6
C2—C3—H3120.2C10—C11—C12120.01 (9)
C4—C3—H3120.2C10—C11—H11120.0
O3—C4—C5124.27 (8)C12—C11—H11120.0
O3—C4—C3115.52 (8)C13—C12—C11117.06 (8)
C5—C4—C3120.21 (8)C13—C12—C15123.64 (8)
C6—C5—C4119.43 (8)C11—C12—C15119.28 (8)
C6—C5—H5120.3C12—C13—C14119.55 (8)
C4—C5—H5120.3C12—C13—H13120.2
C1—C6—C5120.84 (8)C14—C13—H13120.2
C1—C6—H6119.6N1—C14—C13123.16 (8)
C5—C6—H6119.6N1—C14—H14118.4
O2—C7—O1123.25 (9)C13—C14—H14118.4
O2—C7—C1122.84 (8)C12—C15—C15i115.14 (9)
O1—C7—C1113.92 (8)C12—C15—H15A108.5
O3—C8—C9108.07 (8)C15i—C15—H15A108.5
O3—C8—H8A110.1C12—C15—H15B108.5
C9—C8—H8A110.1C15i—C15—H15B108.5
O3—C8—H8B110.1H15A—C15—H15B107.5
C9—C8—H8B110.1
C6—C1—C2—C31.73 (13)C6—C1—C7—O1176.33 (7)
C7—C1—C2—C3177.82 (7)C2—C1—C7—O14.12 (12)
C1—C2—C3—C40.40 (13)C4—O3—C8—C9178.74 (7)
C8—O3—C4—C50.98 (12)C14—N1—C10—C110.07 (13)
C8—O3—C4—C3178.48 (7)N1—C10—C11—C120.53 (14)
C2—C3—C4—O3179.15 (7)C10—C11—C12—C130.12 (13)
C2—C3—C4—C51.37 (13)C10—C11—C12—C15178.65 (8)
O3—C4—C5—C6178.79 (7)C11—C12—C13—C140.71 (12)
C3—C4—C5—C61.78 (13)C15—C12—C13—C14177.75 (7)
C2—C1—C6—C51.31 (13)C10—N1—C14—C130.83 (12)
C7—C1—C6—C5178.25 (7)C12—C13—C14—N11.24 (13)
C4—C5—C6—C10.43 (13)C13—C12—C15—C15i7.83 (14)
C6—C1—C7—O23.77 (13)C11—C12—C15—C15i173.74 (8)
C2—C1—C7—O2175.77 (8)
Symmetry code: (i) x, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.967 (18)1.659 (18)2.6247 (17)178.0 (14)
C6—H6···O2ii0.952.603.406 (2)144
Symmetry code: (ii) x+1, y, z.
(II) 4-n-Propoxybenzoic acid–1,2-bis(pyridin-4-yl)ethane (2/1) top
Crystal data top
2C10H12O3·C12H12N2Z = 2
Mr = 544.63F(000) = 580.00
Triclinic, P1Dx = 1.302 Mg m3
a = 9.121 (3) ÅMo Kα radiation, λ = 0.71075 Å
b = 12.552 (5) ÅCell parameters from 12886 reflections
c = 13.306 (6) Åθ = 3.0–30.1°
α = 71.328 (16)°µ = 0.09 mm1
β = 75.076 (18)°T = 290 K
γ = 89.817 (16)°Block, colorless
V = 1389.2 (9) Å30.40 × 0.30 × 0.20 mm
Data collection top
Rigaku R-AXIS RAPIDII
diffractometer
4294 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm-1Rint = 0.022
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1111
Tmin = 0.601, Tmax = 0.982k = 1616
14034 measured reflectionsl = 1717
6347 independent reflections
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)] = 0.041Hydrogen site location: mixed
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 0.97 w = 1/[σ2(Fo2) + (0.0771P)2]
where P = (Fo2 + 2Fc2)/3
6347 reflections(Δ/σ)max = 0.001
371 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.21 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.

Refinement. Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.86106 (9)0.14285 (8)0.69416 (7)0.0513 (2)
O20.85639 (9)0.04844 (8)0.57825 (7)0.0572 (3)
O31.54698 (8)0.05094 (7)0.86644 (7)0.0468 (2)
O40.77073 (9)0.45876 (7)0.19717 (7)0.0492 (2)
O50.76146 (9)0.54551 (8)0.31997 (7)0.0581 (3)
O61.46050 (9)0.64460 (7)0.05092 (6)0.0470 (2)
N10.57003 (10)0.19071 (8)0.59325 (8)0.0432 (2)
N20.47841 (10)0.40765 (8)0.29105 (8)0.0438 (2)
C11.08880 (11)0.04396 (9)0.71057 (8)0.0356 (2)
C21.16087 (12)0.06518 (9)0.80729 (9)0.0386 (2)
H21.10570.10200.83820.046*
C31.31324 (12)0.03204 (9)0.85748 (9)0.0407 (3)
H31.36010.04570.92250.049*
C41.39693 (12)0.02169 (9)0.81125 (9)0.0380 (2)
C51.32604 (12)0.04396 (10)0.71520 (9)0.0407 (3)
H51.38110.08070.68430.049*
C61.17302 (12)0.01094 (9)0.66615 (9)0.0399 (2)
H61.12560.02590.60190.048*
C70.92513 (12)0.07793 (9)0.65432 (9)0.0384 (2)
C81.63612 (12)0.10691 (10)0.82118 (10)0.0449 (3)
H8A1.59290.17640.81640.054*
H8B1.63480.05910.74740.054*
C91.79706 (13)0.13286 (11)0.89263 (10)0.0484 (3)
H9A1.84270.06310.89330.058*
H9B1.79790.17630.96760.058*
C101.88892 (14)0.19964 (12)0.84880 (11)0.0557 (3)
H10A1.84250.26800.84710.084*
H10B1.89120.15520.77560.084*
H10C1.99100.21780.89600.084*
C110.99847 (12)0.55101 (9)0.19183 (9)0.0372 (2)
C121.08279 (12)0.51427 (9)0.10802 (9)0.0407 (3)
H121.03500.46720.08230.049*
C131.23598 (13)0.54654 (10)0.06260 (9)0.0426 (3)
H131.29070.52170.00620.051*
C141.30898 (12)0.61617 (9)0.10086 (9)0.0394 (2)
C151.22638 (12)0.65343 (10)0.18464 (9)0.0436 (3)
H151.27440.69970.21110.052*
C161.07223 (13)0.62128 (10)0.22845 (9)0.0437 (3)
H161.01690.64740.28370.052*
C170.83294 (12)0.51878 (9)0.24279 (9)0.0400 (2)
C181.53914 (13)0.70883 (10)0.09605 (10)0.0467 (3)
H18A1.53250.66590.17220.056*
H18B1.49100.77820.09440.056*
C191.70299 (13)0.73646 (11)0.03172 (10)0.0467 (3)
H19A1.71040.77900.04470.056*
H19B1.75220.66740.03420.056*
C201.78187 (14)0.80588 (11)0.08115 (11)0.0557 (3)
H20A1.77960.76170.15530.084*
H20B1.73000.87250.08130.084*
H20C1.88570.82710.03790.084*
C210.50433 (13)0.14613 (10)0.51637 (10)0.0448 (3)
H210.56420.09870.49870.054*
C220.35180 (12)0.16703 (10)0.46180 (10)0.0443 (3)
H220.31080.13360.40880.053*
C230.25902 (12)0.23753 (9)0.48532 (9)0.0369 (2)
C240.32816 (13)0.28490 (11)0.56375 (10)0.0494 (3)
H240.27150.33390.58190.059*
C250.48225 (13)0.25931 (12)0.61548 (10)0.0543 (3)
H250.52650.29190.66850.065*
C260.41740 (13)0.43030 (11)0.38378 (10)0.0474 (3)
H260.48030.46490.41140.057*
C270.26572 (13)0.40488 (10)0.44034 (10)0.0459 (3)
H270.22840.42200.50480.055*
C280.16865 (11)0.35392 (9)0.40132 (9)0.0376 (2)
C290.23253 (12)0.32884 (10)0.30641 (9)0.0424 (3)
H290.17280.29260.27800.051*
C300.38599 (13)0.35788 (10)0.25382 (10)0.0453 (3)
H300.42640.34170.18920.054*
C310.09183 (12)0.25894 (10)0.42528 (9)0.0401 (3)
H31A0.08180.29460.34720.048*
H31B0.04890.18670.43470.048*
C320.00142 (12)0.33167 (10)0.46139 (9)0.0406 (3)
H32A0.04200.40370.45240.049*
H32B0.00840.29580.53940.049*
H10.755 (2)0.1609 (15)0.6535 (14)0.098 (6)*
H40.658 (2)0.4399 (16)0.2335 (15)0.106 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0343 (4)0.0726 (6)0.0542 (5)0.0057 (4)0.0016 (4)0.0386 (5)
O20.0386 (4)0.0833 (6)0.0575 (5)0.0022 (4)0.0016 (4)0.0451 (5)
O30.0326 (4)0.0641 (5)0.0447 (5)0.0036 (4)0.0004 (3)0.0273 (4)
O40.0359 (4)0.0656 (5)0.0546 (5)0.0020 (4)0.0107 (4)0.0324 (4)
O50.0434 (5)0.0806 (6)0.0562 (5)0.0068 (4)0.0011 (4)0.0401 (5)
O60.0368 (4)0.0590 (5)0.0484 (5)0.0050 (4)0.0037 (3)0.0281 (4)
N10.0339 (5)0.0533 (6)0.0421 (5)0.0010 (4)0.0052 (4)0.0194 (4)
N20.0337 (5)0.0465 (5)0.0497 (6)0.0016 (4)0.0118 (4)0.0135 (5)
C10.0344 (5)0.0373 (5)0.0354 (6)0.0066 (4)0.0080 (4)0.0137 (5)
C20.0375 (5)0.0444 (6)0.0388 (6)0.0037 (5)0.0096 (4)0.0210 (5)
C30.0398 (6)0.0493 (6)0.0350 (6)0.0048 (5)0.0038 (4)0.0217 (5)
C40.0341 (5)0.0408 (6)0.0371 (6)0.0033 (4)0.0051 (4)0.0139 (5)
C50.0367 (5)0.0497 (6)0.0397 (6)0.0000 (5)0.0079 (4)0.0222 (5)
C60.0386 (6)0.0479 (6)0.0354 (6)0.0043 (5)0.0048 (4)0.0209 (5)
C70.0344 (5)0.0447 (6)0.0374 (6)0.0045 (5)0.0071 (4)0.0171 (5)
C80.0373 (6)0.0527 (7)0.0468 (7)0.0009 (5)0.0063 (5)0.0230 (5)
C90.0389 (6)0.0548 (7)0.0466 (7)0.0028 (5)0.0011 (5)0.0184 (6)
C100.0407 (6)0.0621 (8)0.0621 (8)0.0084 (6)0.0018 (6)0.0270 (7)
C110.0370 (5)0.0407 (6)0.0357 (6)0.0032 (4)0.0124 (4)0.0130 (5)
C120.0423 (6)0.0460 (6)0.0399 (6)0.0002 (5)0.0151 (5)0.0194 (5)
C130.0438 (6)0.0503 (6)0.0383 (6)0.0030 (5)0.0088 (5)0.0224 (5)
C140.0380 (5)0.0427 (6)0.0378 (6)0.0026 (5)0.0096 (4)0.0141 (5)
C150.0401 (6)0.0494 (6)0.0469 (6)0.0026 (5)0.0100 (5)0.0251 (5)
C160.0429 (6)0.0510 (7)0.0413 (6)0.0032 (5)0.0073 (5)0.0240 (5)
C170.0390 (6)0.0432 (6)0.0395 (6)0.0040 (5)0.0123 (5)0.0149 (5)
C180.0424 (6)0.0506 (7)0.0512 (7)0.0017 (5)0.0083 (5)0.0256 (6)
C190.0397 (6)0.0505 (7)0.0487 (7)0.0024 (5)0.0066 (5)0.0191 (5)
C200.0434 (6)0.0641 (8)0.0609 (8)0.0070 (6)0.0073 (6)0.0276 (7)
C210.0378 (6)0.0512 (7)0.0484 (7)0.0026 (5)0.0084 (5)0.0229 (5)
C220.0381 (6)0.0529 (7)0.0457 (6)0.0014 (5)0.0045 (5)0.0266 (5)
C230.0332 (5)0.0411 (6)0.0350 (5)0.0034 (4)0.0078 (4)0.0119 (5)
C240.0387 (6)0.0653 (8)0.0511 (7)0.0061 (5)0.0058 (5)0.0332 (6)
C250.0408 (6)0.0771 (9)0.0513 (7)0.0030 (6)0.0006 (5)0.0388 (7)
C260.0393 (6)0.0556 (7)0.0502 (7)0.0022 (5)0.0164 (5)0.0177 (6)
C270.0408 (6)0.0571 (7)0.0428 (6)0.0000 (5)0.0119 (5)0.0202 (5)
C280.0334 (5)0.0388 (6)0.0388 (6)0.0033 (4)0.0103 (4)0.0101 (5)
C290.0356 (5)0.0474 (6)0.0486 (7)0.0004 (5)0.0120 (5)0.0210 (5)
C300.0376 (6)0.0494 (7)0.0489 (7)0.0036 (5)0.0072 (5)0.0200 (5)
C310.0322 (5)0.0482 (6)0.0397 (6)0.0003 (5)0.0050 (4)0.0178 (5)
C320.0342 (5)0.0483 (6)0.0398 (6)0.0008 (5)0.0079 (4)0.0169 (5)
Geometric parameters (Å, º) top
O1—C71.3136 (14)C13—C141.3891 (15)
O1—H10.963 (19)C13—H130.9300
O2—C71.2108 (14)C14—C151.3885 (16)
O3—C41.3638 (13)C15—C161.3821 (16)
O3—C81.4297 (13)C15—H150.9300
O4—C171.3157 (14)C16—H160.9300
O4—H41.01 (2)C18—C191.4969 (16)
O5—C171.2110 (14)C18—H18A0.9700
O6—C141.3628 (13)C18—H18B0.9700
O6—C181.4355 (13)C19—C201.5245 (16)
N1—C251.3264 (15)C19—H19A0.9700
N1—C211.3294 (15)C19—H19B0.9700
N2—C301.3277 (15)C20—H20A0.9600
N2—C261.3352 (16)C20—H20B0.9600
C1—C61.3828 (15)C20—H20C0.9600
C1—C21.3935 (15)C21—C221.3754 (16)
C1—C71.4815 (15)C21—H210.9300
C2—C31.3778 (15)C22—C231.3841 (15)
C2—H20.9300C22—H220.9300
C3—C41.3881 (15)C23—C241.3770 (16)
C3—H30.9300C23—C311.5079 (15)
C4—C51.3897 (16)C24—C251.3840 (16)
C5—C61.3810 (15)C24—H240.9300
C5—H50.9300C25—H250.9300
C6—H60.9300C26—C271.3766 (17)
C8—C91.5002 (16)C26—H260.9300
C8—H8A0.9700C27—C281.3841 (15)
C8—H8B0.9700C27—H270.9300
C9—C101.5211 (16)C28—C291.3812 (16)
C9—H9A0.9700C28—C321.5084 (15)
C9—H9B0.9700C29—C301.3846 (16)
C10—H10A0.9600C29—H290.9300
C10—H10B0.9600C30—H300.9300
C10—H10C0.9600C31—C321.5113 (16)
C11—C161.3842 (15)C31—H31A0.9700
C11—C121.3903 (16)C31—H31B0.9700
C11—C171.4846 (16)C32—H32A0.9700
C12—C131.3761 (16)C32—H32B0.9700
C12—H120.9300
C7—O1—H1109.0 (11)O5—C17—O4122.94 (10)
C4—O3—C8117.37 (9)O5—C17—C11122.69 (10)
C17—O4—H4111.7 (11)O4—C17—C11114.38 (10)
C14—O6—C18116.48 (9)O6—C18—C19110.74 (10)
C25—N1—C21117.15 (10)O6—C18—H18A109.5
C30—N2—C26117.12 (10)C19—C18—H18A109.5
C6—C1—C2118.76 (10)O6—C18—H18B109.5
C6—C1—C7119.13 (10)C19—C18—H18B109.5
C2—C1—C7122.11 (10)H18A—C18—H18B108.1
C3—C2—C1120.48 (10)C18—C19—C20109.14 (10)
C3—C2—H2119.8C18—C19—H19A109.9
C1—C2—H2119.8C20—C19—H19A109.9
C2—C3—C4120.17 (10)C18—C19—H19B109.9
C2—C3—H3119.9C20—C19—H19B109.9
C4—C3—H3119.9H19A—C19—H19B108.3
O3—C4—C3116.02 (10)C19—C20—H20A109.5
O3—C4—C5124.12 (10)C19—C20—H20B109.5
C3—C4—C5119.85 (10)H20A—C20—H20B109.5
C6—C5—C4119.36 (10)C19—C20—H20C109.5
C6—C5—H5120.3H20A—C20—H20C109.5
C4—C5—H5120.3H20B—C20—H20C109.5
C5—C6—C1121.37 (10)N1—C21—C22122.90 (10)
C5—C6—H6119.3N1—C21—H21118.6
C1—C6—H6119.3C22—C21—H21118.6
O2—C7—O1122.92 (10)C21—C22—C23120.34 (11)
O2—C7—C1122.94 (10)C21—C22—H22119.8
O1—C7—C1114.14 (10)C23—C22—H22119.8
O3—C8—C9109.94 (10)C24—C23—C22116.51 (10)
O3—C8—H8A109.7C24—C23—C31123.83 (10)
C9—C8—H8A109.7C22—C23—C31119.66 (10)
O3—C8—H8B109.7C23—C24—C25119.76 (11)
C9—C8—H8B109.7C23—C24—H24120.1
H8A—C8—H8B108.2C25—C24—H24120.1
C8—C9—C10109.84 (10)N1—C25—C24123.33 (11)
C8—C9—H9A109.7N1—C25—H25118.3
C10—C9—H9A109.7C24—C25—H25118.3
C8—C9—H9B109.7N2—C26—C27123.04 (11)
C10—C9—H9B109.7N2—C26—H26118.5
H9A—C9—H9B108.2C27—C26—H26118.5
C9—C10—H10A109.5C26—C27—C28120.05 (11)
C9—C10—H10B109.5C26—C27—H27120.0
H10A—C10—H10B109.5C28—C27—H27120.0
C9—C10—H10C109.5C29—C28—C27116.80 (10)
H10A—C10—H10C109.5C29—C28—C32123.87 (10)
H10B—C10—H10C109.5C27—C28—C32119.32 (10)
C16—C11—C12118.39 (10)C28—C29—C30119.67 (10)
C16—C11—C17118.83 (10)C28—C29—H29120.2
C12—C11—C17122.78 (10)C30—C29—H29120.2
C13—C12—C11120.97 (10)N2—C30—C29123.30 (11)
C13—C12—H12119.5N2—C30—H30118.3
C11—C12—H12119.5C29—C30—H30118.3
C12—C13—C14120.07 (10)C23—C31—C32115.61 (10)
C12—C13—H13120.0C23—C31—H31A108.4
C14—C13—H13120.0C32—C31—H31A108.4
O6—C14—C15124.08 (10)C23—C31—H31B108.4
O6—C14—C13116.27 (10)C32—C31—H31B108.4
C15—C14—C13119.64 (10)H31A—C31—H31B107.4
C16—C15—C14119.53 (10)C28—C32—C31115.92 (10)
C16—C15—H15120.2C28—C32—H32A108.3
C14—C15—H15120.2C31—C32—H32A108.3
C15—C16—C11121.38 (11)C28—C32—H32B108.3
C15—C16—H16119.3C31—C32—H32B108.3
C11—C16—H16119.3H32A—C32—H32B107.4
C6—C1—C2—C30.05 (16)C17—C11—C16—C15179.52 (10)
C7—C1—C2—C3179.81 (10)C16—C11—C17—O54.84 (17)
C1—C2—C3—C40.79 (17)C12—C11—C17—O5175.67 (11)
C8—O3—C4—C3179.71 (10)C16—C11—C17—O4175.24 (9)
C8—O3—C4—C50.69 (16)C12—C11—C17—O44.25 (16)
C2—C3—C4—O3179.73 (10)C14—O6—C18—C19178.58 (9)
C2—C3—C4—C51.21 (17)O6—C18—C19—C20179.25 (10)
O3—C4—C5—C6179.77 (10)C25—N1—C21—C220.98 (18)
C3—C4—C5—C60.78 (17)N1—C21—C22—C230.30 (19)
C4—C5—C6—C10.06 (17)C21—C22—C23—C240.73 (18)
C2—C1—C6—C50.48 (17)C21—C22—C23—C31179.59 (10)
C7—C1—C6—C5179.76 (10)C22—C23—C24—C251.05 (18)
C6—C1—C7—O28.98 (17)C31—C23—C24—C25179.28 (11)
C2—C1—C7—O2170.78 (11)C21—N1—C25—C240.6 (2)
C6—C1—C7—O1171.02 (10)C23—C24—C25—N10.4 (2)
C2—C1—C7—O19.22 (15)C30—N2—C26—C270.28 (18)
C4—O3—C8—C9179.75 (10)N2—C26—C27—C280.30 (19)
O3—C8—C9—C10176.05 (10)C26—C27—C28—C291.34 (17)
C16—C11—C12—C130.19 (17)C26—C27—C28—C32177.13 (10)
C17—C11—C12—C13179.68 (10)C27—C28—C29—C301.82 (17)
C11—C12—C13—C140.47 (17)C32—C28—C29—C30176.57 (10)
C18—O6—C14—C155.71 (16)C26—N2—C30—C290.25 (17)
C18—O6—C14—C13175.08 (10)C28—C29—C30—N21.35 (18)
C12—C13—C14—O6179.62 (10)C24—C23—C31—C323.71 (17)
C12—C13—C14—C150.37 (17)C22—C23—C31—C32176.64 (10)
O6—C14—C15—C16178.80 (10)C29—C28—C32—C3111.42 (17)
C13—C14—C15—C160.39 (17)C27—C28—C32—C31170.22 (10)
C14—C15—C16—C111.07 (18)C23—C31—C32—C28179.72 (9)
C12—C11—C16—C150.96 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.966 (18)1.657 (19)2.6207 (17)175.4 (16)
O4—H4···N21.010 (19)1.610 (19)2.6198 (17)179 (2)
C6—H6···O2i0.932.553.376 (2)149
C27—H27···O5ii0.932.523.389 (2)156
Symmetry codes: (i) x2, y, z+1; (ii) x+1, y+1, z+1.
(III) 4-n-Butoxybenzoic acid–1,2-bis(pyridin-4-yl)ethane (2/1) top
Crystal data top
2C11H14O3·C12H12N2Z = 2
Mr = 572.68F(000) = 612.00
Triclinic, P1Dx = 1.289 Mg m3
a = 7.702 (2) ÅMo Kα radiation, λ = 0.71075 Å
b = 10.726 (4) ÅCell parameters from 15221 reflections
c = 19.010 (7) Åθ = 3.0–30.2°
α = 83.861 (17)°µ = 0.09 mm1
β = 78.794 (16)°T = 93 K
γ = 73.612 (15)°Block, colorless
V = 1475.5 (9) Å30.40 × 0.20 × 0.10 mm
Data collection top
Rigaku R-AXIS RAPIDII
diffractometer
5219 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm-1Rint = 0.021
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 910
Tmin = 0.768, Tmax = 0.991k = 1213
14444 measured reflectionsl = 2424
6670 independent reflections
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)] = 0.043Hydrogen site location: mixed
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0705P)2 + 0.390P]
where P = (Fo2 + 2Fc2)/3
6670 reflections(Δ/σ)max = 0.001
389 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.36 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.

Refinement. Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.51653 (13)0.27771 (9)0.61192 (5)0.0218 (2)
O20.64354 (14)0.06698 (9)0.59129 (5)0.0236 (2)
O30.68036 (13)0.09242 (9)0.92200 (5)0.0209 (2)
O40.22564 (13)0.47777 (10)0.13269 (5)0.0230 (2)
O50.11681 (15)0.69204 (10)0.11701 (5)0.0309 (3)
O60.08262 (14)0.65267 (9)0.44591 (5)0.0225 (2)
N10.45623 (15)0.30647 (11)0.47936 (6)0.0192 (2)
N20.28494 (16)0.44868 (12)0.00061 (6)0.0218 (3)
C10.62039 (17)0.13761 (13)0.70801 (7)0.0163 (3)
C20.56165 (17)0.24210 (13)0.75274 (7)0.0182 (3)
H20.50500.32650.73430.022*
C30.58528 (18)0.22352 (13)0.82341 (7)0.0193 (3)
H30.54600.29530.85330.023*
C40.66680 (17)0.09943 (13)0.85130 (7)0.0178 (3)
C50.72677 (18)0.00590 (13)0.80742 (7)0.0182 (3)
H50.78300.09040.82600.022*
C60.70292 (17)0.01481 (13)0.73615 (7)0.0176 (3)
H60.74390.05650.70590.021*
C70.59569 (17)0.15588 (13)0.63141 (7)0.0171 (3)
C80.76407 (18)0.03082 (13)0.95543 (7)0.0191 (3)
H8A0.89370.06350.93210.023*
H8B0.69770.09570.95140.023*
C90.75313 (18)0.00767 (14)1.03313 (7)0.0201 (3)
H9A0.62240.02411.05540.024*
H9B0.81400.06121.03580.024*
C100.84284 (19)0.12942 (14)1.07582 (7)0.0234 (3)
H10A0.78230.19851.07330.028*
H10B0.97380.16111.05390.028*
C110.8294 (2)0.10349 (16)1.15397 (7)0.0275 (3)
H11A0.70000.07011.17550.041*
H11B0.89580.03901.15680.041*
H11C0.88360.18461.18000.041*
C120.13736 (17)0.61449 (13)0.23165 (7)0.0186 (3)
C130.14716 (18)0.50757 (13)0.26965 (7)0.0200 (3)
H130.16740.42320.24620.024*
C140.12777 (18)0.52337 (13)0.34095 (7)0.0206 (3)
H140.13310.45020.36620.025*
C150.10025 (17)0.64686 (13)0.37591 (7)0.0182 (3)
C160.09327 (18)0.75389 (13)0.33906 (7)0.0192 (3)
H160.07640.83790.36290.023*
C170.11117 (17)0.73674 (13)0.26720 (7)0.0189 (3)
H170.10540.80990.24180.023*
C180.15721 (18)0.60009 (14)0.15474 (7)0.0205 (3)
C190.02570 (19)0.77902 (13)0.48132 (7)0.0196 (3)
H19A0.12330.82460.48710.024*
H19B0.08710.83240.45280.024*
C200.01042 (18)0.75828 (13)0.55364 (7)0.0199 (3)
H20A0.09720.70360.54730.024*
H20B0.10590.71140.58310.024*
C210.0906 (2)0.88721 (14)0.59280 (7)0.0244 (3)
H21A0.21010.93170.56440.029*
H21B0.00700.94370.59640.029*
C220.1187 (2)0.86963 (16)0.66777 (8)0.0279 (3)
H22A0.00000.82880.69680.042*
H22B0.17230.95470.69030.042*
H22C0.20170.81410.66450.042*
C230.48692 (18)0.19855 (13)0.44432 (7)0.0200 (3)
H230.52830.11660.46880.024*
C240.46126 (18)0.20069 (13)0.37437 (7)0.0197 (3)
H240.48510.12140.35170.024*
C250.40048 (17)0.31899 (13)0.33696 (7)0.0176 (3)
C260.3688 (2)0.43079 (13)0.37340 (7)0.0224 (3)
H260.32790.51400.35020.027*
C270.3969 (2)0.42053 (14)0.44380 (7)0.0227 (3)
H270.37290.49820.46800.027*
C280.18349 (19)0.54309 (15)0.04192 (7)0.0249 (3)
H280.09360.61160.02300.030*
C290.20326 (19)0.54573 (14)0.11249 (7)0.0224 (3)
H290.12780.61510.14090.027*
C300.33331 (17)0.44704 (13)0.14174 (7)0.0176 (3)
C310.43955 (19)0.34872 (13)0.09681 (7)0.0213 (3)
H310.53100.27920.11410.026*
C320.41101 (19)0.35308 (14)0.02703 (7)0.0221 (3)
H320.48420.28510.00280.027*
C330.37029 (19)0.32021 (13)0.26098 (7)0.0203 (3)
H33A0.25470.29620.26220.024*
H33B0.47170.25250.23550.024*
C340.35958 (18)0.44973 (12)0.21788 (7)0.0174 (3)
H34A0.25620.51730.24250.021*
H34B0.47410.47490.21720.021*
H10.497 (3)0.288 (2)0.5597 (13)0.060 (7)*
H40.247 (3)0.468 (2)0.0805 (14)0.069 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0304 (5)0.0184 (5)0.0149 (5)0.0016 (4)0.0083 (4)0.0015 (4)
O20.0355 (6)0.0196 (5)0.0155 (5)0.0052 (4)0.0069 (4)0.0011 (4)
O30.0293 (5)0.0204 (5)0.0122 (5)0.0023 (4)0.0087 (4)0.0002 (4)
O40.0268 (5)0.0238 (5)0.0158 (5)0.0011 (4)0.0076 (4)0.0015 (4)
O50.0420 (6)0.0285 (6)0.0196 (5)0.0005 (5)0.0105 (4)0.0044 (4)
O60.0329 (5)0.0204 (5)0.0124 (5)0.0031 (4)0.0067 (4)0.0009 (4)
N10.0218 (6)0.0222 (6)0.0131 (5)0.0046 (5)0.0048 (4)0.0013 (4)
N20.0261 (6)0.0261 (6)0.0139 (5)0.0077 (5)0.0062 (4)0.0020 (4)
C10.0165 (6)0.0193 (6)0.0134 (6)0.0050 (5)0.0039 (4)0.0012 (5)
C20.0203 (6)0.0167 (6)0.0166 (6)0.0032 (5)0.0052 (5)0.0022 (5)
C30.0231 (7)0.0183 (6)0.0160 (6)0.0037 (5)0.0044 (5)0.0023 (5)
C40.0174 (6)0.0231 (7)0.0131 (6)0.0053 (5)0.0044 (4)0.0006 (5)
C50.0197 (6)0.0169 (6)0.0167 (6)0.0020 (5)0.0055 (5)0.0017 (5)
C60.0185 (6)0.0177 (6)0.0157 (6)0.0030 (5)0.0028 (5)0.0026 (5)
C70.0181 (6)0.0188 (6)0.0151 (6)0.0063 (5)0.0036 (4)0.0013 (5)
C80.0204 (6)0.0201 (7)0.0163 (6)0.0028 (5)0.0069 (5)0.0015 (5)
C90.0196 (6)0.0257 (7)0.0142 (6)0.0044 (5)0.0046 (5)0.0017 (5)
C100.0245 (7)0.0277 (7)0.0158 (7)0.0040 (6)0.0055 (5)0.0036 (5)
C110.0292 (8)0.0367 (8)0.0166 (7)0.0087 (6)0.0079 (5)0.0049 (6)
C120.0151 (6)0.0233 (7)0.0152 (6)0.0017 (5)0.0037 (5)0.0008 (5)
C130.0213 (7)0.0196 (6)0.0172 (6)0.0026 (5)0.0051 (5)0.0025 (5)
C140.0253 (7)0.0176 (6)0.0184 (7)0.0036 (5)0.0053 (5)0.0018 (5)
C150.0180 (6)0.0216 (7)0.0129 (6)0.0024 (5)0.0029 (4)0.0003 (5)
C160.0196 (6)0.0191 (6)0.0170 (6)0.0031 (5)0.0034 (5)0.0020 (5)
C170.0186 (6)0.0195 (6)0.0182 (6)0.0033 (5)0.0042 (5)0.0026 (5)
C180.0181 (6)0.0263 (7)0.0155 (6)0.0029 (5)0.0043 (5)0.0007 (5)
C190.0244 (7)0.0187 (6)0.0143 (6)0.0036 (5)0.0050 (5)0.0020 (5)
C200.0223 (7)0.0227 (7)0.0141 (6)0.0049 (5)0.0044 (5)0.0004 (5)
C210.0274 (7)0.0260 (7)0.0171 (7)0.0017 (6)0.0069 (5)0.0011 (5)
C220.0291 (8)0.0355 (8)0.0200 (7)0.0086 (6)0.0102 (6)0.0053 (6)
C230.0227 (7)0.0197 (6)0.0171 (6)0.0044 (5)0.0058 (5)0.0026 (5)
C240.0239 (7)0.0182 (6)0.0174 (6)0.0054 (5)0.0051 (5)0.0005 (5)
C250.0169 (6)0.0220 (7)0.0137 (6)0.0055 (5)0.0029 (4)0.0009 (5)
C260.0312 (7)0.0177 (6)0.0167 (7)0.0020 (6)0.0086 (5)0.0015 (5)
C270.0312 (7)0.0196 (7)0.0166 (7)0.0032 (6)0.0077 (5)0.0018 (5)
C280.0250 (7)0.0280 (7)0.0189 (7)0.0005 (6)0.0079 (5)0.0010 (5)
C290.0234 (7)0.0246 (7)0.0162 (6)0.0011 (6)0.0037 (5)0.0017 (5)
C300.0195 (6)0.0215 (6)0.0133 (6)0.0078 (5)0.0038 (5)0.0010 (5)
C310.0246 (7)0.0208 (7)0.0170 (7)0.0020 (5)0.0069 (5)0.0007 (5)
C320.0282 (7)0.0224 (7)0.0153 (6)0.0056 (6)0.0040 (5)0.0015 (5)
C330.0286 (7)0.0202 (7)0.0136 (6)0.0074 (5)0.0070 (5)0.0004 (5)
C340.0220 (6)0.0186 (6)0.0123 (6)0.0049 (5)0.0051 (5)0.0010 (5)
Geometric parameters (Å, º) top
O1—C71.3234 (16)C14—C151.3962 (19)
O1—H11.02 (2)C14—H140.9500
O2—C71.2144 (17)C15—C161.391 (2)
O3—C41.3606 (16)C16—C171.3871 (19)
O3—C81.4372 (16)C16—H160.9500
O4—C181.3240 (17)C17—H170.9500
O4—H41.03 (3)C19—C201.5053 (18)
O5—C181.2146 (18)C19—H19A0.9900
O6—C151.3568 (16)C19—H19B0.9900
O6—C191.4374 (16)C20—C211.5246 (19)
N1—C231.3374 (18)C20—H20A0.9900
N1—C271.3380 (18)C20—H20B0.9900
N2—C281.3314 (18)C21—C221.521 (2)
N2—C321.3384 (18)C21—H21A0.9900
C1—C61.3906 (18)C21—H21B0.9900
C1—C21.3971 (18)C22—H22A0.9800
C1—C71.4903 (18)C22—H22B0.9800
C2—C31.3764 (18)C22—H22C0.9800
C2—H20.9500C23—C241.3788 (19)
C3—C41.3977 (18)C23—H230.9500
C3—H30.9500C24—C251.3915 (18)
C4—C51.3939 (19)C24—H240.9500
C5—C61.3887 (18)C25—C261.3871 (19)
C5—H50.9500C25—C331.5051 (18)
C6—H60.9500C26—C271.3849 (19)
C8—C91.5062 (19)C26—H260.9500
C8—H8A0.9900C27—H270.9500
C8—H8B0.9900C28—C291.3833 (19)
C9—C101.5243 (19)C28—H280.9500
C9—H9A0.9900C29—C301.3875 (19)
C9—H9B0.9900C29—H290.9500
C10—C111.519 (2)C30—C311.3946 (19)
C10—H10A0.9900C30—C341.5044 (18)
C10—H10B0.9900C31—C321.3799 (19)
C11—H11A0.9800C31—H310.9500
C11—H11B0.9800C32—H320.9500
C11—H11C0.9800C33—C341.5251 (19)
C12—C171.3895 (19)C33—H33A0.9900
C12—C131.396 (2)C33—H33B0.9900
C12—C181.4865 (18)C34—H34A0.9900
C13—C141.3796 (19)C34—H34B0.9900
C13—H130.9500
C7—O1—H1112.6 (13)O5—C18—O4124.19 (13)
C4—O3—C8119.21 (10)O5—C18—C12122.87 (13)
C18—O4—H4113.1 (13)O4—C18—C12112.93 (12)
C15—O6—C19117.94 (10)O6—C19—C20107.13 (11)
C23—N1—C27117.21 (12)O6—C19—H19A110.3
C28—N2—C32117.67 (12)C20—C19—H19A110.3
C6—C1—C2118.85 (12)O6—C19—H19B110.3
C6—C1—C7119.97 (12)C20—C19—H19B110.3
C2—C1—C7121.18 (12)H19A—C19—H19B108.5
C3—C2—C1120.44 (12)C19—C20—C21111.41 (11)
C3—C2—H2119.8C19—C20—H20A109.3
C1—C2—H2119.8C21—C20—H20A109.3
C2—C3—C4120.22 (12)C19—C20—H20B109.3
C2—C3—H3119.9C21—C20—H20B109.3
C4—C3—H3119.9H20A—C20—H20B108.0
O3—C4—C5124.82 (12)C22—C21—C20112.54 (12)
O3—C4—C3115.04 (11)C22—C21—H21A109.1
C5—C4—C3120.13 (12)C20—C21—H21A109.1
C6—C5—C4118.85 (12)C22—C21—H21B109.1
C6—C5—H5120.6C20—C21—H21B109.1
C4—C5—H5120.6H21A—C21—H21B107.8
C5—C6—C1121.50 (12)C21—C22—H22A109.5
C5—C6—H6119.3C21—C22—H22B109.5
C1—C6—H6119.3H22A—C22—H22B109.5
O2—C7—O1123.76 (12)C21—C22—H22C109.5
O2—C7—C1122.85 (12)H22A—C22—H22C109.5
O1—C7—C1113.38 (11)H22B—C22—H22C109.5
O3—C8—C9106.52 (11)N1—C23—C24123.07 (12)
O3—C8—H8A110.4N1—C23—H23118.5
C9—C8—H8A110.4C24—C23—H23118.5
O3—C8—H8B110.4C23—C24—C25120.01 (12)
C9—C8—H8B110.4C23—C24—H24120.0
H8A—C8—H8B108.6C25—C24—H24120.0
C8—C9—C10112.97 (12)C26—C25—C24116.82 (12)
C8—C9—H9A109.0C26—C25—C33123.58 (12)
C10—C9—H9A109.0C24—C25—C33119.59 (12)
C8—C9—H9B109.0C27—C26—C25119.72 (13)
C10—C9—H9B109.0C27—C26—H26120.1
H9A—C9—H9B107.8C25—C26—H26120.1
C11—C10—C9111.88 (12)N1—C27—C26123.16 (13)
C11—C10—H10A109.2N1—C27—H27118.4
C9—C10—H10A109.2C26—C27—H27118.4
C11—C10—H10B109.2N2—C28—C29122.87 (13)
C9—C10—H10B109.2N2—C28—H28118.6
H10A—C10—H10B107.9C29—C28—H28118.6
C10—C11—H11A109.5C28—C29—C30119.95 (13)
C10—C11—H11B109.5C28—C29—H29120.0
H11A—C11—H11B109.5C30—C29—H29120.0
C10—C11—H11C109.5C29—C30—C31116.87 (12)
H11A—C11—H11C109.5C29—C30—C34120.72 (12)
H11B—C11—H11C109.5C31—C30—C34122.39 (12)
C17—C12—C13118.89 (12)C32—C31—C30119.61 (12)
C17—C12—C18119.51 (12)C32—C31—H31120.2
C13—C12—C18121.60 (12)C30—C31—H31120.2
C14—C13—C12120.56 (13)N2—C32—C31123.03 (13)
C14—C13—H13119.7N2—C32—H32118.5
C12—C13—H13119.7C31—C32—H32118.5
C13—C14—C15119.97 (13)C25—C33—C34115.09 (11)
C13—C14—H14120.0C25—C33—H33A108.5
C15—C14—H14120.0C34—C33—H33A108.5
O6—C15—C16124.24 (12)C25—C33—H33B108.5
O6—C15—C14115.68 (12)C34—C33—H33B108.5
C16—C15—C14120.08 (12)H33A—C33—H33B107.5
C17—C16—C15119.31 (12)C30—C34—C33113.82 (11)
C17—C16—H16120.3C30—C34—H34A108.8
C15—C16—H16120.3C33—C34—H34A108.8
C16—C17—C12121.17 (12)C30—C34—H34B108.8
C16—C17—H17119.4C33—C34—H34B108.8
C12—C17—H17119.4H34A—C34—H34B107.7
C6—C1—C2—C30.01 (19)C18—C12—C17—C16179.58 (11)
C7—C1—C2—C3179.91 (12)C17—C12—C18—O514.7 (2)
C1—C2—C3—C40.6 (2)C13—C12—C18—O5166.26 (14)
C8—O3—C4—C50.84 (19)C17—C12—C18—O4164.26 (12)
C8—O3—C4—C3179.33 (11)C13—C12—C18—O414.75 (18)
C2—C3—C4—O3179.01 (12)C15—O6—C19—C20171.63 (10)
C2—C3—C4—C50.8 (2)O6—C19—C20—C21174.20 (11)
O3—C4—C5—C6179.42 (12)C19—C20—C21—C22176.83 (12)
C3—C4—C5—C60.40 (19)C27—N1—C23—C240.4 (2)
C4—C5—C6—C10.23 (19)N1—C23—C24—C250.1 (2)
C2—C1—C6—C50.43 (19)C23—C24—C25—C260.1 (2)
C7—C1—C6—C5179.47 (12)C23—C24—C25—C33179.12 (12)
C6—C1—C7—O20.6 (2)C24—C25—C26—C270.4 (2)
C2—C1—C7—O2179.28 (13)C33—C25—C26—C27178.76 (13)
C6—C1—C7—O1179.56 (11)C23—N1—C27—C260.7 (2)
C2—C1—C7—O10.54 (17)C25—C26—C27—N10.8 (2)
C4—O3—C8—C9178.27 (11)C32—N2—C28—C290.1 (2)
O3—C8—C9—C10178.06 (11)N2—C28—C29—C300.0 (2)
C8—C9—C10—C11179.82 (12)C28—C29—C30—C310.2 (2)
C17—C12—C13—C141.19 (19)C28—C29—C30—C34178.69 (13)
C18—C12—C13—C14179.80 (12)C29—C30—C31—C320.4 (2)
C12—C13—C14—C150.8 (2)C34—C30—C31—C32178.80 (13)
C19—O6—C15—C169.84 (19)C28—N2—C32—C310.1 (2)
C19—O6—C15—C14170.46 (11)C30—C31—C32—N20.3 (2)
C13—C14—C15—O6179.97 (11)C26—C25—C33—C3418.14 (19)
C13—C14—C15—C160.3 (2)C24—C25—C33—C34162.70 (12)
O6—C15—C16—C17179.36 (12)C29—C30—C34—C33133.61 (14)
C14—C15—C16—C170.95 (19)C31—C30—C34—C3348.02 (17)
C15—C16—C17—C120.52 (19)C25—C33—C34—C30178.79 (10)
C13—C12—C17—C160.54 (19)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C6 and C12–C17 rings, respectively.
D—H···AD—HH···AD···AD—H···A
O1—H1···N11.02 (2)1.60 (2)2.6209 (18)177 (2)
O4—H4···N21.03 (3)1.58 (3)2.6092 (18)178.1 (19)
C32—H32···O3i0.952.573.524 (2)177
C11—H11A···Cg1ii0.982.803.662 (2)148
C33—H33A···Cg2iii0.992.743.598 (2)145
Symmetry codes: (i) x, y, z1; (ii) x+1, y, z+2; (iii) x, y+1, z.
 

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