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A low-temperature structural phase transition has been observed for form (II) of benzocaine (BZC). Lowering the temperature doubles the b-axis repeat and changes the space group from P212121 to P1121 with γ now 99.37 °. The structure is twinned, the twin rule corresponding to a 21 screw rotation parallel to a. The phase transition is associated with a sequential displacement parallel to a of zigzag bi-layers of ribbons perpendicular to b*. No similar phase transition was observed for form (I) and this was attributed to the different packing symmetries of the two room-temperature polymorphic forms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768109018898/so5027sup1.cif
Contains datablocks global, III, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768109018898/so5027Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768109018898/so5027IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768109018898/so5027IIIsup4.hkl
Contains datablock III

CCDC references: 746160; 746161; 746162

Computing details top

For all compounds, data collection: Collect (Nonius BV, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: DENZO and Scalepak (Otwinowski & Minor, 1997). Program(s) used to solve structure: known for (I), (II); Packing arguments for (III). Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for (I), (II); RAELS2006 (Rae, 2006) for (III). For all compounds, molecular graphics: Xtal3.7 (Hall et al., 2001); software used to prepare material for publication: Xtal3.7 (Hall et al., 2001).

(I) ethyl 4-aminobenzoate top
Crystal data top
C9H11NO2F(000) = 352
Mr = 165.19Dx = 1.211 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 83119 reflections
a = 8.2570 (7) Åθ = 2.6–25.0°
b = 5.5009 (4) ŵ = 0.09 mm1
c = 19.956 (2) ÅT = 300 K
β = 91.699 (4)°Block, colourless
V = 906.02 (14) Å30.15 × 0.15 × 0.07 mm
Z = 4
Data collection top
KappaCCD
diffractometer
1595 independent reflections
Radiation source: fine-focus sealed tube1108 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 9 pixels mm-1θmax = 25.1°, θmin = 3.2°
CCD scansh = 99
Absorption correction: integration
Gaussian integration (Coppens, 1970)
k = 66
Tmin = 0.980, Tmax = 0.989l = 2323
12216 measured 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: inferred from neighbouring sites
wR(F2) = 0.122All H-atom parameters refined
S = 1.01 w = 1/[σ2(Fo2) + (0.0631P)2 + 0.1023P]
where P = (Fo2 + 2Fc2)/3
1595 reflections(Δ/σ)max < 0.001
153 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = 0.10 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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.47994 (18)0.4098 (3)0.35998 (7)0.0602 (4)
C20.3381 (2)0.5278 (3)0.37717 (9)0.0683 (5)
C30.1889 (2)0.4420 (3)0.35654 (9)0.0700 (5)
C40.17547 (19)0.2330 (3)0.31754 (7)0.0621 (4)
C50.3176 (2)0.1155 (3)0.29952 (8)0.0661 (5)
C60.4662 (2)0.2028 (3)0.32038 (8)0.0656 (5)
C70.6407 (2)0.4978 (3)0.38208 (8)0.0672 (5)
O80.76791 (14)0.4103 (2)0.36567 (6)0.0895 (5)
O90.63403 (13)0.6869 (2)0.42404 (6)0.0802 (4)
C100.7866 (2)0.7865 (5)0.44921 (13)0.0903 (6)
C110.7475 (3)0.9811 (5)0.49787 (13)0.0931 (7)
N120.0263 (2)0.1503 (3)0.29546 (9)0.0831 (5)
H130.347 (2)0.668 (3)0.4029 (8)0.081 (5)*
H140.092 (2)0.523 (3)0.3709 (8)0.078 (5)*
H150.3051 (19)0.030 (3)0.2739 (8)0.074 (5)*
H160.562 (2)0.124 (3)0.3068 (7)0.069 (4)*
H170.842 (3)0.838 (4)0.4110 (10)0.107 (7)*
H180.846 (3)0.641 (4)0.4707 (10)0.112 (7)*
H190.680 (3)1.102 (5)0.4772 (13)0.138 (10)*
H200.848 (3)1.059 (4)0.5160 (11)0.122 (7)*
H210.688 (3)0.919 (4)0.5369 (13)0.137 (9)*
H220.058 (3)0.208 (4)0.3146 (10)0.092 (6)*
H230.023 (2)0.001 (4)0.2767 (10)0.096 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0603 (9)0.0598 (9)0.0607 (9)0.0027 (7)0.0036 (7)0.0017 (7)
C20.0676 (11)0.0617 (10)0.0753 (11)0.0047 (8)0.0004 (8)0.0102 (9)
C30.0599 (10)0.0685 (11)0.0814 (11)0.0103 (8)0.0010 (8)0.0107 (9)
C40.0618 (10)0.0613 (9)0.0632 (9)0.0010 (7)0.0017 (7)0.0006 (8)
C50.0728 (11)0.0590 (10)0.0668 (10)0.0027 (8)0.0047 (8)0.0078 (8)
C60.0620 (10)0.0668 (10)0.0686 (10)0.0078 (8)0.0086 (8)0.0017 (8)
C70.0635 (10)0.0715 (11)0.0666 (10)0.0020 (8)0.0040 (8)0.0037 (8)
O80.0610 (8)0.1057 (10)0.1022 (10)0.0041 (6)0.0089 (6)0.0169 (8)
O90.0646 (7)0.0837 (8)0.0921 (9)0.0049 (6)0.0014 (6)0.0180 (7)
C100.0693 (12)0.1033 (16)0.0981 (15)0.0173 (11)0.0007 (11)0.0148 (14)
C110.0922 (15)0.0925 (15)0.0937 (16)0.0157 (13)0.0098 (13)0.0112 (13)
N120.0660 (10)0.0829 (12)0.1000 (12)0.0003 (8)0.0013 (8)0.0226 (9)
Geometric parameters (Å, º) top
C1—C61.389 (2)C7—O81.2097 (18)
C1—C21.391 (2)C7—O91.3373 (19)
C1—C71.468 (2)O9—C101.450 (2)
C2—C31.371 (2)C10—C111.487 (3)
C2—H130.927 (17)C10—H170.94 (2)
C3—C41.391 (2)C10—H181.02 (2)
C3—H140.965 (17)C11—H190.95 (3)
C4—N121.373 (2)C11—H200.99 (3)
C4—C51.397 (2)C11—H210.99 (3)
C5—C61.370 (2)N12—H220.86 (2)
C5—H150.954 (17)N12—H230.91 (2)
C6—H160.951 (16)
C6—C1—C2117.87 (15)O8—C7—C1124.91 (16)
C6—C1—C7119.95 (14)O9—C7—C1113.02 (14)
C2—C1—C7122.18 (15)C7—O9—C10117.35 (14)
C3—C2—C1121.40 (16)O9—C10—C11107.14 (18)
C3—C2—H13120.5 (11)O9—C10—H17105.6 (13)
C1—C2—H13118.1 (11)C11—C10—H17115.6 (13)
C2—C3—C4120.58 (16)O9—C10—H18104.3 (12)
C2—C3—H14119.7 (10)C11—C10—H18113.4 (12)
C4—C3—H14119.6 (10)H17—C10—H18109.7 (19)
N12—C4—C3120.63 (15)C10—C11—H19110.8 (15)
N12—C4—C5121.10 (16)C10—C11—H20110.6 (13)
C3—C4—C5118.23 (15)H19—C11—H20109 (2)
C6—C5—C4120.73 (16)C10—C11—H21112.8 (14)
C6—C5—H15122.6 (10)H19—C11—H21106 (2)
C4—C5—H15116.6 (10)H20—C11—H21106.9 (19)
C5—C6—C1121.18 (15)C4—N12—H22117.3 (13)
C5—C6—H16120.1 (10)C4—N12—H23116.8 (12)
C1—C6—H16118.7 (10)H22—N12—H23120.3 (18)
O8—C7—O9122.07 (15)
C6—C1—C2—C30.8 (3)C7—C1—C6—C5179.44 (15)
C7—C1—C2—C3179.47 (15)C6—C1—C7—O84.0 (3)
C1—C2—C3—C40.0 (3)C2—C1—C7—O8175.79 (16)
C2—C3—C4—N12178.38 (16)C6—C1—C7—O9175.04 (14)
C2—C3—C4—C50.7 (3)C2—C1—C7—O95.2 (2)
N12—C4—C5—C6178.35 (15)O8—C7—O9—C100.5 (3)
C3—C4—C5—C60.7 (2)C1—C7—O9—C10179.58 (17)
C4—C5—C6—C10.1 (3)C7—O9—C10—C11176.18 (18)
C2—C1—C6—C50.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N12—H22···O8i0.86 (2)2.11 (2)2.956 (2)168.5 (18)
N12—H23···N12ii0.91 (2)2.43 (2)3.3165 (19)165.3 (16)
Symmetry codes: (i) x1, y, z; (ii) x, y1/2, z+1/2.
(II) ethyl 4-aminobenzoate top
Crystal data top
C9H11NO2F(000) = 352
Mr = 165.19Dx = 1.199 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P_2n_2aCell parameters from 87498 reflections
a = 8.2424 (4) Åθ = 2.6–27.5°
b = 5.3111 (3) ŵ = 0.09 mm1
c = 20.9044 (12) ÅT = 300 K
V = 915.12 (9) Å3Block, colourless
Z = 40.28 × 0.24 × 0.17 mm
Data collection top
KappaCCD
diffractometer
1241 independent reflections
Radiation source: fine-focus sealed tube1003 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 2.7°
CCD scansh = 1010
Absorption correction: integration
Gaussian integration (Coppens, 1970)
k = 66
Tmin = 0.958, Tmax = 0.978l = 2727
20874 measured 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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0568P)2 + 0.047P]
where P = (Fo2 + 2Fc2)/3
1241 reflections(Δ/σ)max < 0.001
117 parametersΔρmax = 0.08 e Å3
0 restraintsΔρmin = 0.08 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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4689 (2)0.4008 (4)0.35899 (8)0.0695 (5)
C60.4584 (3)0.1916 (4)0.31889 (9)0.0752 (5)
H160.55280.10990.30610.090*
C50.3117 (3)0.1047 (4)0.29808 (9)0.0754 (5)
H150.30790.03470.27120.091*
C40.1678 (3)0.2212 (4)0.31642 (9)0.0717 (5)
C30.1778 (3)0.4337 (4)0.35550 (10)0.0799 (5)
H140.08370.51780.36750.096*
C20.3256 (3)0.5191 (4)0.37624 (9)0.0782 (5)
H130.32980.66010.40260.094*
C70.6287 (3)0.4890 (4)0.38049 (9)0.0768 (5)
O80.75711 (19)0.4041 (4)0.36279 (8)0.1012 (6)
O90.61964 (19)0.6744 (3)0.42355 (7)0.0905 (5)
C100.7728 (3)0.7766 (6)0.44661 (13)0.1036 (8)
H170.83110.84650.41280.124*
H180.83530.6490.46490.124*
C110.7352 (4)0.9723 (7)0.49486 (13)0.1154 (9)
H190.66341.09490.47650.173*
H200.83381.05320.50810.173*
H210.68410.89550.53120.173*
N120.0191 (2)0.1378 (4)0.29485 (10)0.0898 (6)
H230.017 (3)0.035 (5)0.2773 (11)0.108*
H220.074 (3)0.199 (5)0.3138 (12)0.108*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0782 (12)0.0682 (11)0.0620 (9)0.0017 (10)0.0028 (9)0.0014 (9)
C60.0805 (12)0.0684 (11)0.0767 (10)0.0058 (11)0.0076 (10)0.0054 (10)
C50.0880 (13)0.0649 (11)0.0734 (10)0.0029 (11)0.0039 (10)0.0100 (9)
C40.0833 (12)0.0658 (10)0.0661 (9)0.0023 (10)0.0016 (9)0.0016 (9)
C30.0799 (12)0.0742 (12)0.0856 (12)0.0122 (12)0.0014 (10)0.0126 (10)
C20.0872 (12)0.0695 (11)0.0779 (11)0.0064 (12)0.0003 (10)0.0141 (10)
C70.0832 (12)0.0786 (13)0.0686 (10)0.0007 (11)0.0006 (10)0.0007 (10)
O80.0782 (9)0.1189 (14)0.1065 (12)0.0008 (10)0.0062 (8)0.0239 (11)
O90.0901 (10)0.0908 (10)0.0905 (9)0.0025 (9)0.0085 (8)0.0189 (9)
C100.0949 (17)0.111 (2)0.1043 (16)0.0133 (16)0.0134 (13)0.0155 (17)
C110.132 (2)0.107 (2)0.1069 (17)0.0092 (18)0.0227 (16)0.0195 (16)
N120.0825 (12)0.0827 (13)0.1041 (14)0.0012 (11)0.0036 (10)0.0173 (11)
Geometric parameters (Å, º) top
C1—C21.386 (3)C7—O81.209 (3)
C1—C61.395 (3)C7—O91.336 (2)
C1—C71.468 (3)O9—C101.457 (3)
C6—C51.365 (3)C10—C111.481 (4)
C6—H160.9300C10—H170.9320
C5—C41.392 (3)C10—H180.9320
C5—H150.9300C11—H190.9600
C4—N121.379 (3)C11—H200.9600
C4—C31.396 (3)C11—H210.9600
C3—C21.370 (3)N12—H230.99 (3)
C3—H140.9300N12—H220.92 (2)
C2—H130.9300
C2—C1—C6117.67 (18)O8—C7—C1124.93 (19)
C2—C1—C7122.71 (18)O9—C7—C1113.04 (19)
C6—C1—C7119.62 (18)C7—O9—C10116.69 (19)
C5—C6—C1121.07 (19)O9—C10—C11107.8 (2)
C5—C6—H16119.5O9—C10—H17110.2
C1—C6—H16119.5C11—C10—H17110.2
C6—C5—C4121.10 (18)O9—C10—H18110.2
C6—C5—H15119.4C11—C10—H18110.2
C4—C5—H15119.4H17—C10—H18108.5
N12—C4—C5121.63 (18)C10—C11—H19109.5
N12—C4—C3120.27 (19)C10—C11—H20109.5
C5—C4—C3118.05 (18)H19—C11—H20109.5
C2—C3—C4120.36 (19)C10—C11—H21109.5
C2—C3—H14119.8H19—C11—H21109.5
C4—C3—H14119.8H20—C11—H21109.5
C3—C2—C1121.71 (18)C4—N12—H23115.6 (16)
C3—C2—H13119.1C4—N12—H22119.1 (16)
C1—C2—H13119.1H23—N12—H22118 (2)
O8—C7—O9122.0 (2)
C2—C1—C6—C50.8 (3)C7—C1—C2—C3179.9 (2)
C7—C1—C6—C5179.9 (2)C2—C1—C7—O8174.0 (2)
C1—C6—C5—C40.3 (3)C6—C1—C7—O85.2 (3)
C6—C5—C4—N12178.9 (2)C2—C1—C7—O97.1 (3)
C6—C5—C4—C31.5 (3)C6—C1—C7—O9173.69 (16)
N12—C4—C3—C2179.1 (2)O8—C7—O9—C102.2 (3)
C5—C4—C3—C21.7 (3)C1—C7—O9—C10178.9 (2)
C4—C3—C2—C10.6 (3)C7—O9—C10—C11178.3 (2)
C6—C1—C2—C30.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N12—H22···O8i0.92 (2)2.04 (3)2.946 (3)166 (2)
N12—H23···N12ii0.99 (3)2.32 (3)3.266 (2)160 (2)
Symmetry codes: (i) x1, y, z; (ii) x, y1/2, z+1/2.
(III) ethyl 4-aminobenzoate top
Crystal data top
C9H11NO2F(000) = 704
Mr = 165.19Dx = 1.247 Mg m3
Monoclinic, P1121Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2cCell parameters from 156810 reflections
a = 8.1883 (4) Åθ = 2.6–27.5°
b = 10.6394 (5) ŵ = 0.09 mm1
c = 20.4761 (10) ÅT = 300 K
β = 90°Block, colourless
V = 1760.05 (15) Å30.28 × 0.24 × 0.17 mm
Z = 8
Data collection top
KappaCCD
diffractometer
7859 independent reflections
Radiation source: fine-focus sealed tube6013 reflections with I > 3 σ(I)
Graphite monochromatorRint = 0.063
Detector resolution: 9 pixels mm-1θmax = 27.6°, θmin = 2.7°
CCD scansh = 1010
Absorption correction: integration
Gaussian integration (Coppens, 1970)
k = 1313
Tmin = 0.952, Tmax = 0.974l = 2626
24960 measured reflections
Refinement top
Refinement on FPrimary atom site location: packing arguments
Least-squares matrix: fullSecondary atom site location: packing arguments
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 2.10 w = 1/[σ2(F) + (0.03F)2]
6013 reflections(Δ/σ)max = 0.01
143 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = 0.11 e Å3
Special details top

Experimental. The twinning in Form III was ignored in the data processing, reflection intensities being obtained using only reflection positions h for the major twin component.

Refinement. The final twin ratio was 0.523 (2):0.477. The twinning was included in the model for observed intensities as Ycalc(h) = a I(h) + (1 - a) K(|h-h'|) I(h') where K(|h-h'|) is an empirical function allowing for overlap with the nearest twin related reflection h'. K(|h-h'|) is 0.5 if p = |h-h'| is equal to a refinable parameter p1, 1.0 if less than a refinable parameter p2, 0.0 if greater than 2 p1 - p2 and 0.5 - 0.5 sin[Pi (p - p1)/2(p1 - p2)] for p in the range p2 to 2 p1 - p2. The nearest twin related reflection to h,k,l has h' = h, l' = - l and k' the nearest integer to -k -0.42309 h. Final parameter values were p1 = 0.139 (3) b* and p2 = 0.0. To demonstrate the adequacy of the twin overlap model the reflection data considered observed were separated into 8 sets, corresponding to p = 0, 0 < p/b* = 0.1, 0.1 < p/b* = 0.2 and p/b* > 0.2 for k even (1 to 4) and k odd (5 to 8) respectively. For the 216, 299, 845, 1578, 210, 299, 869, 1697 reflections in each set the final values for R(F) were 0.063, 0.041, 0.082, 0.072, 0.059, 0.042, 0.080, 0.057. Rigid body TLX parameterization was used to describe and refine the atomic displacement parameters of every atom in a molecule.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C110.5566 (2)0.32209 (15)0.36344 (6)0.0272 (4)
C120.5277 (2)0.21927 (19)0.32048 (9)0.0311 (4)
C130.3693 (2)0.17263 (17)0.29933 (9)0.0304 (4)
C140.2346 (2)0.22807 (15)0.32077 (8)0.0287 (4)
C150.2645 (2)0.33153 (18)0.36400 (10)0.0304 (4)
C160.4233 (2)0.37753 (17)0.38490 (9)0.0283 (4)
C170.7276 (3)0.3689 (2)0.38480 (10)0.0312 (4)
O180.8487 (3)0.3239 (3)0.36865 (13)0.0401 (5)
O190.7374 (3)0.4651 (2)0.42774 (12)0.0325 (4)
C1100.9029 (4)0.5163 (4)0.45196 (19)0.0394 (6)
C1110.8810 (5)0.6131 (4)0.5028 (2)0.0470 (11)
N1120.0767 (2)0.1822 (2)0.29996 (11)0.0337 (4)
C210.7047 (2)0.56163 (15)0.13936 (7)0.0285 (4)
C220.6906 (2)0.45818 (19)0.18190 (9)0.0313 (4)
C230.8298 (2)0.41356 (17)0.20404 (9)0.0298 (5)
C240.9880 (2)0.47171 (15)0.18405 (8)0.0291 (5)
C251.0015 (2)0.57579 (18)0.14123 (10)0.0309 (5)
C260.8616 (2)0.61977 (17)0.11934 (9)0.0287 (5)
C270.5530 (3)0.6062 (2)0.11691 (10)0.0329 (4)
O280.4131 (3)0.5538 (2)0.13033 (14)0.0420 (7)
O290.5813 (3)0.7059 (2)0.07689 (12)0.0328 (4)
C2100.4357 (4)0.7532 (4)0.0525 (2)0.0395 (6)
C2110.4938 (5)0.8655 (4)0.0093 (2)0.0425 (9)
N2121.1271 (2)0.4279 (2)0.20586 (11)0.0336 (6)
C310.7033 (2)0.81687 (16)0.35695 (6)0.0281 (5)
C320.6712 (2)0.70534 (19)0.32019 (9)0.0308 (5)
C330.5130 (2)0.65943 (17)0.29862 (9)0.0301 (5)
C340.3817 (2)0.72441 (15)0.31339 (8)0.0301 (4)
C350.4146 (2)0.83662 (18)0.35040 (10)0.0338 (4)
C360.5733 (2)0.88181 (17)0.37176 (9)0.0310 (4)
C370.8740 (3)0.8625 (2)0.37898 (10)0.0310 (5)
O380.9935 (3)0.8136 (2)0.36615 (13)0.0386 (6)
O390.8832 (3)0.9591 (2)0.42229 (12)0.0324 (4)
C3101.0443 (4)1.0066 (3)0.44995 (18)0.0371 (5)
C3111.0274 (5)1.1221 (4)0.4900 (2)0.0448 (6)
N3120.2239 (2)0.6794 (2)0.29212 (11)0.0346 (5)
C410.8234 (2)0.06483 (16)0.14551 (6)0.0303 (4)
C420.8084 (2)0.04434 (19)0.18410 (9)0.0332 (4)
C430.9458 (2)0.09817 (17)0.19974 (9)0.0323 (4)
C441.1031 (2)0.04379 (16)0.17699 (8)0.0320 (4)
C451.1175 (2)0.06608 (19)0.13816 (10)0.0344 (5)
C460.9794 (2)0.11926 (18)0.12278 (9)0.0318 (5)
C470.6736 (3)0.1192 (2)0.12998 (11)0.0341 (4)
O480.5359 (3)0.0809 (3)0.15084 (14)0.0427 (5)
O490.6984 (3)0.1995 (2)0.07735 (12)0.0351 (5)
C4100.5552 (5)0.2492 (4)0.0535 (2)0.0414 (7)
C4110.6131 (5)0.3457 (4)0.0019 (2)0.0474 (9)
N4121.2404 (2)0.0968 (2)0.19233 (12)0.0370 (5)
H1C120.622560.178860.304820.040
H1C130.350370.098790.268500.037
H1C150.170030.372280.379820.039
H1C160.442880.451350.415720.033
H1C1100.973650.557270.415520.045
H2C1100.955580.446700.471580.042
H1C1110.991520.651030.520880.053
H2C1110.827440.681830.482710.052
H3C1110.809370.571260.538770.049
H1N1120.056550.108430.269130.036
H2N1120.018160.222670.315630.040
H1C220.578530.415850.196540.039
H1C230.817760.339230.234560.034
H1C251.113280.618460.126440.038
H1C260.872970.694060.088820.032
H1C2100.370640.779850.089910.046
H2C2100.364860.684990.026960.042
H1C2110.395920.899920.008160.048
H2C2110.565010.933130.035090.046
H3C2110.559240.838280.027870.042
H1N2121.116320.353620.236380.034
H2N2121.239140.470240.191210.040
H1C320.763740.658080.309320.038
H1C330.491810.579270.272290.035
H1C350.322580.884230.361400.044
H1C360.595130.961930.398110.037
H1C3101.126861.030340.414230.039
H2C3101.081170.939980.478270.041
H1C3111.136871.157420.509890.049
H2C3110.989941.188050.461400.048
H3C3110.944241.097690.525450.050
H1N3120.201490.599290.265760.035
H2N3120.131410.726650.303000.042
H1C420.696970.084070.200640.041
H1C430.933130.176520.227480.037
H1C451.228630.106190.121500.043
H1C460.991390.197600.095050.036
H1C4100.502380.290260.090090.044
H2C4100.473210.178610.034610.047
H1C4110.516520.381780.015530.053
H2C4110.695420.415680.021100.049
H3C4110.666250.304020.034390.052
H1N4121.228960.175100.220040.038
H2N4121.351770.057000.175780.044
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0267 (5)0.0276 (6)0.0272 (7)0.0047 (4)0.0003 (4)0.0009 (5)
C120.0285 (4)0.0320 (6)0.0333 (7)0.0070 (4)0.0009 (5)0.0062 (5)
C130.0296 (5)0.0297 (7)0.0322 (7)0.0055 (4)0.0015 (5)0.0048 (6)
C140.0273 (5)0.0295 (6)0.0289 (6)0.0038 (4)0.0003 (4)0.0013 (5)
C150.0271 (5)0.0328 (6)0.0318 (6)0.0062 (4)0.0001 (5)0.0047 (5)
C160.0277 (4)0.0286 (7)0.0289 (7)0.0054 (4)0.0001 (4)0.0028 (5)
C170.0271 (4)0.0341 (6)0.0323 (6)0.0045 (4)0.0008 (4)0.0033 (4)
O180.0274 (5)0.0485 (11)0.0451 (12)0.0081 (4)0.0025 (5)0.0124 (8)
O190.0299 (5)0.0333 (7)0.0334 (7)0.0027 (4)0.0025 (4)0.0037 (5)
C1100.0320 (5)0.0426 (10)0.0417 (10)0.0006 (6)0.0055 (6)0.0068 (8)
C1110.0403 (10)0.0479 (15)0.0507 (15)0.0009 (9)0.0101 (10)0.0157 (12)
N1120.0282 (5)0.0371 (6)0.0350 (7)0.0027 (4)0.0019 (5)0.0039 (6)
C210.0253 (6)0.0294 (6)0.0297 (6)0.0016 (4)0.0010 (5)0.0005 (5)
C220.0258 (7)0.0334 (6)0.0335 (6)0.0011 (5)0.0023 (5)0.0046 (6)
C230.0273 (6)0.0302 (7)0.0307 (7)0.0012 (5)0.0009 (5)0.0023 (6)
C240.0259 (5)0.0295 (6)0.0308 (6)0.0013 (4)0.0005 (5)0.0004 (5)
C250.0250 (5)0.0313 (5)0.0348 (8)0.0003 (5)0.0000 (6)0.0032 (5)
C260.0259 (5)0.0280 (6)0.0308 (7)0.0001 (4)0.0001 (5)0.0010 (5)
C270.0266 (6)0.0360 (5)0.0358 (6)0.0042 (4)0.0009 (4)0.0032 (5)
O280.0258 (8)0.0496 (11)0.0503 (12)0.0051 (6)0.0023 (4)0.0127 (9)
O290.0306 (6)0.0331 (6)0.0348 (7)0.0052 (4)0.0016 (5)0.0012 (5)
C2100.0348 (8)0.0417 (8)0.0432 (11)0.0102 (7)0.0035 (7)0.0038 (7)
C2110.0441 (12)0.0394 (10)0.0456 (15)0.0111 (9)0.0071 (10)0.0048 (9)
N2120.0278 (5)0.0352 (6)0.0373 (7)0.0034 (5)0.0021 (6)0.0027 (5)
C310.0289 (5)0.0281 (7)0.0271 (8)0.0042 (4)0.0014 (5)0.0002 (5)
C320.0295 (5)0.0311 (7)0.0319 (8)0.0051 (5)0.0015 (5)0.0042 (5)
C330.0304 (5)0.0302 (7)0.0293 (7)0.0041 (4)0.0010 (5)0.0028 (5)
C340.0296 (5)0.0297 (6)0.0308 (7)0.0045 (4)0.0005 (5)0.0007 (5)
C350.0301 (5)0.0314 (7)0.0403 (10)0.0068 (4)0.0016 (5)0.0053 (7)
C360.0303 (5)0.0290 (7)0.0340 (9)0.0056 (4)0.0002 (5)0.0033 (6)
C370.0293 (5)0.0314 (7)0.0318 (7)0.0038 (4)0.0004 (5)0.0016 (4)
O380.0290 (6)0.0398 (11)0.0469 (12)0.0057 (5)0.0008 (5)0.0089 (7)
O390.0321 (5)0.0318 (6)0.0325 (7)0.0026 (4)0.0011 (5)0.0024 (5)
C3100.0344 (6)0.0370 (8)0.0384 (10)0.0009 (5)0.0041 (6)0.0033 (7)
C3110.0413 (10)0.0431 (11)0.0476 (16)0.0005 (8)0.0058 (10)0.0124 (11)
N3120.0307 (5)0.0341 (7)0.0387 (9)0.0043 (4)0.0032 (6)0.0024 (6)
C410.0317 (6)0.0299 (6)0.0278 (8)0.0005 (4)0.0000 (5)0.0005 (5)
C420.0322 (6)0.0327 (6)0.0329 (8)0.0004 (4)0.0013 (5)0.0034 (6)
C430.0335 (5)0.0310 (6)0.0307 (9)0.0006 (4)0.0002 (5)0.0017 (6)
C440.0324 (6)0.0315 (5)0.0308 (7)0.0014 (4)0.0004 (5)0.0002 (5)
C450.0318 (6)0.0345 (5)0.0355 (7)0.0010 (4)0.0017 (5)0.0042 (5)
C460.0323 (5)0.0312 (6)0.0303 (8)0.0003 (4)0.0007 (5)0.0018 (5)
C470.0327 (5)0.0338 (5)0.0348 (7)0.0022 (4)0.0004 (4)0.0016 (5)
O480.0328 (6)0.0441 (11)0.0506 (12)0.0046 (5)0.0029 (5)0.0099 (8)
O490.0365 (6)0.0337 (6)0.0342 (8)0.0028 (4)0.0033 (5)0.0014 (5)
C4100.0402 (8)0.0387 (9)0.0448 (11)0.0054 (7)0.0074 (7)0.0034 (8)
C4110.0504 (14)0.0451 (14)0.0472 (16)0.0090 (11)0.0081 (11)0.0094 (11)
N4120.0342 (6)0.0364 (6)0.0398 (8)0.0038 (5)0.0013 (5)0.0026 (5)
H1C120.0310.0440.0460.0110.0030.017
H1C130.0340.0360.0420.0070.0040.012
H1C150.0290.0450.0440.0100.0020.014
H1C160.0310.0340.0360.0070.0020.009
H1C1100.0330.0490.0470.0050.0040.005
H2C1100.0330.0490.0450.0050.0090.008
H1C1110.0430.0550.0580.0020.0130.018
H2C1110.0470.0420.0650.0010.0140.018
H3C1110.0420.0590.0440.0030.0090.019
H1N1120.0310.0370.0380.0010.0040.005
H2N1120.0270.0480.0430.0050.0020.010
H1C220.0270.0440.0450.0010.0040.013
H1C230.0310.0340.0360.0020.0010.007
H1C250.0250.0400.0470.0010.0000.011
H1C260.0280.0300.0360.0000.0000.004
H1C2100.0400.0530.0480.0190.0000.005
H2C2100.0330.0450.0490.0070.0080.006
H1C2110.0490.0460.0520.0160.0100.006
H2C2110.0510.0360.0510.0120.0100.004
H3C2110.0450.0410.0420.0090.0060.008
H1N2120.0320.0350.0370.0050.0030.002
H2N2120.0270.0440.0490.0040.0020.009
H1C320.0310.0380.0470.0070.0000.013
H1C330.0330.0350.0370.0040.0000.009
H1C350.0320.0390.0610.0100.0050.015
H1C360.0330.0320.0450.0070.0020.010
H1C3100.0330.0400.0430.0010.0020.003
H2C3100.0380.0420.0420.0010.0100.001
H1C3110.0440.0480.0520.0030.0090.013
H2C3110.0440.0370.0610.0010.0090.013
H3C3110.0450.0560.0460.0020.0030.020
H1N3120.0330.0350.0360.0020.0030.002
H2N3120.0310.0400.0560.0070.0060.008
H1C420.0330.0410.0470.0010.0040.012
H1C430.0370.0340.0380.0010.0000.007
H1C450.0320.0440.0510.0020.0050.014
H1C460.0350.0350.0380.0010.0010.007
H1C4100.0400.0420.0510.0090.0040.004
H2C4100.0430.0420.0540.0050.0150.003
H1C4110.0550.0490.0560.0120.0130.011
H2C4110.0490.0410.0550.0060.0060.013
H3C4110.0610.0560.0420.0150.0070.012
H1N4120.0370.0360.0400.0050.0040.002
H2N4120.0340.0450.0540.0060.0010.009
Geometric parameters (Å, º) top
C11—C121.394 (1)O49—C4101.447 (4)
C11—C161.394 (1)C410—C4111.496 (5)
C11—C171.474 (2)C12—H1C121.000
C12—C131.381 (2)C13—H1C131.000
C13—C141.403 (1)C15—H1C151.000
C14—C151.403 (1)C16—H1C161.000
C14—N1121.373 (2)C110—H1C1101.000
C15—C161.381 (2)C110—H2C1101.000
C17—O181.215 (3)C111—H1C1111.000
C17—O191.342 (3)C111—H2C1111.000
O19—C1101.463 (4)C111—H3C1111.000
C110—C1111.495 (6)N112—H1N1121.000
C21—C221.394 (1)N112—H2N1121.000
C21—C261.394 (1)C22—H1C221.000
C21—C271.474 (2)C23—H1C231.000
C22—C231.381 (2)C25—H1C251.000
C23—C241.403 (1)C26—H1C261.000
C24—C251.403 (1)C210—H1C2101.000
C24—N2121.373 (2)C210—H2C2101.000
C25—C261.381 (2)C211—H1C2111.000
C27—O281.221 (3)C211—H2C2111.000
C27—O291.330 (3)C211—H3C2111.000
O29—C2101.455 (4)N212—H1N2121.000
C210—C2111.501 (5)N212—H2N2121.000
C31—C321.394 (1)C32—H1C321.000
C31—C361.394 (1)C33—H1C331.000
C31—C371.474 (2)C35—H1C351.000
C32—C331.381 (2)C36—H1C361.000
C33—C341.403 (1)C310—H1C3101.000
C34—C351.403 (1)C310—H2C3101.000
C34—N3121.373 (2)C311—H1C3111.000
C35—C361.381 (2)C311—H2C3111.000
C37—O381.210 (3)C311—H3C3111.000
C37—O391.350 (3)N312—H1N3121.000
O39—C3101.449 (4)N312—H2N3121.000
C310—C3111.502 (5)C42—H1C421.000
C41—C421.394 (1)C43—H1C431.000
C41—C461.394 (1)C45—H1C451.000
C41—C471.474 (2)C46—H1C461.000
C42—C431.381 (2)C410—H1C4101.000
C43—C441.403 (1)C410—H2C4101.000
C44—C451.403 (1)C411—H1C4111.000
C44—N4121.373 (2)C411—H2C4111.000
C45—C461.381 (2)C411—H3C4111.000
C47—O481.212 (3)N412—H1N4121.000
C47—O491.369 (3)N412—H2N4121.000
C11···C211i3.578 (4)C22···C4103.504 (4)
C13···O483.535 (3)C23···C473.527 (3)
C14···N212ii3.382 (3)C23···O493.504 (3)
C15···O18ii3.393 (3)C24···N312iii3.481 (2)
C16···C333.455 (3)C25···O28iii3.423 (3)
O18···N112iii2.941 (3)C26···C43v3.394 (3)
O18···C233.513 (3)O28···N212ii2.941 (3)
O19···C210i3.586 (4)O28···N3123.979 (4)
O19···C323.483 (3)N212···N312iii3.196 (3)
C110···O383.588 (5)C34···N412vi3.438 (3)
C111···O383.547 (5)C35···O38ii3.432 (3)
N112···C44ii3.513 (3)O38···N312iii2.962 (3)
N112···N212ii3.219 (3)O38···C43v3.573 (3)
N112···O39iv3.633 (3)N312···N412vi3.124 (3)
N112···C310iv3.582 (4)C45···O48iii3.414 (3)
N112···C45ii3.571 (3)O48···N412ii2.943 (3)
C22···O493.496 (3)
C12—C11—C16119.1 (1)C110—C111—H2C111109.5
C12—C11—C17118.9 (1)C110—C111—H3C111109.5
C16—C11—C17122.0 (1)H1C111—C111—H2C111109.5
C11—C12—C13120.6 (1)H1C111—C111—H3C111109.5
C12—C13—C14120.5 (1)H2C111—C111—H3C111109.5
C13—C14—C15118.6 (1)C14—N112—H1N112120.0
C13—C14—N112120.8 (1)C14—N112—H2N112120.0
C15—C14—N112120.5 (1)H1N112—N112—H2N112120.0
C14—C15—C16120.5 (1)C21—C22—H1C22119.7
C11—C16—C15120.6 (1)C23—C22—H1C22119.7
C11—C17—O18125.3 (2)C22—C23—H1C23119.8
C11—C17—O19112.8 (2)C24—C23—H1C23119.8
O18—C17—O19121.8 (2)C24—C25—H1C25119.8
C17—O19—C110116.3 (2)C26—C25—H1C25119.8
O19—C110—C111106.6 (3)C21—C26—H1C26119.7
C22—C21—C26119.1 (1)C25—C26—H1C26119.7
C22—C21—C27118.9 (1)O29—C210—H1C210109.9
C26—C21—C27122.0 (1)O29—C210—H2C210109.9
C21—C22—C23120.6 (1)C211—C210—H1C210109.9
C22—C23—C24120.5 (1)C211—C210—H2C210109.9
C23—C24—C25118.6 (1)H1C210—C210—H2C210109.5
C23—C24—N212120.8 (1)C210—C211—H1C211109.5
C25—C24—N212120.5 (1)C210—C211—H2C211109.5
C24—C25—C26120.5 (1)C210—C211—H3C211109.5
C21—C26—C25120.6 (1)H1C211—C211—H2C211109.5
C21—C27—O28124.1 (2)H1C211—C211—H3C211109.5
C21—C27—O29113.7 (2)H2C211—C211—H3C211109.5
O28—C27—O29122.1 (2)C24—N212—H1N212120.0
C27—O29—C210116.1 (2)C24—N212—H2N212120.0
O29—C210—C211107.8 (3)H1N212—N212—H2N212120.0
C32—C31—C36119.1 (1)C31—C32—H1C32119.7
C32—C31—C37118.9 (1)C33—C32—H1C32119.7
C36—C31—C37122.0 (1)C32—C33—H1C33119.8
C31—C32—C33120.6 (1)C34—C33—H1C33119.8
C32—C33—C34120.5 (1)C34—C35—H1C35119.8
C33—C34—C35118.6 (1)C36—C35—H1C35119.8
C33—C34—N312120.8 (1)C31—C36—H1C36119.7
C35—C34—N312120.5 (1)C35—C36—H1C36119.7
C34—C35—C36120.5 (1)O39—C310—H1C310110.0
C31—C36—C35120.6 (1)O39—C310—H2C310110.0
C31—C37—O38125.6 (2)C311—C310—H1C310110.0
C31—C37—O39112.6 (2)C311—C310—H2C310110.0
O38—C37—O39121.5 (2)H1C310—C310—H2C310109.5
C37—O39—C310117.2 (2)C310—C311—H1C311109.5
O39—C310—C311107.4 (3)C310—C311—H2C311109.5
C42—C41—C46119.1 (1)C310—C311—H3C311109.5
C42—C41—C47118.9 (1)H1C311—C311—H2C311109.5
C46—C41—C47122.0 (1)H1C311—C311—H3C311109.5
C41—C42—C43120.6 (1)H2C311—C311—H3C311109.5
C42—C43—C44120.5 (1)C34—N312—H1N312120.0
C43—C44—C45118.6 (1)C34—N312—H2N312120.0
C43—C44—N412120.8 (1)H1N312—N312—H2N312120.0
C45—C44—N412120.5 (1)C41—C42—H1C42119.7
C44—C45—C46120.5 (1)C43—C42—H1C42119.7
C41—C46—C45120.6 (1)C42—C43—H1C43119.8
C41—C47—O48125.4 (2)C44—C43—H1C43119.8
C41—C47—O49111.5 (2)C44—C45—H1C45119.8
O48—C47—O49121.5 (2)C46—C45—H1C45119.8
C47—O49—C410116.5 (2)C41—C46—H1C46119.7
O49—C410—C411107.7 (3)C45—C46—H1C46119.7
C11—C12—H1C12119.7O49—C410—H1C410109.9
C13—C12—H1C12119.7O49—C410—H2C410109.9
C12—C13—H1C13119.8C411—C410—H1C410109.9
C14—C13—H1C13119.8C411—C410—H2C410109.9
C14—C15—H1C15119.8H1C410—C410—H2C410109.5
C16—C15—H1C15119.8C410—C411—H1C411109.5
C11—C16—H1C16119.7C410—C411—H2C411109.5
C15—C16—H1C16119.7C410—C411—H3C411109.5
O19—C110—H1C110110.2H1C411—C411—H2C411109.5
O19—C110—H2C110110.2H1C411—C411—H3C411109.5
C111—C110—H1C110110.2H2C411—C411—H3C411109.5
C111—C110—H2C110110.2C44—N412—H1N412120.0
H1C110—C110—H2C110109.5C44—N412—H2N412120.0
C110—C111—H1C111109.5H1N412—N412—H2N412120.0
C16—C11—C12—C130.0C36—C31—C32—C330.0
C17—C11—C12—C13180.0C37—C31—C32—C33180.0
C12—C11—C16—C150.0C32—C31—C36—C350.0
C17—C11—C16—C15180.0C37—C31—C36—C35180.0
C12—C11—C17—O181.0 (2)C32—C31—C37—O382.6 (2)
C12—C11—C17—O19177.8 (2)C32—C31—C37—O39170.2 (2)
C16—C11—C17—O18179.0 (2)C36—C31—C37—O38177.4 (2)
C16—C11—C17—O192.2 (2)C36—C31—C37—O399.8 (2)
C11—C12—C13—C140.0C31—C32—C33—C340.0
C12—C13—C14—C150.0C32—C33—C34—C350.0
C12—C13—C14—N112180.0C32—C33—C34—N312180.0
C13—C14—C15—C160.0C33—C34—C35—C360.0
N112—C14—C15—C16180.0N312—C34—C35—C36180.0
C14—C15—C16—C110.0C34—C35—C36—C310.0
C11—C17—O19—C110179.4 (2)C31—C37—O39—C310176.7 (2)
O18—C17—O19—C1102.5 (4)O38—C37—O39—C3103.5 (4)
C17—O19—C110—C111175.1 (3)C37—O39—C310—C311173.5 (3)
C26—C21—C22—C230.0C46—C41—C42—C430.0
C27—C21—C22—C23180.0C47—C41—C42—C43180.0
C22—C21—C26—C250.0C42—C41—C46—C450.0
C27—C21—C26—C25180.0C47—C41—C46—C45180.0
C22—C21—C27—O284.2 (2)C42—C41—C47—O484.1 (3)
C22—C21—C27—O29179.6 (2)C42—C41—C47—O49161.6 (2)
C26—C21—C27—O28175.8 (2)C46—C41—C47—O48175.9 (3)
C26—C21—C27—O290.4 (2)C46—C41—C47—O4918.4 (2)
C21—C22—C23—C240.0C41—C42—C43—C440.0
C22—C23—C24—C250.0C42—C43—C44—C450.0
C22—C23—C24—N212180.0C42—C43—C44—N412180.0
C23—C24—C25—C260.0C43—C44—C45—C460.0
N212—C24—C25—C26180.0N412—C44—C45—C46180.0
C24—C25—C26—C210.0C44—C45—C46—C410.0
C21—C27—O29—C210179.3 (2)C41—C47—O49—C410174.2 (2)
O28—C27—O29—C2103.0 (4)O48—C47—O49—C4107.9 (4)
C27—O29—C210—C211179.4 (3)C47—O49—C410—C411173.3 (3)
Symmetry codes: (i) x+1, y+1, z+1/2; (ii) x1, y, z; (iii) x+1, y, z; (iv) x1, y1, z; (v) x, y+1, z; (vi) x1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N112—H2N112···O18ii1.001.982.941 (3)161
N212—H2N212···O28iii1.001.992.941 (3)158
N312—H2N312···O38ii1.002.042.962 (3)153
N412—H2N412···O48iii1.001.992.943 (3)158
N112—H1N112···N412ii1.003.254.094 (3)143
N212—H1N212···N112iii1.002.223.219 (3)176
N312—H1N312···N212ii1.002.203.196 (3)174
N412—H1N412···N312vii1.002.133.124 (3)170
N112—H1N112···C44ii1.002.563.513 (3)160
N212—H1N212···C14iii1.002.483.382 (3)151
N312—H1N312···C24ii1.002.633.481 (2)143
N412—H1N412···C34vii1.002.613.438 (3)141
Symmetry codes: (ii) x1, y, z; (iii) x+1, y, z; (vii) x+1, y1, z.
 

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