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Natural and synthetic iso­quinoline alkaloids display a wide variety of potent biological activities. The title 1-aryl-2-hydroxyethyl-1,2,3,4-tetra­hydro­iso­quino­line, C19H23NO4, crystallizes with two mol­ecules in the asym­metric unit related by pseudo-translation but differing only slightly in conformation. The pseudosymmetry is also reflected in the diffraction pattern. The subset of reflections corresponding to the smaller cell and average structure are on average twice as intense as those subtending the larger cell. Tentative refinement in the subcell leads to a disordered structural model with satisfactory agreement factors and, after appropriate use of restraints, acceptable mol­ecular geometry but significantly larger and more anisotropic displacement parameters. In the correct unit cell, the independent mol­ecules differ with respect to the orientation of the hy­droxy­ethyl group. Intra­molecular hydrogen bonding occurs between the hydroxyphenyl group and the N atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616010792/qs3055sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616010792/qs3055Isup2.hkl
Contains datablock I

txt

Text file https://doi.org/10.1107/S2053229616010792/qs3055sup3.txt
CIF file for supporting information.

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616010792/qs3055Isup4.cml
Supplementary material

mpg

Moving Picture Experts Group (MPG) video file https://doi.org/10.1107/S2053229616010792/qs3055sup5.mpg
Both independent molecules (A and B) and their overlay are shown sequentially in this animation

CCDC reference: 1489810

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009) and SADABS (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2006) and XP (Bruker, 1998); software used to prepare material for publication: PLATON(Spek, 2009).

2-(2-Hydroxyethyl)-1-(2-hydroxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline top
Crystal data top
C19H23NO4F(000) = 704
Mr = 329.38Dx = 1.322 Mg m3
Triclinic, P1Melting point: 423(2) K
a = 7.429 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.535 (4) ÅCell parameters from 1135 reflections
c = 15.675 (4) Åθ = 2.7–26.1°
α = 97.575 (5)°µ = 0.09 mm1
β = 98.902 (5)°T = 100 K
γ = 92.280 (5)°Plate, colourless
V = 1654.5 (8) Å30.27 × 0.23 × 0.12 mm
Z = 4
Data collection top
Bruker D8 gonimeter with APEX CCD detector
diffractometer
6783 independent reflections
Radiation source: Incoatec microsource3681 reflections with I > 2σ(I)
Multilayer optics monochromatorRint = 0.077
ω scansθmax = 26.5°, θmin = 1.3°
Absorption correction: multi-scan
SADABS
h = 99
Tmin = 0.870, Tmax = 1.000k = 1818
15196 measured reflectionsl = 1819
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.069H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.207 w = 1/[σ2(Fo2) + (0.0729P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
6783 reflectionsΔρmax = 0.63 e Å3
450 parametersΔρmin = 0.34 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*/Ueq
O1A0.3448 (3)0.24278 (13)0.06134 (13)0.0195 (5)
O2A0.2966 (3)0.28107 (13)0.22977 (13)0.0168 (5)
O3A0.1844 (3)0.63449 (14)0.22201 (14)0.0200 (5)
O4A0.6188 (3)0.66138 (15)0.15204 (16)0.0352 (6)
C1A0.2990 (4)0.45144 (18)0.24057 (18)0.0147 (6)
H1AA0.37700.40320.26420.018*
N2A0.4025 (3)0.50248 (15)0.18498 (15)0.0159 (6)
C3A0.4158 (4)0.44272 (19)0.10300 (18)0.0184 (7)
H3AB0.46490.38290.11610.022*
H3AC0.50080.47330.07110.022*
C4A0.2292 (4)0.4248 (2)0.04660 (19)0.0196 (7)
H4AB0.18860.48340.02630.023*
H4AC0.23740.37930.00530.023*
C4AA0.0910 (4)0.38763 (18)0.09676 (18)0.0142 (6)
C5A0.0670 (4)0.33535 (18)0.05310 (19)0.0163 (7)
H5AA0.08890.32530.00880.020*
C6A0.1917 (4)0.29820 (18)0.09802 (19)0.0158 (7)
C7A0.1623 (4)0.31675 (18)0.18979 (19)0.0148 (6)
C8A0.0085 (4)0.36796 (18)0.23302 (19)0.0144 (6)
H8AA0.01050.38010.29490.017*
C8AA0.1222 (4)0.40294 (17)0.18712 (18)0.0130 (6)
C9A0.3725 (4)0.2178 (2)0.03157 (19)0.0259 (8)
H9AA0.48510.17800.05020.039*
H9AB0.26900.18400.04840.039*
H9AC0.38240.27420.05960.039*
C10A0.2730 (4)0.30182 (19)0.32285 (18)0.0169 (7)
H10A0.37640.27350.34400.025*
H10B0.26680.36940.33980.025*
H10C0.15960.27680.34840.025*
C11A0.2551 (4)0.51777 (18)0.31612 (19)0.0150 (6)
C12A0.1880 (4)0.60489 (19)0.30116 (19)0.0164 (7)
C13A0.1253 (4)0.6610 (2)0.3680 (2)0.0230 (7)
H13A0.07710.71890.35790.028*
C14A0.1333 (4)0.6326 (2)0.4490 (2)0.0261 (8)
H14A0.08920.67110.49420.031*
C15A0.2047 (4)0.5490 (2)0.4656 (2)0.0247 (7)
H15A0.21100.53050.52190.030*
C16A0.2667 (4)0.4927 (2)0.39925 (19)0.0192 (7)
H16A0.31820.43600.41080.023*
C17A0.5854 (4)0.53435 (19)0.23653 (19)0.0191 (7)
H17A0.64940.47910.25260.023*
H17B0.56770.57270.29130.023*
C18A0.7059 (4)0.5898 (2)0.1906 (2)0.0287 (8)
H18A0.81350.61710.23300.034*
H18B0.75050.54720.14480.034*
O1B1.3476 (3)1.24568 (13)0.44849 (13)0.0209 (5)
O2B1.3051 (3)1.20930 (13)0.27953 (12)0.0171 (5)
O3B0.8447 (3)0.85566 (14)0.27042 (14)0.0211 (5)
O4B0.4333 (3)0.79004 (14)0.26269 (16)0.0321 (6)
H4B0.36270.74190.25400.048*
C1B0.7079 (4)1.03872 (18)0.26227 (18)0.0143 (6)
H1BA0.62871.08780.24110.017*
N2B0.6054 (3)0.98426 (15)0.31472 (15)0.0152 (5)
C3B0.5857 (4)1.04279 (19)0.39695 (19)0.0179 (7)
H3BB0.50091.01020.42750.022*
H3BC0.53331.10190.38370.022*
C4B0.7691 (4)1.0635 (2)0.45557 (19)0.0214 (7)
H4BB0.75621.10940.50650.026*
H4BC0.81131.00580.47730.026*
C4AB0.9088 (4)1.10145 (18)0.40675 (19)0.0153 (6)
C5B1.0653 (4)1.15457 (18)0.45301 (19)0.0164 (7)
H5BA1.08221.16550.51490.020*
C6B1.1944 (4)1.19102 (19)0.40984 (19)0.0174 (7)
C7B1.1692 (4)1.17373 (18)0.31776 (18)0.0147 (6)
C8B1.0152 (4)1.12234 (18)0.27287 (18)0.0159 (7)
H8BA0.99851.11080.21100.019*
C8AB0.8828 (4)1.08680 (18)0.31683 (18)0.0140 (6)
C9B1.3754 (4)1.2652 (2)0.5419 (2)0.0336 (9)
H9BA1.48761.30490.56240.050*
H9BB1.38591.20680.56670.050*
H9BC1.27151.29740.56050.050*
C10B1.2852 (4)1.18878 (19)0.18655 (18)0.0167 (7)
H10D1.39131.21600.16660.025*
H10E1.17411.21510.16000.025*
H10F1.27651.12120.16940.025*
C11B0.7515 (4)0.97668 (18)0.18348 (19)0.0148 (6)
C12B0.8260 (4)0.89027 (18)0.19270 (19)0.0159 (7)
C13B0.8859 (4)0.8394 (2)0.12260 (19)0.0208 (7)
H13B0.93840.78170.12900.025*
C14B0.8695 (4)0.8728 (2)0.0427 (2)0.0252 (8)
H14B0.91250.83810.00490.030*
C15B0.7910 (4)0.9561 (2)0.0319 (2)0.0227 (7)
H15B0.77800.97810.02300.027*
C16B0.7316 (4)1.0070 (2)0.10222 (19)0.0187 (7)
H16B0.67621.06380.09480.022*
C17B0.4210 (4)0.95446 (19)0.2650 (2)0.0199 (7)
H17C0.42920.94180.20210.024*
H17D0.33911.00590.27300.024*
C18B0.3386 (4)0.8684 (2)0.2929 (2)0.0249 (8)
H18C0.35000.87570.35720.030*
H18D0.20740.85920.26780.030*
H3B0.776 (5)0.887 (2)0.296 (2)0.035 (11)*
H3A0.248 (5)0.596 (2)0.192 (2)0.044 (11)*
H4A0.592 (4)0.6996 (17)0.2102 (13)0.015 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0178 (11)0.0203 (11)0.0172 (11)0.0023 (9)0.0013 (9)0.0035 (9)
O2A0.0155 (10)0.0182 (11)0.0163 (11)0.0042 (8)0.0040 (9)0.0002 (8)
O3A0.0224 (12)0.0153 (11)0.0218 (12)0.0022 (9)0.0029 (10)0.0011 (9)
O4A0.0399 (15)0.0299 (13)0.0369 (16)0.0027 (11)0.0049 (12)0.0097 (11)
C1A0.0170 (15)0.0100 (14)0.0167 (16)0.0017 (11)0.0024 (12)0.0014 (12)
N2A0.0153 (12)0.0147 (12)0.0180 (14)0.0008 (10)0.0057 (11)0.0001 (10)
C3A0.0232 (16)0.0172 (15)0.0164 (16)0.0016 (12)0.0106 (13)0.0002 (12)
C4A0.0248 (17)0.0173 (15)0.0161 (17)0.0005 (13)0.0043 (13)0.0001 (12)
C4AA0.0185 (15)0.0091 (14)0.0158 (16)0.0045 (11)0.0048 (12)0.0008 (12)
C5A0.0193 (15)0.0146 (14)0.0145 (16)0.0033 (12)0.0020 (13)0.0006 (12)
C6A0.0125 (14)0.0124 (14)0.0203 (17)0.0025 (11)0.0017 (13)0.0020 (12)
C7A0.0138 (14)0.0116 (14)0.0201 (17)0.0023 (11)0.0054 (12)0.0025 (12)
C8A0.0153 (15)0.0110 (14)0.0160 (16)0.0018 (11)0.0013 (12)0.0002 (12)
C8AA0.0146 (14)0.0074 (13)0.0164 (16)0.0020 (11)0.0026 (12)0.0007 (11)
C9A0.0224 (17)0.0330 (18)0.0178 (18)0.0029 (14)0.0021 (14)0.0055 (14)
C10A0.0185 (15)0.0163 (15)0.0159 (16)0.0007 (12)0.0059 (13)0.0007 (12)
C11A0.0115 (14)0.0115 (14)0.0204 (17)0.0024 (11)0.0016 (12)0.0015 (12)
C12A0.0126 (14)0.0166 (15)0.0185 (17)0.0023 (12)0.0006 (12)0.0001 (12)
C13A0.0170 (16)0.0180 (16)0.031 (2)0.0022 (12)0.0026 (14)0.0034 (14)
C14A0.0244 (17)0.0259 (18)0.0239 (19)0.0032 (14)0.0066 (14)0.0139 (14)
C15A0.0274 (18)0.0311 (18)0.0144 (17)0.0035 (14)0.0042 (14)0.0005 (14)
C16A0.0200 (16)0.0173 (15)0.0195 (17)0.0036 (12)0.0029 (13)0.0018 (13)
C17A0.0161 (15)0.0198 (16)0.0207 (17)0.0001 (12)0.0019 (13)0.0016 (13)
C18A0.0232 (17)0.0342 (19)0.028 (2)0.0044 (14)0.0002 (15)0.0096 (15)
O1B0.0162 (11)0.0231 (11)0.0192 (12)0.0025 (9)0.0023 (9)0.0051 (9)
O2B0.0162 (11)0.0180 (10)0.0160 (11)0.0038 (8)0.0026 (9)0.0004 (8)
O3B0.0250 (12)0.0187 (11)0.0212 (13)0.0071 (10)0.0061 (10)0.0034 (9)
O4B0.0314 (13)0.0213 (12)0.0436 (16)0.0007 (10)0.0096 (12)0.0000 (11)
C1B0.0148 (14)0.0138 (14)0.0133 (16)0.0017 (11)0.0020 (12)0.0004 (12)
N2B0.0135 (12)0.0165 (12)0.0157 (13)0.0000 (10)0.0040 (10)0.0006 (10)
C3B0.0168 (15)0.0179 (15)0.0194 (17)0.0005 (12)0.0067 (13)0.0003 (12)
C4B0.0243 (17)0.0240 (16)0.0157 (17)0.0007 (13)0.0038 (13)0.0017 (13)
C4AB0.0193 (15)0.0083 (13)0.0187 (16)0.0036 (11)0.0041 (13)0.0012 (11)
C5B0.0208 (16)0.0142 (14)0.0131 (16)0.0056 (12)0.0000 (13)0.0004 (12)
C6B0.0168 (15)0.0144 (15)0.0190 (17)0.0026 (12)0.0003 (13)0.0014 (12)
C7B0.0138 (14)0.0131 (14)0.0163 (16)0.0012 (11)0.0024 (12)0.0010 (12)
C8B0.0192 (15)0.0155 (14)0.0119 (16)0.0039 (12)0.0012 (13)0.0012 (12)
C8AB0.0137 (14)0.0120 (14)0.0157 (16)0.0007 (11)0.0040 (12)0.0021 (12)
C9B0.0235 (18)0.053 (2)0.0180 (18)0.0081 (16)0.0012 (14)0.0093 (16)
C10B0.0155 (15)0.0178 (15)0.0159 (16)0.0038 (12)0.0039 (12)0.0002 (12)
C11B0.0098 (14)0.0133 (14)0.0195 (17)0.0022 (11)0.0016 (12)0.0029 (12)
C12B0.0135 (15)0.0127 (14)0.0203 (17)0.0005 (11)0.0008 (13)0.0014 (12)
C13B0.0179 (16)0.0186 (16)0.0243 (19)0.0003 (13)0.0041 (14)0.0033 (13)
C14B0.0205 (16)0.0286 (18)0.0230 (19)0.0033 (13)0.0077 (14)0.0122 (14)
C15B0.0276 (17)0.0251 (17)0.0143 (17)0.0052 (14)0.0030 (14)0.0016 (13)
C16B0.0203 (16)0.0173 (15)0.0159 (17)0.0035 (12)0.0011 (13)0.0012 (12)
C17B0.0157 (15)0.0218 (16)0.0219 (18)0.0028 (12)0.0030 (13)0.0020 (13)
C18B0.0218 (16)0.0216 (16)0.031 (2)0.0008 (13)0.0072 (14)0.0012 (14)
Geometric parameters (Å, º) top
O1A—C6A1.369 (3)O1B—C6B1.371 (3)
O1A—C9A1.434 (3)O1B—C9B1.436 (3)
O2A—C7A1.376 (3)O2B—C7B1.369 (3)
O2A—C10A1.432 (3)O2B—C10B1.432 (3)
O3A—C12A1.363 (3)O3B—C12B1.368 (3)
O3A—H3A0.88 (3)O3B—H3B0.81 (3)
O4A—C18A1.402 (4)O4B—C18B1.428 (3)
O4A—H4A1.054 (17)O4B—H4B0.8400
C1A—N2A1.494 (4)C1B—N2B1.483 (4)
C1A—C11A1.510 (4)C1B—C11B1.516 (4)
C1A—C8AA1.534 (4)C1B—C8AB1.528 (4)
C1A—H1AA1.0000C1B—H1BA1.0000
N2A—C3A1.472 (3)N2B—C3B1.478 (3)
N2A—C17A1.492 (3)N2B—C17B1.485 (3)
C3A—C4A1.518 (4)C3B—C4B1.516 (4)
C3A—H3AB0.9900C3B—H3BB0.9900
C3A—H3AC0.9900C3B—H3BC0.9900
C4A—C4AA1.510 (4)C4B—C4AB1.509 (4)
C4A—H4AB0.9900C4B—H4BB0.9900
C4A—H4AC0.9900C4B—H4BC0.9900
C4AA—C8AA1.386 (4)C4AB—C8AB1.379 (4)
C4AA—C5A1.403 (4)C4AB—C5B1.412 (4)
C5A—C6A1.381 (4)C5B—C6B1.383 (4)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—C7A1.409 (4)C6B—C7B1.414 (4)
C7A—C8A1.371 (4)C7B—C8B1.380 (4)
C8A—C8AA1.411 (4)C8B—C8AB1.405 (4)
C8A—H8AA0.9500C8B—H8BA0.9500
C9A—H9AA0.9800C9B—H9BA0.9800
C9A—H9AB0.9800C9B—H9BB0.9800
C9A—H9AC0.9800C9B—H9BC0.9800
C10A—H10A0.9800C10B—H10D0.9800
C10A—H10B0.9800C10B—H10E0.9800
C10A—H10C0.9800C10B—H10F0.9800
C11A—C16A1.389 (4)C11B—C16B1.390 (4)
C11A—C12A1.414 (4)C11B—C12B1.408 (4)
C12A—C13A1.392 (4)C12B—C13B1.384 (4)
C13A—C14A1.379 (4)C13B—C14B1.392 (4)
C13A—H13A0.9500C13B—H13B0.9500
C14A—C15A1.385 (4)C14B—C15B1.383 (4)
C14A—H14A0.9500C14B—H14B0.9500
C15A—C16A1.385 (4)C15B—C16B1.385 (4)
C15A—H15A0.9500C15B—H15B0.9500
C16A—H16A0.9500C16B—H16B0.9500
C17A—C18A1.505 (4)C17B—C18B1.516 (4)
C17A—H17A0.9900C17B—H17C0.9900
C17A—H17B0.9900C17B—H17D0.9900
C18A—H18A0.9900C18B—H18C0.9900
C18A—H18B0.9900C18B—H18D0.9900
C6A—O1A—C9A116.8 (2)C6B—O1B—C9B116.4 (2)
C7A—O2A—C10A116.6 (2)C7B—O2B—C10B116.5 (2)
C12A—O3A—H3A106 (2)C12B—O3B—H3B101 (2)
C18A—O4A—H4A96.6 (15)C18B—O4B—H4B109.5
N2A—C1A—C11A110.1 (2)N2B—C1B—C11B110.4 (2)
N2A—C1A—C8AA110.9 (2)N2B—C1B—C8AB111.4 (2)
C11A—C1A—C8AA109.9 (2)C11B—C1B—C8AB110.4 (2)
N2A—C1A—H1AA108.6N2B—C1B—H1BA108.2
C11A—C1A—H1AA108.6C11B—C1B—H1BA108.2
C8AA—C1A—H1AA108.6C8AB—C1B—H1BA108.2
C3A—N2A—C17A112.3 (2)C3B—N2B—C1B109.5 (2)
C3A—N2A—C1A110.4 (2)C3B—N2B—C17B109.0 (2)
C17A—N2A—C1A108.1 (2)C1B—N2B—C17B109.5 (2)
N2A—C3A—C4A110.2 (2)N2B—C3B—C4B110.7 (2)
N2A—C3A—H3AB109.6N2B—C3B—H3BB109.5
C4A—C3A—H3AB109.6C4B—C3B—H3BB109.5
N2A—C3A—H3AC109.6N2B—C3B—H3BC109.5
C4A—C3A—H3AC109.6C4B—C3B—H3BC109.5
H3AB—C3A—H3AC108.1H3BB—C3B—H3BC108.1
C4AA—C4A—C3A111.0 (2)C4AB—C4B—C3B110.8 (2)
C4AA—C4A—H4AB109.4C4AB—C4B—H4BB109.5
C3A—C4A—H4AB109.4C3B—C4B—H4BB109.5
C4AA—C4A—H4AC109.4C4AB—C4B—H4BC109.5
C3A—C4A—H4AC109.4C3B—C4B—H4BC109.5
H4AB—C4A—H4AC108.0H4BB—C4B—H4BC108.1
C8AA—C4AA—C5A119.2 (3)C8AB—C4AB—C5B119.4 (3)
C8AA—C4AA—C4A119.9 (3)C8AB—C4AB—C4B120.6 (3)
C5A—C4AA—C4A120.8 (3)C5B—C4AB—C4B120.0 (3)
C6A—C5A—C4AA121.6 (3)C6B—C5B—C4AB121.2 (3)
C6A—C5A—H5AA119.2C6B—C5B—H5BA119.4
C4AA—C5A—H5AA119.2C4AB—C5B—H5BA119.4
O1A—C6A—C5A125.7 (3)O1B—C6B—C5B125.7 (3)
O1A—C6A—C7A115.4 (3)O1B—C6B—C7B115.2 (3)
C5A—C6A—C7A118.9 (3)C5B—C6B—C7B119.1 (3)
C8A—C7A—O2A124.5 (3)O2B—C7B—C8B124.6 (3)
C8A—C7A—C6A119.9 (3)O2B—C7B—C6B115.9 (2)
O2A—C7A—C6A115.5 (2)C8B—C7B—C6B119.4 (3)
C7A—C8A—C8AA121.1 (3)C7B—C8B—C8AB121.3 (3)
C7A—C8A—H8AA119.5C7B—C8B—H8BA119.3
C8AA—C8A—H8AA119.5C8AB—C8B—H8BA119.3
C4AA—C8AA—C8A119.2 (3)C4AB—C8AB—C8B119.5 (3)
C4AA—C8AA—C1A122.9 (3)C4AB—C8AB—C1B122.3 (3)
C8A—C8AA—C1A117.7 (2)C8B—C8AB—C1B118.1 (2)
O1A—C9A—H9AA109.5O1B—C9B—H9BA109.5
O1A—C9A—H9AB109.5O1B—C9B—H9BB109.5
H9AA—C9A—H9AB109.5H9BA—C9B—H9BB109.5
O1A—C9A—H9AC109.5O1B—C9B—H9BC109.5
H9AA—C9A—H9AC109.5H9BA—C9B—H9BC109.5
H9AB—C9A—H9AC109.5H9BB—C9B—H9BC109.5
O2A—C10A—H10A109.5O2B—C10B—H10D109.5
O2A—C10A—H10B109.5O2B—C10B—H10E109.5
H10A—C10A—H10B109.5H10D—C10B—H10E109.5
O2A—C10A—H10C109.5O2B—C10B—H10F109.5
H10A—C10A—H10C109.5H10D—C10B—H10F109.5
H10B—C10A—H10C109.5H10E—C10B—H10F109.5
C16A—C11A—C12A118.8 (3)C16B—C11B—C12B118.8 (3)
C16A—C11A—C1A121.5 (2)C16B—C11B—C1B120.6 (2)
C12A—C11A—C1A119.5 (3)C12B—C11B—C1B120.4 (3)
O3A—C12A—C13A119.7 (3)O3B—C12B—C13B118.6 (2)
O3A—C12A—C11A120.7 (2)O3B—C12B—C11B121.5 (3)
C13A—C12A—C11A119.7 (3)C13B—C12B—C11B119.9 (3)
C14A—C13A—C12A120.0 (3)C12B—C13B—C14B120.1 (3)
C14A—C13A—H13A120.0C12B—C13B—H13B120.0
C12A—C13A—H13A120.0C14B—C13B—H13B120.0
C13A—C14A—C15A121.1 (3)C15B—C14B—C13B120.7 (3)
C13A—C14A—H14A119.4C15B—C14B—H14B119.7
C15A—C14A—H14A119.4C13B—C14B—H14B119.7
C16A—C15A—C14A119.1 (3)C14B—C15B—C16B119.1 (3)
C16A—C15A—H15A120.4C14B—C15B—H15B120.4
C14A—C15A—H15A120.4C16B—C15B—H15B120.4
C15A—C16A—C11A121.2 (3)C15B—C16B—C11B121.4 (3)
C15A—C16A—H16A119.4C15B—C16B—H16B119.3
C11A—C16A—H16A119.4C11B—C16B—H16B119.3
N2A—C17A—C18A114.9 (2)N2B—C17B—C18B112.9 (2)
N2A—C17A—H17A108.5N2B—C17B—H17C109.0
C18A—C17A—H17A108.5C18B—C17B—H17C109.0
N2A—C17A—H17B108.5N2B—C17B—H17D109.0
C18A—C17A—H17B108.5C18B—C17B—H17D109.0
H17A—C17A—H17B107.5H17C—C17B—H17D107.8
O4A—C18A—C17A113.8 (3)O4B—C18B—C17B108.6 (2)
O4A—C18A—H18A108.8O4B—C18B—H18C110.0
C17A—C18A—H18A108.8C17B—C18B—H18C110.0
O4A—C18A—H18B108.8O4B—C18B—H18D110.0
C17A—C18A—H18B108.8C17B—C18B—H18D110.0
H18A—C18A—H18B107.7H18C—C18B—H18D108.4
C11A—C1A—N2A—C3A169.4 (2)C11B—C1B—N2B—C3B172.5 (2)
C8AA—C1A—N2A—C3A47.6 (3)C8AB—C1B—N2B—C3B49.5 (3)
C11A—C1A—N2A—C17A67.4 (3)C11B—C1B—N2B—C17B68.1 (3)
C8AA—C1A—N2A—C17A170.7 (2)C8AB—C1B—N2B—C17B168.9 (2)
C17A—N2A—C3A—C4A171.1 (2)C1B—N2B—C3B—C4B68.2 (3)
C1A—N2A—C3A—C4A68.3 (3)C17B—N2B—C3B—C4B172.0 (2)
N2A—C3A—C4A—C4AA53.1 (3)N2B—C3B—C4B—C4AB51.6 (3)
C3A—C4A—C4AA—C8AA21.6 (3)C3B—C4B—C4AB—C8AB20.3 (4)
C3A—C4A—C4AA—C5A156.6 (2)C3B—C4B—C4AB—C5B158.0 (2)
C8AA—C4AA—C5A—C6A0.5 (4)C8AB—C4AB—C5B—C6B1.0 (4)
C4A—C4AA—C5A—C6A177.8 (2)C4B—C4AB—C5B—C6B179.3 (2)
C9A—O1A—C6A—C5A3.2 (4)C9B—O1B—C6B—C5B0.8 (4)
C9A—O1A—C6A—C7A176.2 (2)C9B—O1B—C6B—C7B179.3 (2)
C4AA—C5A—C6A—O1A176.7 (2)C4AB—C5B—C6B—O1B177.9 (2)
C4AA—C5A—C6A—C7A2.7 (4)C4AB—C5B—C6B—C7B0.6 (4)
C10A—O2A—C7A—C8A1.6 (4)C10B—O2B—C7B—C8B1.7 (4)
C10A—O2A—C7A—C6A177.8 (2)C10B—O2B—C7B—C6B177.3 (2)
O1A—C6A—C7A—C8A177.0 (2)O1B—C6B—C7B—O2B3.4 (3)
C5A—C6A—C7A—C8A2.4 (4)C5B—C6B—C7B—O2B177.9 (2)
O1A—C6A—C7A—O2A3.5 (3)O1B—C6B—C7B—C8B177.6 (2)
C5A—C6A—C7A—O2A177.1 (2)C5B—C6B—C7B—C8B1.1 (4)
O2A—C7A—C8A—C8AA179.4 (2)O2B—C7B—C8B—C8AB179.0 (2)
C6A—C7A—C8A—C8AA0.1 (4)C6B—C7B—C8B—C8AB0.0 (4)
C5A—C4AA—C8AA—C8A1.9 (4)C5B—C4AB—C8AB—C8B2.1 (4)
C4A—C4AA—C8AA—C8A179.8 (2)C4B—C4AB—C8AB—C8B179.6 (2)
C5A—C4AA—C8AA—C1A174.2 (2)C5B—C4AB—C8AB—C1B173.6 (2)
C4A—C4AA—C8AA—C1A4.0 (4)C4B—C4AB—C8AB—C1B4.7 (4)
C7A—C8A—C8AA—C4AA2.1 (4)C7B—C8B—C8AB—C4AB1.6 (4)
C7A—C8A—C8AA—C1A174.2 (2)C7B—C8B—C8AB—C1B174.2 (2)
N2A—C1A—C8AA—C4AA16.5 (3)N2B—C1B—C8AB—C4AB19.1 (3)
C11A—C1A—C8AA—C4AA138.5 (3)C11B—C1B—C8AB—C4AB142.2 (3)
N2A—C1A—C8AA—C8A167.3 (2)N2B—C1B—C8AB—C8B165.2 (2)
C11A—C1A—C8AA—C8A45.3 (3)C11B—C1B—C8AB—C8B42.1 (3)
N2A—C1A—C11A—C16A139.8 (3)N2B—C1B—C11B—C16B137.2 (3)
C8AA—C1A—C11A—C16A97.7 (3)C8AB—C1B—C11B—C16B99.1 (3)
N2A—C1A—C11A—C12A44.8 (3)N2B—C1B—C11B—C12B47.7 (3)
C8AA—C1A—C11A—C12A77.6 (3)C8AB—C1B—C11B—C12B76.0 (3)
C16A—C11A—C12A—O3A176.1 (2)C16B—C11B—C12B—O3B178.3 (2)
C1A—C11A—C12A—O3A8.4 (4)C1B—C11B—C12B—O3B6.5 (4)
C16A—C11A—C12A—C13A3.7 (4)C16B—C11B—C12B—C13B3.1 (4)
C1A—C11A—C12A—C13A171.7 (3)C1B—C11B—C12B—C13B172.1 (2)
O3A—C12A—C13A—C14A178.2 (3)O3B—C12B—C13B—C14B179.8 (3)
C11A—C12A—C13A—C14A1.7 (4)C11B—C12B—C13B—C14B1.2 (4)
C12A—C13A—C14A—C15A0.6 (4)C12B—C13B—C14B—C15B1.0 (4)
C13A—C14A—C15A—C16A0.8 (5)C13B—C14B—C15B—C16B1.1 (4)
C14A—C15A—C16A—C11A1.4 (4)C14B—C15B—C16B—C11B0.8 (4)
C12A—C11A—C16A—C15A3.6 (4)C12B—C11B—C16B—C15B2.9 (4)
C1A—C11A—C16A—C15A171.8 (3)C1B—C11B—C16B—C15B172.2 (3)
C3A—N2A—C17A—C18A59.7 (3)C3B—N2B—C17B—C18B84.7 (3)
C1A—N2A—C17A—C18A178.3 (2)C1B—N2B—C17B—C18B155.6 (2)
N2A—C17A—C18A—O4A48.4 (3)N2B—C17B—C18B—O4B72.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3A—H3A···N2A0.88 (3)1.82 (4)2.625 (3)152 (3)
O3B—H3B···N2B0.81 (3)1.96 (3)2.728 (3)157 (3)
O4A—H4A···O4B1.05 (2)1.98 (2)2.915 (3)146 (2)
O4B—H4B···O3A0.841.972.803 (3)174
C10A—H10A···O2Bi0.982.523.295 (3)137
C10B—H10D···O2Aii0.982.473.270 (3)138
Symmetry codes: (i) x2, y1, z; (ii) x+2, y+1, z.
Analysis of systematic absences top
NumberExtinction conditionAverage [I/σ(I)]Number of reflectionsI/σ(I)T/F
TrueFalseTrueFalseMax. FhklRatio
1hkl:h + k = 2N3.043.027596758312.64-2-311.0
2hkl:h + l = 2N3.023.047600757912.64-2-311.0
3 > Ahkl:k + l = 2N4.141.937567761211.43-1-182.1
 

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