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The asymmetric unit of the title compound, C21H24NO5+·Cl, contains two crystallographically independent cations and two chloride ions. The crystal structure is stabilized by intra­molecular O—H...O, and inter­molecular N—H...Cl and O—H...Cl hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049300/fl2079sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049300/fl2079Isup2.hkl
Contains datablock I

CCDC reference: 629678

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.075
  • wR factor = 0.225
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.96 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.27 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C18 .. 6.29 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C18 - C19 .. 6.59 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C18 - C19 ... 1.40 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

Diethyl{2-[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7- yloxy]ethyl}ammonium chloride top
Crystal data top
C21H24NO5+·ClZ = 4
Mr = 405.86F(000) = 856
Triclinic, P1Dx = 1.321 Mg m3
a = 7.4420 (15) ÅMo Kα radiation, λ = 0.71073 Å
b = 15.092 (3) ÅCell parameters from 2356 reflections
c = 18.353 (4) Åθ = 2.4–24.9°
α = 89.48 (3)°µ = 0.22 mm1
β = 82.20 (3)°T = 293 K
γ = 88.21 (3)°Block, colourless
V = 2041.2 (7) Å30.40 × 0.30 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
8003 independent reflections
Radiation source: fine-focus sealed tube4500 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 26.0°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 09
Tmin = 0.918, Tmax = 0.979k = 1818
8658 measured reflectionsl = 2222
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)] = 0.075Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.225H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0959P)2 + 2.9117P]
where P = (Fo2 + 2Fc2)/3
7185 reflections(Δ/σ)max < 0.001
521 parametersΔρmax = 0.94 e Å3
870 restraintsΔρmin = 0.75 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
C10.8960 (7)0.8295 (3)0.2098 (3)0.0477 (9)
C20.7157 (7)0.8321 (3)0.2376 (3)0.0496 (9)
H20.63340.86480.21350.060*
C30.6551 (7)0.7863 (3)0.3015 (3)0.0473 (8)
H30.53220.78880.31980.057*
C40.7745 (6)0.7364 (3)0.3390 (3)0.0412 (8)
C50.9558 (7)0.7337 (3)0.3086 (3)0.0438 (8)
H51.03820.69970.33170.053*
C61.0180 (7)0.7797 (3)0.2454 (3)0.0464 (9)
H61.14070.77740.22680.056*
C70.7103 (6)0.6923 (3)0.4097 (3)0.0404 (8)
C80.5899 (6)0.7318 (3)0.4606 (3)0.0418 (8)
H80.54860.78830.44900.050*
C90.5788 (6)0.6156 (3)0.5460 (2)0.0381 (8)
C100.5036 (6)0.5848 (3)0.6138 (2)0.0407 (8)
H100.42040.61900.64490.049*
C110.5584 (6)0.4992 (3)0.6338 (2)0.0397 (8)
C120.6844 (6)0.4491 (3)0.5869 (2)0.0404 (8)
H120.72000.39280.60150.049*
C130.7561 (6)0.4811 (3)0.5201 (2)0.0372 (8)
C140.7054 (6)0.5675 (3)0.4968 (2)0.0363 (7)
C150.7768 (6)0.6027 (3)0.4263 (3)0.0388 (7)
C160.3474 (7)0.5033 (3)0.7436 (3)0.0496 (9)
H16A0.25130.52130.71530.059*
H16B0.39260.55610.76370.059*
C170.2739 (7)0.4427 (4)0.8051 (3)0.0543 (10)
H17A0.15460.46510.82600.065*
H17B0.25930.38460.78490.065*
C180.2764 (9)0.4106 (4)0.9377 (3)0.0700 (12)
H18A0.35240.41420.97650.084*
H18B0.17920.45500.94760.084*
C190.2007 (12)0.3270 (5)0.9404 (4)0.107 (2)
H19A0.13340.32090.89970.160*
H19B0.12090.32050.98570.160*
H19C0.29570.28220.93750.160*
C200.5530 (8)0.3729 (4)0.8445 (3)0.0622 (11)
H20A0.51450.31220.84290.075*
H20B0.61010.38870.79570.075*
C210.6892 (9)0.3783 (5)0.8971 (4)0.0838 (17)
H21A0.73890.43630.89450.126*
H21B0.78490.33470.88430.126*
H21C0.63130.36720.94610.126*
C221.0318 (7)0.3353 (3)0.2052 (3)0.0495 (10)
C231.1450 (8)0.3325 (3)0.2582 (3)0.0516 (9)
H231.25360.36230.25090.062*
C241.0978 (7)0.2854 (3)0.3222 (3)0.0481 (8)
H241.17680.28310.35740.058*
C250.9356 (7)0.2411 (3)0.3356 (3)0.0431 (8)
C260.8216 (7)0.2459 (3)0.2819 (3)0.0464 (8)
H260.71120.21770.28960.056*
C270.8697 (7)0.2921 (3)0.2169 (3)0.0489 (9)
H270.79240.29400.18110.059*
C280.8900 (7)0.1926 (3)0.4057 (3)0.0420 (8)
C290.9271 (7)0.2282 (3)0.4678 (3)0.0450 (8)
H290.97440.28460.46430.054*
C300.8375 (7)0.1061 (3)0.5417 (3)0.0420 (8)
C310.8274 (7)0.0695 (3)0.6110 (3)0.0443 (8)
H310.86200.10060.65010.053*
C320.7630 (7)0.0160 (3)0.6200 (3)0.0434 (8)
C330.7107 (6)0.0617 (3)0.5612 (2)0.0424 (8)
H330.66660.11850.56840.051*
C340.7236 (6)0.0238 (3)0.4933 (2)0.0399 (8)
C350.7885 (6)0.0637 (3)0.4810 (2)0.0396 (8)
C360.8100 (6)0.1043 (3)0.4095 (3)0.0410 (8)
C370.8292 (7)0.0207 (3)0.7434 (3)0.0504 (9)
H37A0.75890.03250.75940.061*
H37B0.95240.00380.72590.061*
C380.8301 (7)0.0836 (4)0.8065 (3)0.0550 (10)
H38A0.93190.07060.83210.066*
H38B0.84960.14330.78720.066*
C390.6863 (8)0.1324 (4)0.9290 (3)0.0626 (12)
H39A0.57100.13370.96070.075*
H39B0.72220.19300.91540.075*
C400.8216 (9)0.0963 (5)0.9702 (3)0.0816 (17)
H40A0.94050.10610.94340.122*
H40B0.81520.12521.01730.122*
H40C0.79820.03380.97720.122*
C410.5005 (8)0.1124 (4)0.8275 (3)0.0644 (12)
H41A0.50230.08660.77890.077*
H41B0.51060.17630.82210.077*
C420.3239 (9)0.0883 (5)0.8728 (4)0.0888 (18)
H42A0.31470.11980.91880.133*
H42B0.22590.10390.84690.133*
H42C0.31760.02570.88190.133*
Cl10.3662 (2)0.87806 (9)0.10473 (8)0.0607 (4)
Cl20.4884 (2)0.37761 (9)0.10639 (8)0.0618 (4)
H1B0.433 (8)0.492 (4)0.869 (3)0.08 (2)*
H2B0.649 (8)0.031 (4)0.871 (3)0.057 (18)*
N10.3889 (6)0.4328 (3)0.8650 (2)0.0462 (10)
N20.6608 (6)0.0811 (3)0.8608 (2)0.0451 (10)
O10.9498 (6)0.8768 (3)0.1473 (2)0.0720 (12)
H11.06070.87380.13800.108*
O20.5213 (4)0.69930 (19)0.52675 (17)0.0450 (8)
O30.8856 (4)0.5587 (2)0.38161 (17)0.0456 (8)
O40.8740 (5)0.4308 (2)0.47495 (18)0.0468 (8)
H40.89450.45540.43480.070*
O50.4907 (5)0.4590 (2)0.69692 (17)0.0491 (9)
O61.0736 (6)0.3807 (3)0.1404 (2)0.0740 (12)
H6A1.18410.38440.13100.111*
O70.9030 (5)0.1906 (2)0.53519 (17)0.0534 (9)
O80.7656 (5)0.0673 (2)0.35447 (17)0.0510 (9)
O90.6745 (5)0.0692 (2)0.43636 (18)0.0546 (9)
H90.69920.04070.39820.082*
O100.7527 (5)0.0609 (2)0.68501 (17)0.0513 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.052 (2)0.0424 (19)0.0494 (19)0.0046 (17)0.0098 (17)0.0046 (17)
C20.0502 (18)0.0450 (18)0.0546 (18)0.0019 (17)0.0124 (17)0.0085 (16)
C30.0478 (17)0.0409 (16)0.0535 (17)0.0024 (15)0.0084 (15)0.0047 (15)
C40.0441 (16)0.0328 (15)0.0477 (16)0.0035 (14)0.0091 (14)0.0003 (14)
C50.0460 (16)0.0369 (16)0.0495 (16)0.0022 (15)0.0106 (15)0.0025 (14)
C60.0468 (18)0.0404 (18)0.0520 (18)0.0029 (16)0.0065 (16)0.0008 (16)
C70.0415 (15)0.0318 (14)0.0489 (15)0.0033 (13)0.0093 (14)0.0000 (13)
C80.0442 (16)0.0305 (15)0.0504 (16)0.0013 (14)0.0059 (15)0.0018 (14)
C90.0379 (16)0.0301 (15)0.0475 (16)0.0033 (14)0.0095 (14)0.0017 (14)
C100.0425 (16)0.0336 (15)0.0465 (16)0.0023 (14)0.0076 (14)0.0029 (14)
C110.0417 (17)0.0359 (16)0.0434 (17)0.0044 (15)0.0115 (15)0.0004 (14)
C120.0410 (17)0.0326 (16)0.0492 (17)0.0014 (15)0.0116 (15)0.0037 (14)
C130.0356 (16)0.0304 (16)0.0471 (16)0.0015 (14)0.0105 (15)0.0025 (14)
C140.0365 (15)0.0292 (14)0.0444 (15)0.0021 (13)0.0102 (14)0.0012 (13)
C150.0389 (15)0.0315 (14)0.0475 (15)0.0041 (13)0.0105 (13)0.0022 (13)
C160.0556 (19)0.0472 (18)0.0470 (18)0.0014 (17)0.0111 (17)0.0004 (16)
C170.059 (2)0.054 (2)0.051 (2)0.0043 (19)0.0127 (19)0.0009 (18)
C180.077 (3)0.073 (2)0.061 (2)0.004 (2)0.015 (2)0.009 (2)
C190.111 (4)0.109 (4)0.101 (4)0.012 (4)0.015 (4)0.009 (4)
C200.068 (2)0.062 (2)0.058 (2)0.005 (2)0.015 (2)0.001 (2)
C210.082 (4)0.083 (4)0.089 (4)0.013 (3)0.027 (3)0.007 (3)
C220.058 (2)0.0388 (18)0.0529 (19)0.0008 (17)0.0111 (18)0.0066 (17)
C230.0574 (19)0.0428 (18)0.0555 (19)0.0062 (17)0.0108 (17)0.0059 (16)
C240.0542 (17)0.0390 (16)0.0524 (17)0.0022 (15)0.0121 (15)0.0039 (15)
C250.0504 (16)0.0312 (15)0.0481 (16)0.0016 (14)0.0085 (15)0.0005 (14)
C260.0523 (17)0.0352 (16)0.0521 (17)0.0024 (15)0.0096 (15)0.0025 (14)
C270.0549 (19)0.0402 (18)0.0533 (18)0.0033 (16)0.0148 (17)0.0038 (16)
C280.0487 (16)0.0303 (14)0.0475 (15)0.0013 (14)0.0083 (14)0.0008 (13)
C290.0544 (17)0.0301 (15)0.0503 (16)0.0010 (15)0.0065 (15)0.0000 (14)
C300.0490 (17)0.0297 (15)0.0465 (16)0.0009 (14)0.0042 (15)0.0013 (14)
C310.0526 (17)0.0350 (15)0.0451 (16)0.0008 (15)0.0056 (15)0.0031 (14)
C320.0475 (17)0.0366 (16)0.0450 (17)0.0022 (15)0.0028 (15)0.0007 (15)
C330.0478 (17)0.0322 (16)0.0465 (17)0.0011 (15)0.0040 (15)0.0014 (14)
C340.0449 (17)0.0300 (16)0.0446 (16)0.0004 (15)0.0052 (15)0.0007 (14)
C350.0449 (16)0.0299 (14)0.0438 (15)0.0015 (14)0.0062 (14)0.0013 (13)
C360.0457 (15)0.0307 (14)0.0468 (15)0.0026 (13)0.0073 (14)0.0013 (13)
C370.0550 (19)0.0479 (18)0.0477 (18)0.0005 (17)0.0043 (17)0.0005 (16)
C380.054 (2)0.058 (2)0.052 (2)0.0024 (19)0.0050 (19)0.0021 (18)
C390.067 (2)0.065 (2)0.055 (2)0.005 (2)0.007 (2)0.004 (2)
C400.085 (4)0.097 (4)0.063 (3)0.001 (3)0.013 (3)0.012 (3)
C410.062 (2)0.069 (2)0.063 (2)0.006 (2)0.007 (2)0.004 (2)
C420.064 (4)0.099 (4)0.102 (4)0.010 (3)0.004 (3)0.013 (4)
Cl10.0691 (9)0.0461 (7)0.0627 (8)0.0005 (7)0.0056 (7)0.0005 (6)
Cl20.0749 (10)0.0543 (8)0.0595 (8)0.0115 (7)0.0182 (7)0.0022 (6)
N10.053 (3)0.045 (2)0.041 (2)0.003 (2)0.0096 (19)0.0029 (19)
N20.049 (3)0.042 (3)0.043 (2)0.002 (2)0.0000 (19)0.002 (2)
O10.068 (3)0.087 (3)0.061 (2)0.006 (2)0.008 (2)0.033 (2)
O20.054 (2)0.0239 (16)0.053 (2)0.0057 (15)0.0037 (16)0.0021 (14)
O30.049 (2)0.0364 (17)0.0488 (19)0.0040 (15)0.0001 (16)0.0020 (14)
O40.047 (2)0.0313 (17)0.060 (2)0.0065 (15)0.0009 (17)0.0008 (15)
O50.053 (2)0.046 (2)0.0462 (19)0.0035 (16)0.0025 (16)0.0066 (15)
O60.074 (3)0.082 (3)0.067 (3)0.009 (3)0.015 (2)0.035 (2)
O70.088 (3)0.0272 (17)0.0450 (19)0.0085 (17)0.0084 (18)0.0034 (14)
O80.069 (2)0.0422 (19)0.0439 (19)0.0120 (17)0.0112 (17)0.0004 (15)
O90.077 (3)0.0393 (19)0.051 (2)0.0188 (18)0.017 (2)0.0027 (16)
O100.068 (2)0.0430 (19)0.0437 (19)0.0034 (17)0.0093 (17)0.0067 (15)
Geometric parameters (Å, º) top
C1—O11.365 (6)C23—C241.377 (7)
C1—C21.369 (7)C23—H230.9300
C1—C61.388 (7)C24—C251.390 (7)
C2—C31.384 (7)C24—H240.9300
C2—H20.9300C25—C261.385 (7)
C3—C41.394 (7)C25—C281.479 (6)
C3—H30.9300C26—C271.386 (7)
C4—C51.388 (7)C26—H260.9300
C4—C71.481 (6)C27—H270.9300
C5—C61.379 (6)C28—C291.330 (6)
C5—H50.9300C28—C361.473 (6)
C6—H60.9300C29—O71.349 (5)
C7—C81.335 (6)C29—H290.9300
C7—C151.468 (6)C30—C311.375 (6)
C8—O21.346 (5)C30—O71.378 (5)
C8—H80.9300C30—C351.386 (6)
C9—C101.377 (6)C31—C321.391 (6)
C9—O21.379 (5)C31—H310.9300
C9—C141.402 (6)C32—O101.361 (5)
C10—C111.402 (6)C32—C331.392 (6)
C10—H100.9300C33—C341.360 (6)
C11—O51.347 (5)C33—H330.9300
C11—C121.393 (6)C34—O91.351 (5)
C12—C131.359 (6)C34—C351.425 (6)
C12—H120.9300C35—C361.434 (6)
C13—O41.344 (5)C36—O81.247 (5)
C13—C141.426 (6)C37—O101.428 (6)
C14—C151.435 (6)C37—C381.490 (7)
C15—O31.251 (5)C37—H37A0.9700
C16—O51.427 (6)C37—H37B0.9700
C16—C171.502 (7)C38—N21.497 (6)
C16—H16A0.9700C38—H38A0.9700
C16—H16B0.9700C38—H38B0.9700
C17—N11.486 (6)C39—C401.461 (8)
C17—H17A0.9700C39—N21.495 (7)
C17—H17B0.9700C39—H39A0.9700
C18—C191.396 (9)C39—H39B0.9700
C18—N11.516 (7)C40—H40A0.9600
C18—H18A0.9700C40—H40B0.9600
C18—H18B0.9700C40—H40C0.9600
C19—H19A0.9600C41—C421.493 (8)
C19—H19B0.9600C41—N21.503 (7)
C19—H19C0.9600C41—H41A0.9700
C20—C211.495 (8)C41—H41B0.9700
C20—N11.504 (7)C42—H42A0.9600
C20—H20A0.9700C42—H42B0.9600
C20—H20B0.9700C42—H42C0.9600
C21—H21A0.9600N1—H1B0.96 (6)
C21—H21B0.9600N2—H2B0.78 (5)
C21—H21C0.9600O1—H10.8200
C22—C231.369 (7)O4—H40.8200
C22—O61.371 (6)O6—H6A0.8200
C22—C271.380 (7)O9—H90.8200
O1—C1—C2118.3 (5)C26—C25—C28122.8 (4)
O1—C1—C6122.1 (5)C24—C25—C28119.8 (4)
C2—C1—C6119.6 (5)C25—C26—C27120.9 (5)
C1—C2—C3120.4 (5)C25—C26—H26119.5
C1—C2—H2119.8C27—C26—H26119.5
C3—C2—H2119.8C22—C27—C26120.2 (5)
C2—C3—C4121.3 (5)C22—C27—H27119.9
C2—C3—H3119.3C26—C27—H27119.9
C4—C3—H3119.3C29—C28—C36118.2 (4)
C5—C4—C3116.9 (4)C29—C28—C25119.2 (4)
C5—C4—C7122.1 (4)C36—C28—C25122.6 (4)
C3—C4—C7120.9 (4)C28—C29—O7126.4 (4)
C6—C5—C4122.2 (5)C28—C29—H29116.8
C6—C5—H5118.9O7—C29—H29116.8
C4—C5—H5118.9C31—C30—O7115.1 (4)
C5—C6—C1119.5 (5)C31—C30—C35124.6 (4)
C5—C6—H6120.3O7—C30—C35120.3 (4)
C1—C6—H6120.3C30—C31—C32117.0 (4)
C8—C7—C15117.4 (4)C30—C31—H31121.5
C8—C7—C4121.6 (4)C32—C31—H31121.5
C15—C7—C4120.9 (4)O10—C32—C31122.9 (4)
C7—C8—O2127.5 (4)O10—C32—C33116.1 (4)
C7—C8—H8116.2C31—C32—C33121.0 (4)
O2—C8—H8116.2C34—C33—C32120.5 (4)
C10—C9—O2116.0 (4)C34—C33—H33119.8
C10—C9—C14124.4 (4)C32—C33—H33119.8
O2—C9—C14119.6 (4)O9—C34—C33119.9 (4)
C9—C10—C11116.8 (4)O9—C34—C35119.2 (4)
C9—C10—H10121.6C33—C34—C35120.8 (4)
C11—C10—H10121.6C30—C35—C34116.1 (4)
O5—C11—C12115.6 (4)C30—C35—C36121.6 (4)
O5—C11—C10123.4 (4)C34—C35—C36122.2 (4)
C12—C11—C10120.9 (4)O8—C36—C35122.5 (4)
C13—C12—C11121.1 (4)O8—C36—C28122.4 (4)
C13—C12—H12119.5C35—C36—C28115.2 (4)
C11—C12—H12119.5O10—C37—C38110.3 (4)
O4—C13—C12120.2 (4)O10—C37—H37A109.6
O4—C13—C14119.3 (4)C38—C37—H37A109.6
C12—C13—C14120.5 (4)O10—C37—H37B109.6
C9—C14—C13116.3 (4)C38—C37—H37B109.6
C9—C14—C15121.8 (4)H37A—C37—H37B108.1
C13—C14—C15121.9 (4)C37—C38—N2115.0 (4)
O3—C15—C14121.7 (4)C37—C38—H38A108.5
O3—C15—C7122.6 (4)N2—C38—H38A108.5
C14—C15—C7115.6 (4)C37—C38—H38B108.5
O5—C16—C17109.9 (4)N2—C38—H38B108.5
O5—C16—H16A109.7H38A—C38—H38B107.5
C17—C16—H16A109.7C40—C39—N2114.0 (5)
O5—C16—H16B109.7C40—C39—H39A108.8
C17—C16—H16B109.7N2—C39—H39A108.8
H16A—C16—H16B108.2C40—C39—H39B108.8
N1—C17—C16114.6 (4)N2—C39—H39B108.8
N1—C17—H17A108.6H39A—C39—H39B107.7
C16—C17—H17A108.6C39—C40—H40A109.5
N1—C17—H17B108.6C39—C40—H40B109.5
C16—C17—H17B108.6H40A—C40—H40B109.5
H17A—C17—H17B107.6C39—C40—H40C109.5
C19—C18—N1114.4 (6)H40A—C40—H40C109.5
C19—C18—H18A108.7H40B—C40—H40C109.5
N1—C18—H18A108.7C42—C41—N2112.6 (5)
C19—C18—H18B108.7C42—C41—H41A109.1
N1—C18—H18B108.7N2—C41—H41A109.1
H18A—C18—H18B107.6C42—C41—H41B109.1
C18—C19—H19A109.5N2—C41—H41B109.1
C18—C19—H19B109.5H41A—C41—H41B107.8
H19A—C19—H19B109.5C41—C42—H42A109.5
C18—C19—H19C109.5C41—C42—H42B109.5
H19A—C19—H19C109.5H42A—C42—H42B109.5
H19B—C19—H19C109.5C41—C42—H42C109.5
C21—C20—N1112.9 (5)H42A—C42—H42C109.5
C21—C20—H20A109.0H42B—C42—H42C109.5
N1—C20—H20A109.0C17—N1—C20112.8 (4)
C21—C20—H20B109.0C17—N1—C18111.3 (4)
N1—C20—H20B109.0C20—N1—C18114.9 (4)
H20A—C20—H20B107.8C17—N1—H1B103 (4)
C20—C21—H21A109.5C20—N1—H1B106 (4)
C20—C21—H21B109.5C18—N1—H1B107 (3)
H21A—C21—H21B109.5C39—N2—C38111.4 (4)
C20—C21—H21C109.5C39—N2—C41111.4 (4)
H21A—C21—H21C109.5C38—N2—C41111.7 (4)
H21B—C21—H21C109.5C39—N2—H2B108 (4)
C23—C22—O6122.0 (5)C38—N2—H2B103 (4)
C23—C22—C27119.7 (5)C41—N2—H2B111 (4)
O6—C22—C27118.3 (5)C1—O1—H1109.5
C22—C23—C24119.9 (5)C8—O2—C9118.0 (4)
C22—C23—H23120.1C13—O4—H4109.5
C24—C23—H23120.1C11—O5—C16118.2 (4)
C23—C24—C25121.8 (5)C22—O6—H6A109.5
C23—C24—H24119.1C29—O7—C30118.1 (4)
C25—C24—H24119.1C34—O9—H9109.5
C26—C25—C24117.4 (4)C32—O10—C37117.3 (4)
O1—C1—C2—C3179.0 (5)C26—C25—C28—C3643.3 (7)
C6—C1—C2—C30.8 (8)C24—C25—C28—C36137.6 (5)
C1—C2—C3—C40.1 (8)C36—C28—C29—O71.7 (8)
C2—C3—C4—C51.1 (7)C25—C28—C29—O7176.2 (5)
C2—C3—C4—C7176.1 (4)O7—C30—C31—C32179.6 (4)
C3—C4—C5—C61.7 (7)C35—C30—C31—C320.1 (8)
C7—C4—C5—C6175.4 (4)C30—C31—C32—O10177.5 (4)
C4—C5—C6—C11.1 (7)C30—C31—C32—C330.4 (7)
O1—C1—C6—C5179.6 (5)O10—C32—C33—C34177.2 (4)
C2—C1—C6—C50.2 (7)C31—C32—C33—C340.8 (7)
C5—C4—C7—C8137.0 (5)C32—C33—C34—O9179.2 (4)
C3—C4—C7—C840.0 (7)C32—C33—C34—C350.8 (7)
C5—C4—C7—C1543.3 (6)C31—C30—C35—C340.0 (7)
C3—C4—C7—C15139.7 (5)O7—C30—C35—C34179.5 (4)
C15—C7—C8—O20.5 (7)C31—C30—C35—C36177.2 (5)
C4—C7—C8—O2179.8 (4)O7—C30—C35—C362.3 (7)
O2—C9—C10—C11179.1 (4)O9—C34—C35—C30179.6 (4)
C14—C9—C10—C110.4 (7)C33—C34—C35—C300.4 (7)
C9—C10—C11—O5177.1 (4)O9—C34—C35—C362.4 (7)
C9—C10—C11—C120.6 (7)C33—C34—C35—C36177.6 (4)
O5—C11—C12—C13177.0 (4)C30—C35—C36—O8179.5 (5)
C10—C11—C12—C130.8 (7)C34—C35—C36—O83.4 (7)
C11—C12—C13—O4178.3 (4)C30—C35—C36—C281.0 (7)
C11—C12—C13—C140.8 (7)C34—C35—C36—C28176.1 (4)
C10—C9—C14—C130.4 (7)C29—C28—C36—O8177.6 (5)
O2—C9—C14—C13179.1 (4)C25—C28—C36—O84.5 (7)
C10—C9—C14—C15178.9 (4)C29—C28—C36—C352.9 (7)
O2—C9—C14—C150.5 (6)C25—C28—C36—C35175.0 (4)
O4—C13—C14—C9178.6 (4)O10—C37—C38—N288.0 (5)
C12—C13—C14—C90.5 (6)C16—C17—N1—C2076.5 (6)
O4—C13—C14—C150.0 (6)C16—C17—N1—C18152.6 (5)
C12—C13—C14—C15179.1 (4)C21—C20—N1—C17167.3 (5)
C9—C14—C15—O3177.8 (4)C21—C20—N1—C1863.6 (7)
C13—C14—C15—O30.7 (7)C19—C18—N1—C1767.5 (7)
C9—C14—C15—C70.8 (6)C19—C18—N1—C2062.3 (7)
C13—C14—C15—C7179.3 (4)C40—C39—N2—C3863.7 (6)
C8—C7—C15—O3177.8 (4)C40—C39—N2—C41170.9 (5)
C4—C7—C15—O31.9 (7)C37—C38—N2—C39168.9 (4)
C8—C7—C15—C140.8 (6)C37—C38—N2—C4165.9 (6)
C4—C7—C15—C14179.5 (4)C42—C41—N2—C3970.1 (6)
O5—C16—C17—N177.2 (5)C42—C41—N2—C38164.6 (5)
O6—C22—C23—C24179.4 (5)C7—C8—O2—C90.1 (7)
C27—C22—C23—C241.0 (8)C10—C9—O2—C8179.4 (4)
C22—C23—C24—C251.0 (8)C14—C9—O2—C80.1 (6)
C23—C24—C25—C260.0 (7)C12—C11—O5—C16173.6 (4)
C23—C24—C25—C28179.1 (4)C10—C11—O5—C164.2 (6)
C24—C25—C26—C271.0 (7)C17—C16—O5—C11172.1 (4)
C28—C25—C26—C27180.0 (4)C28—C29—O7—C301.6 (7)
C23—C22—C27—C260.1 (8)C31—C30—O7—C29175.9 (4)
O6—C22—C27—C26179.6 (5)C35—C30—O7—C293.6 (7)
C25—C26—C27—C220.9 (7)C31—C32—O10—C376.6 (7)
C26—C25—C28—C29138.8 (5)C33—C32—O10—C37171.4 (4)
C24—C25—C28—C2940.3 (7)C38—C37—O10—C32172.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···Cl1i0.78 (5)2.36 (6)3.130 (5)175 (6)
N1—H1B···Cl2i0.96 (6)2.14 (6)3.101 (5)172 (5)
O4—H4···O30.821.842.566 (4)147
O9—H9···O80.821.862.591 (4)148
O6—H6A···Cl2ii0.822.253.064 (5)174
O1—H1···Cl1ii0.822.283.092 (4)174
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z.
 

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