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There are two independent mol­ecules in the asymmetric unit of the title compound, C30H26ClNO3. Both mol­ecules are linked through C—H...O hydrogen bonds into centrosymmetric dimers, providing stabilization.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806044266/rz2082sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806044266/rz2082Isup2.hkl
Contains datablock I

CCDC reference: 630221

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.045
  • wR factor = 0.127
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.86 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.33 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C34 - C60 .. 6.16 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C33 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C34
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 8 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 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

2-Anilino-3-benzoyl-4-(2-chlorophenyl)-7,7-dimethyl-7,8-dihydro- 4H-chromen-5(6H)-one top
Crystal data top
C30H26ClNO3Z = 8
Mr = 483.97F(000) = 2032
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4318 reflections
a = 19.982 (5) Åθ = 2.2–20.9°
b = 13.768 (4) ŵ = 0.18 mm1
c = 19.018 (5) ÅT = 293 K
β = 103.956 (3)°Block, colourless
V = 5078 (2) Å30.26 × 0.22 × 0.16 mm
Data collection top
Bruck APEX-II CCD area-detector
diffractometer
8974 independent reflections
Radiation source: fine-focus sealed tube5707 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2323
Tmin = 0.954, Tmax = 0.971k = 1216
27044 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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0571P)2 + 1.1067P]
where P = (Fo2 + 2Fc2)/3
8974 reflections(Δ/σ)max < 0.001
635 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.33 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
Cl10.16108 (4)0.48676 (5)0.33783 (4)0.0632 (2)
Cl20.26123 (4)0.99927 (5)0.34510 (4)0.0704 (2)
O10.18566 (9)0.28086 (13)0.55956 (11)0.0757 (6)
O20.07317 (8)0.49171 (12)0.33570 (10)0.0618 (5)
O30.11028 (8)0.59057 (10)0.46954 (8)0.0491 (4)
O40.34680 (11)0.79099 (14)0.56146 (11)0.0835 (7)
O50.49362 (10)0.99592 (11)0.32865 (10)0.0628 (5)
O60.37832 (8)1.09846 (10)0.46665 (8)0.0494 (4)
N10.00914 (9)0.62913 (13)0.39520 (10)0.0453 (5)
H10.03000.61170.36820.054*
N20.44114 (11)1.13389 (13)0.38790 (11)0.0557 (5)
H20.46781.11580.36090.067*
C10.15463 (11)0.52607 (17)0.51283 (12)0.0445 (6)
C20.21029 (12)0.57921 (18)0.56491 (13)0.0573 (7)
H2A0.19280.60170.60540.069*
H2B0.22370.63570.54110.069*
C30.27344 (12)0.51524 (18)0.59327 (13)0.0516 (6)
C40.24839 (14)0.4188 (2)0.61678 (14)0.0710 (8)
H4A0.28760.37540.63100.085*
H4B0.23050.43010.65920.085*
C50.19326 (12)0.36868 (19)0.55975 (13)0.0548 (6)
C60.14630 (11)0.43024 (16)0.50647 (11)0.0410 (5)
C70.08938 (10)0.38390 (15)0.44984 (11)0.0380 (5)
H70.06610.33820.47550.046*
C80.11686 (10)0.32383 (16)0.39484 (12)0.0409 (5)
C90.14557 (11)0.36239 (17)0.34220 (13)0.0489 (6)
C100.16461 (14)0.3041 (2)0.29016 (15)0.0680 (8)
H100.18340.33190.25470.082*
C110.15533 (15)0.2055 (2)0.29186 (17)0.0749 (8)
H110.16730.16630.25700.090*
C120.12867 (14)0.1648 (2)0.34445 (17)0.0716 (8)
H120.12300.09790.34570.086*
C130.11020 (12)0.22212 (18)0.39545 (14)0.0561 (6)
H130.09280.19310.43150.067*
C140.03558 (10)0.45911 (15)0.41478 (11)0.0374 (5)
C150.02856 (11)0.43178 (16)0.36739 (11)0.0421 (5)
C160.04389 (10)0.32614 (16)0.35319 (11)0.0396 (5)
C170.04122 (12)0.28566 (18)0.28733 (12)0.0511 (6)
H170.03000.32410.25160.061*
C180.05526 (14)0.18834 (19)0.27467 (13)0.0609 (7)
H180.05280.16150.23050.073*
C190.07280 (13)0.13068 (19)0.32590 (14)0.0595 (7)
H190.08220.06510.31670.071*
C200.07637 (13)0.17006 (19)0.39072 (14)0.0591 (7)
H200.08860.13140.42570.071*
C210.06176 (12)0.26747 (18)0.40450 (12)0.0505 (6)
H210.06400.29370.44890.061*
C220.05076 (11)0.55663 (16)0.42556 (11)0.0393 (5)
C230.02076 (11)0.73136 (15)0.40147 (11)0.0424 (5)
C240.03522 (13)0.78954 (18)0.40307 (14)0.0571 (7)
H240.07810.76170.40080.069*
C250.02730 (16)0.88888 (19)0.40812 (16)0.0740 (8)
H250.06500.92780.40940.089*
C260.03569 (17)0.93104 (19)0.41124 (15)0.0719 (8)
H260.04090.99810.41550.086*
C270.09066 (14)0.87363 (19)0.40802 (13)0.0593 (7)
H270.13310.90210.40900.071*
C280.08400 (12)0.77376 (17)0.40335 (12)0.0490 (6)
H280.12180.73530.40150.059*
C290.32235 (15)0.5651 (2)0.65735 (15)0.0795 (9)
H29A0.33530.62750.64250.119*
H29B0.36280.52590.67380.119*
H29C0.29960.57320.69600.119*
C300.31091 (14)0.4997 (2)0.53385 (16)0.0816 (9)
H30A0.27970.47250.49210.122*
H30B0.34880.45600.55060.122*
H30C0.32800.56080.52120.122*
C310.36073 (11)0.93959 (17)0.50701 (11)0.0432 (5)
C320.34230 (13)0.8791 (2)0.56289 (14)0.0608 (7)
C330.32230 (18)0.9316 (2)0.62474 (16)0.0851 (10)
H33A0.29250.88940.64450.102*
H33B0.36370.94290.66270.102*
C340.28592 (13)1.02768 (19)0.60494 (13)0.0571 (7)
C350.33010 (13)1.09086 (18)0.56797 (13)0.0573 (7)
H35A0.30281.14540.54460.069*
H35B0.36871.11650.60430.069*
C360.35672 (11)1.03551 (17)0.51290 (12)0.0447 (5)
C370.41547 (11)1.06284 (16)0.42125 (12)0.0436 (5)
C380.42576 (11)0.96485 (15)0.41206 (11)0.0385 (5)
C390.38778 (11)0.89118 (15)0.44835 (11)0.0403 (5)
H390.42230.84370.47250.048*
C400.33230 (11)0.83403 (16)0.39465 (13)0.0458 (6)
C410.33817 (13)0.73242 (18)0.39197 (16)0.0651 (7)
H410.37460.70200.42420.078*
C420.29244 (17)0.6770 (2)0.3439 (2)0.0902 (11)
H420.29830.61000.34340.108*
C430.23822 (17)0.7190 (2)0.2966 (2)0.0895 (10)
H430.20730.68080.26350.107*
C440.22907 (14)0.8184 (2)0.29774 (16)0.0758 (8)
H440.19170.84750.26600.091*
C450.27630 (12)0.87447 (18)0.34677 (13)0.0531 (6)
C460.46688 (11)0.93616 (16)0.36375 (12)0.0427 (5)
C470.47926 (10)0.83123 (15)0.35072 (11)0.0375 (5)
C480.50989 (11)0.76785 (17)0.40613 (13)0.0474 (6)
H480.52200.78970.45380.057*
C490.52237 (14)0.67245 (18)0.39050 (16)0.0625 (7)
H490.54340.63080.42780.075*
C500.50423 (16)0.6387 (2)0.32098 (17)0.0712 (8)
H500.51200.57410.31100.085*
C510.47461 (15)0.7005 (2)0.26624 (15)0.0685 (8)
H510.46220.67790.21880.082*
C520.46300 (13)0.79621 (18)0.28084 (13)0.0540 (6)
H520.44390.83790.24280.065*
C530.43014 (13)1.23568 (16)0.39120 (12)0.0452 (6)
C540.36506 (13)1.27462 (18)0.38047 (14)0.0595 (7)
H540.32671.23410.37190.071*
C550.35698 (15)1.3740 (2)0.38245 (15)0.0701 (8)
H550.31301.40020.37580.084*
C560.41274 (16)1.4342 (2)0.39405 (16)0.0732 (8)
H560.40681.50110.39500.088*
C570.47767 (15)1.39545 (18)0.40426 (16)0.0702 (8)
H570.51581.43630.41220.084*
C580.48664 (13)1.29583 (17)0.40275 (13)0.0535 (6)
H580.53071.26970.40950.064*
C590.2758 (2)1.0793 (2)0.67220 (18)0.1070 (13)
H59A0.24561.04170.69380.160*
H59B0.25591.14210.65910.160*
H59C0.31961.08660.70630.160*
C600.21569 (15)1.0131 (2)0.5532 (2)0.0930 (11)
H60A0.22140.98390.50920.140*
H60B0.19321.07480.54240.140*
H60C0.18810.97140.57530.140*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0737 (4)0.0486 (4)0.0748 (5)0.0008 (3)0.0326 (4)0.0139 (3)
Cl20.0671 (4)0.0594 (4)0.0775 (5)0.0156 (3)0.0034 (4)0.0039 (3)
O10.0676 (12)0.0505 (12)0.0920 (14)0.0047 (10)0.0140 (10)0.0271 (10)
O20.0465 (9)0.0481 (10)0.0778 (12)0.0065 (8)0.0106 (9)0.0055 (9)
O30.0474 (9)0.0361 (9)0.0562 (10)0.0057 (7)0.0027 (8)0.0033 (7)
O40.1155 (17)0.0527 (12)0.1050 (16)0.0246 (12)0.0711 (14)0.0341 (11)
O50.0867 (13)0.0393 (10)0.0799 (12)0.0013 (9)0.0543 (11)0.0071 (8)
O60.0685 (10)0.0328 (8)0.0561 (10)0.0031 (8)0.0331 (8)0.0033 (7)
N10.0417 (10)0.0368 (11)0.0523 (11)0.0061 (9)0.0011 (9)0.0015 (9)
N20.0742 (14)0.0339 (11)0.0736 (14)0.0046 (10)0.0461 (12)0.0001 (10)
C10.0389 (12)0.0450 (14)0.0471 (13)0.0063 (11)0.0055 (10)0.0008 (11)
C20.0513 (14)0.0541 (16)0.0594 (15)0.0000 (12)0.0006 (12)0.0075 (12)
C30.0416 (13)0.0553 (16)0.0523 (14)0.0003 (12)0.0003 (11)0.0030 (12)
C40.0635 (17)0.073 (2)0.0623 (17)0.0043 (15)0.0120 (14)0.0172 (15)
C50.0473 (14)0.0529 (17)0.0596 (16)0.0008 (13)0.0037 (12)0.0167 (13)
C60.0374 (12)0.0411 (14)0.0435 (13)0.0008 (10)0.0077 (10)0.0046 (10)
C70.0369 (11)0.0345 (12)0.0424 (12)0.0015 (10)0.0092 (10)0.0041 (10)
C80.0338 (11)0.0381 (13)0.0496 (13)0.0041 (10)0.0074 (10)0.0055 (10)
C90.0463 (13)0.0446 (14)0.0571 (15)0.0040 (11)0.0152 (12)0.0045 (12)
C100.0713 (18)0.070 (2)0.0722 (19)0.0088 (16)0.0360 (15)0.0024 (15)
C110.079 (2)0.065 (2)0.090 (2)0.0135 (16)0.0389 (18)0.0131 (16)
C120.0709 (18)0.0409 (16)0.109 (2)0.0081 (14)0.0329 (17)0.0054 (16)
C130.0482 (14)0.0471 (16)0.0748 (18)0.0060 (12)0.0180 (13)0.0033 (13)
C140.0372 (12)0.0357 (12)0.0389 (12)0.0029 (10)0.0082 (9)0.0001 (9)
C150.0408 (12)0.0432 (13)0.0415 (12)0.0018 (11)0.0081 (10)0.0020 (10)
C160.0319 (11)0.0432 (13)0.0408 (12)0.0009 (10)0.0032 (9)0.0024 (10)
C170.0628 (15)0.0507 (16)0.0396 (13)0.0048 (12)0.0120 (11)0.0030 (11)
C180.0795 (19)0.0567 (17)0.0445 (14)0.0030 (14)0.0112 (13)0.0080 (13)
C190.0730 (17)0.0417 (14)0.0552 (16)0.0071 (13)0.0014 (13)0.0009 (12)
C200.0667 (17)0.0566 (17)0.0527 (16)0.0126 (14)0.0121 (13)0.0111 (13)
C210.0524 (14)0.0568 (16)0.0430 (14)0.0019 (12)0.0129 (11)0.0011 (12)
C220.0363 (12)0.0421 (13)0.0388 (12)0.0041 (11)0.0075 (10)0.0014 (10)
C230.0507 (14)0.0367 (13)0.0392 (13)0.0058 (11)0.0099 (10)0.0047 (10)
C240.0572 (15)0.0465 (15)0.0714 (17)0.0119 (13)0.0228 (13)0.0170 (12)
C250.083 (2)0.0429 (16)0.107 (2)0.0206 (15)0.0424 (18)0.0183 (15)
C260.096 (2)0.0347 (15)0.088 (2)0.0002 (16)0.0279 (18)0.0035 (14)
C270.0665 (17)0.0520 (17)0.0590 (16)0.0087 (14)0.0145 (13)0.0060 (13)
C280.0507 (14)0.0478 (15)0.0488 (14)0.0042 (12)0.0126 (11)0.0021 (11)
C290.0669 (18)0.080 (2)0.0751 (19)0.0082 (16)0.0151 (15)0.0013 (16)
C300.0520 (16)0.107 (3)0.086 (2)0.0012 (16)0.0181 (15)0.0032 (18)
C310.0457 (13)0.0426 (14)0.0454 (13)0.0021 (11)0.0186 (10)0.0062 (10)
C320.0677 (17)0.0554 (18)0.0685 (18)0.0160 (14)0.0343 (14)0.0217 (14)
C330.114 (3)0.085 (2)0.075 (2)0.030 (2)0.0583 (19)0.0287 (17)
C340.0610 (16)0.0594 (17)0.0606 (16)0.0091 (13)0.0338 (13)0.0041 (13)
C350.0632 (16)0.0590 (16)0.0570 (15)0.0009 (13)0.0287 (13)0.0086 (12)
C360.0474 (13)0.0444 (15)0.0453 (13)0.0009 (11)0.0172 (11)0.0003 (11)
C370.0496 (13)0.0384 (13)0.0474 (13)0.0021 (11)0.0205 (11)0.0032 (11)
C380.0432 (12)0.0309 (12)0.0441 (13)0.0027 (10)0.0154 (10)0.0008 (9)
C390.0416 (12)0.0320 (12)0.0497 (13)0.0006 (10)0.0160 (10)0.0045 (10)
C400.0442 (13)0.0372 (13)0.0620 (15)0.0034 (11)0.0243 (12)0.0009 (11)
C410.0514 (15)0.0441 (16)0.103 (2)0.0104 (13)0.0248 (15)0.0047 (14)
C420.066 (2)0.0514 (19)0.155 (3)0.0193 (17)0.030 (2)0.026 (2)
C430.070 (2)0.075 (2)0.121 (3)0.0296 (19)0.019 (2)0.038 (2)
C440.0530 (16)0.087 (2)0.085 (2)0.0111 (16)0.0109 (15)0.0094 (17)
C450.0468 (14)0.0504 (15)0.0647 (16)0.0019 (12)0.0184 (13)0.0028 (12)
C460.0465 (13)0.0360 (13)0.0475 (13)0.0005 (11)0.0153 (11)0.0030 (10)
C470.0367 (12)0.0360 (12)0.0424 (13)0.0006 (10)0.0149 (10)0.0009 (10)
C480.0451 (13)0.0486 (15)0.0472 (14)0.0054 (11)0.0088 (11)0.0034 (11)
C490.0690 (17)0.0479 (16)0.0749 (19)0.0202 (14)0.0259 (14)0.0191 (14)
C500.100 (2)0.0428 (16)0.085 (2)0.0117 (15)0.0507 (18)0.0038 (15)
C510.096 (2)0.0563 (18)0.0586 (17)0.0004 (16)0.0301 (16)0.0132 (14)
C520.0687 (16)0.0513 (16)0.0428 (14)0.0119 (13)0.0147 (12)0.0036 (11)
C530.0636 (15)0.0316 (13)0.0466 (13)0.0004 (11)0.0256 (12)0.0021 (10)
C540.0583 (16)0.0473 (16)0.0753 (18)0.0022 (13)0.0206 (14)0.0053 (13)
C550.0661 (18)0.0563 (18)0.091 (2)0.0155 (15)0.0257 (16)0.0102 (15)
C560.091 (2)0.0352 (15)0.099 (2)0.0119 (16)0.0349 (18)0.0062 (14)
C570.077 (2)0.0391 (15)0.095 (2)0.0107 (14)0.0227 (16)0.0020 (14)
C580.0559 (15)0.0382 (14)0.0706 (17)0.0009 (12)0.0233 (13)0.0052 (12)
C590.164 (4)0.097 (3)0.089 (2)0.030 (2)0.086 (2)0.0105 (19)
C600.0580 (18)0.086 (2)0.143 (3)0.0003 (17)0.040 (2)0.009 (2)
Geometric parameters (Å, º) top
Cl1—C91.746 (2)C27—H270.9300
Cl2—C451.743 (3)C28—H280.9300
O1—C51.219 (3)C29—H29A0.9600
O2—C151.257 (3)C29—H29B0.9600
O3—C221.361 (2)C29—H29C0.9600
O3—C11.378 (3)C30—H30A0.9600
O4—C321.217 (3)C30—H30B0.9600
O5—C461.257 (2)C30—H30C0.9600
O6—C371.359 (2)C31—C361.329 (3)
O6—C361.376 (3)C31—C321.465 (3)
N1—C221.338 (3)C31—C391.507 (3)
N1—C231.427 (3)C32—C331.514 (4)
N1—H10.8600C33—C341.513 (4)
N2—C371.334 (3)C33—H33A0.9700
N2—C531.422 (3)C33—H33B0.9700
N2—H20.8600C34—C591.519 (4)
C1—C61.332 (3)C34—C601.520 (4)
C1—C21.491 (3)C34—C351.526 (3)
C2—C31.527 (3)C35—C361.493 (3)
C2—H2A0.9700C35—H35A0.9700
C2—H2B0.9700C35—H35B0.9700
C3—C301.514 (4)C37—C381.382 (3)
C3—C41.523 (3)C38—C461.428 (3)
C3—C291.529 (3)C38—C391.528 (3)
C4—C51.513 (3)C39—C401.531 (3)
C4—H4A0.9700C39—H390.9800
C4—H4B0.9700C40—C451.378 (3)
C5—C61.472 (3)C40—C411.406 (3)
C6—C71.507 (3)C41—C421.361 (4)
C7—C141.525 (3)C41—H410.9300
C7—C81.535 (3)C42—C431.359 (4)
C7—H70.9800C42—H420.9300
C8—C91.375 (3)C43—C441.382 (4)
C8—C131.407 (3)C43—H430.9300
C9—C101.396 (3)C44—C451.390 (4)
C10—C111.371 (4)C44—H440.9300
C10—H100.9300C46—C471.496 (3)
C11—C121.362 (4)C47—C521.377 (3)
C11—H110.9300C47—C481.391 (3)
C12—C131.368 (4)C48—C491.383 (3)
C12—H120.9300C48—H480.9300
C13—H130.9300C49—C501.365 (4)
C14—C221.381 (3)C49—H490.9300
C14—C151.428 (3)C50—C511.364 (4)
C15—C161.497 (3)C50—H500.9300
C16—C211.378 (3)C51—C521.378 (3)
C16—C171.384 (3)C51—H510.9300
C17—C181.378 (3)C52—H520.9300
C17—H170.9300C53—C581.374 (3)
C18—C191.366 (3)C53—C541.376 (3)
C18—H180.9300C54—C551.380 (3)
C19—C201.364 (3)C54—H540.9300
C19—H190.9300C55—C561.363 (4)
C20—C211.384 (3)C55—H550.9300
C20—H200.9300C56—C571.373 (4)
C21—H210.9300C56—H560.9300
C23—C241.382 (3)C57—C581.384 (3)
C23—C281.384 (3)C57—H570.9300
C24—C251.378 (3)C58—H580.9300
C24—H240.9300C59—H59A0.9600
C25—C261.374 (4)C59—H59B0.9600
C25—H250.9300C59—H59C0.9600
C26—C271.367 (4)C60—H60A0.9600
C26—H260.9300C60—H60B0.9600
C27—C281.382 (3)C60—H60C0.9600
C22—O3—C1119.11 (17)H30A—C30—H30B109.5
C37—O6—C36118.84 (17)C3—C30—H30C109.5
C22—N1—C23128.92 (19)H30A—C30—H30C109.5
C22—N1—H1115.5H30B—C30—H30C109.5
C23—N1—H1115.5C36—C31—C32118.2 (2)
C37—N2—C53128.33 (19)C36—C31—C39122.77 (19)
C37—N2—H2115.8C32—C31—C39118.9 (2)
C53—N2—H2115.8O4—C32—C31121.2 (2)
C6—C1—O3122.4 (2)O4—C32—C33121.8 (2)
C6—C1—C2127.1 (2)C31—C32—C33116.9 (2)
O3—C1—C2110.48 (19)C34—C33—C32115.1 (2)
C1—C2—C3111.9 (2)C34—C33—H33A108.5
C1—C2—H2A109.2C32—C33—H33A108.5
C3—C2—H2A109.2C34—C33—H33B108.5
C1—C2—H2B109.2C32—C33—H33B108.5
C3—C2—H2B109.2H33A—C33—H33B107.5
H2A—C2—H2B107.9C33—C34—C59110.7 (2)
C30—C3—C4110.6 (2)C33—C34—C60111.0 (3)
C30—C3—C2109.5 (2)C59—C34—C60108.5 (2)
C4—C3—C2107.7 (2)C33—C34—C35108.4 (2)
C30—C3—C29108.8 (2)C59—C34—C35109.3 (2)
C4—C3—C29110.5 (2)C60—C34—C35108.9 (2)
C2—C3—C29109.7 (2)C36—C35—C34112.1 (2)
C5—C4—C3114.9 (2)C36—C35—H35A109.2
C5—C4—H4A108.5C34—C35—H35A109.2
C3—C4—H4A108.5C36—C35—H35B109.2
C5—C4—H4B108.5C34—C35—H35B109.2
C3—C4—H4B108.5H35A—C35—H35B107.9
H4A—C4—H4B107.5C31—C36—O6122.49 (19)
O1—C5—C6120.7 (2)C31—C36—C35127.2 (2)
O1—C5—C4121.6 (2)O6—C36—C35110.28 (19)
C6—C5—C4117.6 (2)N2—C37—O6111.66 (19)
C1—C6—C5117.6 (2)N2—C37—C38124.7 (2)
C1—C6—C7122.73 (19)O6—C37—C38123.61 (19)
C5—C6—C7119.6 (2)C37—C38—C46118.54 (19)
C6—C7—C14110.85 (17)C37—C38—C39119.05 (18)
C6—C7—C8112.51 (17)C46—C38—C39122.18 (18)
C14—C7—C8113.46 (17)C31—C39—C38110.28 (17)
C6—C7—H7106.5C31—C39—C40112.94 (17)
C14—C7—H7106.5C38—C39—C40113.48 (17)
C8—C7—H7106.5C31—C39—H39106.5
C9—C8—C13116.6 (2)C38—C39—H39106.5
C9—C8—C7124.7 (2)C40—C39—H39106.5
C13—C8—C7118.71 (19)C45—C40—C41116.1 (2)
C8—C9—C10121.8 (2)C45—C40—C39125.1 (2)
C8—C9—Cl1121.57 (18)C41—C40—C39118.8 (2)
C10—C9—Cl1116.61 (19)C42—C41—C40122.3 (3)
C11—C10—C9119.4 (3)C42—C41—H41118.9
C11—C10—H10120.3C40—C41—H41118.9
C9—C10—H10120.3C43—C42—C41120.4 (3)
C12—C11—C10120.2 (3)C43—C42—H42119.8
C12—C11—H11119.9C41—C42—H42119.8
C10—C11—H11119.9C42—C43—C44119.9 (3)
C11—C12—C13120.2 (3)C42—C43—H43120.1
C11—C12—H12119.9C44—C43—H43120.1
C13—C12—H12119.9C43—C44—C45119.3 (3)
C12—C13—C8121.7 (2)C43—C44—H44120.3
C12—C13—H13119.1C45—C44—H44120.3
C8—C13—H13119.1C40—C45—C44122.0 (3)
C22—C14—C15118.79 (19)C40—C45—Cl2121.29 (19)
C22—C14—C7119.26 (18)C44—C45—Cl2116.7 (2)
C15—C14—C7121.84 (19)O5—C46—C38123.0 (2)
O2—C15—C14123.7 (2)O5—C46—C47115.81 (19)
O2—C15—C16117.43 (19)C38—C46—C47121.16 (19)
C14—C15—C16118.89 (19)C52—C47—C48118.0 (2)
C21—C16—C17118.5 (2)C52—C47—C46119.20 (19)
C21—C16—C15121.2 (2)C48—C47—C46122.7 (2)
C17—C16—C15120.24 (19)C49—C48—C47120.1 (2)
C18—C17—C16119.9 (2)C49—C48—H48119.9
C18—C17—H17120.0C47—C48—H48119.9
C16—C17—H17120.0C50—C49—C48120.8 (2)
C19—C18—C17121.1 (2)C50—C49—H49119.6
C19—C18—H18119.4C48—C49—H49119.6
C17—C18—H18119.4C49—C50—C51119.5 (3)
C20—C19—C18119.4 (2)C49—C50—H50120.3
C20—C19—H19120.3C51—C50—H50120.3
C18—C19—H19120.3C50—C51—C52120.4 (3)
C19—C20—C21120.1 (2)C50—C51—H51119.8
C19—C20—H20119.9C52—C51—H51119.8
C21—C20—H20119.9C47—C52—C51121.2 (2)
C16—C21—C20120.8 (2)C47—C52—H52119.4
C16—C21—H21119.6C51—C52—H52119.4
C20—C21—H21119.6C58—C53—C54120.0 (2)
N1—C22—O3111.66 (18)C58—C53—N2118.1 (2)
N1—C22—C14124.74 (19)C54—C53—N2121.9 (2)
O3—C22—C14123.59 (18)C53—C54—C55119.7 (2)
C24—C23—C28119.6 (2)C53—C54—H54120.2
C24—C23—N1117.2 (2)C55—C54—H54120.2
C28—C23—N1123.2 (2)C56—C55—C54120.7 (3)
C25—C24—C23119.8 (2)C56—C55—H55119.6
C25—C24—H24120.1C54—C55—H55119.6
C23—C24—H24120.1C55—C56—C57119.6 (3)
C24—C25—C26120.7 (3)C55—C56—H56120.2
C24—C25—H25119.6C57—C56—H56120.2
C26—C25—H25119.6C56—C57—C58120.3 (3)
C27—C26—C25119.4 (2)C56—C57—H57119.8
C27—C26—H26120.3C58—C57—H57119.8
C25—C26—H26120.3C53—C58—C57119.7 (2)
C26—C27—C28120.8 (3)C53—C58—H58120.2
C26—C27—H27119.6C57—C58—H58120.2
C28—C27—H27119.6C34—C59—H59A109.5
C27—C28—C23119.6 (2)C34—C59—H59B109.5
C27—C28—H28120.2H59A—C59—H59B109.5
C23—C28—H28120.2C34—C59—H59C109.5
C3—C29—H29A109.5H59A—C59—H59C109.5
C3—C29—H29B109.5H59B—C59—H59C109.5
H29A—C29—H29B109.5C34—C60—H60A109.5
C3—C29—H29C109.5C34—C60—H60B109.5
H29A—C29—H29C109.5H60A—C60—H60B109.5
H29B—C29—H29C109.5C34—C60—H60C109.5
C3—C30—H30A109.5H60A—C60—H60C109.5
C3—C30—H30B109.5H60B—C60—H60C109.5
C22—O3—C1—C69.2 (3)C36—C31—C32—O4177.9 (3)
C22—O3—C1—C2170.82 (19)C39—C31—C32—O41.9 (4)
C6—C1—C2—C321.3 (3)C36—C31—C32—C332.0 (4)
O3—C1—C2—C3158.70 (19)C39—C31—C32—C33174.0 (2)
C1—C2—C3—C3072.4 (3)O4—C32—C33—C34151.4 (3)
C1—C2—C3—C448.0 (3)C31—C32—C33—C3432.7 (4)
C1—C2—C3—C29168.3 (2)C32—C33—C34—C59173.4 (3)
C30—C3—C4—C566.2 (3)C32—C33—C34—C6066.1 (3)
C2—C3—C4—C553.4 (3)C32—C33—C34—C3553.5 (4)
C29—C3—C4—C5173.2 (2)C33—C34—C35—C3645.0 (3)
C3—C4—C5—O1153.7 (3)C59—C34—C35—C36165.7 (2)
C3—C4—C5—C629.6 (3)C60—C34—C35—C3675.9 (3)
O3—C1—C6—C5174.8 (2)C32—C31—C36—O6174.5 (2)
C2—C1—C6—C55.3 (4)C39—C31—C36—O61.4 (3)
O3—C1—C6—C72.3 (3)C32—C31—C36—C355.0 (4)
C2—C1—C6—C7177.7 (2)C39—C31—C36—C35179.2 (2)
O1—C5—C6—C1175.5 (2)C37—O6—C36—C3111.3 (3)
C4—C5—C6—C11.2 (3)C37—O6—C36—C35168.24 (19)
O1—C5—C6—C71.6 (4)C34—C35—C36—C3118.1 (4)
C4—C5—C6—C7178.4 (2)C34—C35—C36—O6162.4 (2)
C1—C6—C7—C1413.0 (3)C53—N2—C37—O64.5 (3)
C5—C6—C7—C14163.98 (19)C53—N2—C37—C38176.3 (2)
C1—C6—C7—C8115.2 (2)C36—O6—C37—N2170.73 (19)
C5—C6—C7—C867.8 (3)C36—O6—C37—C388.4 (3)
C6—C7—C8—C971.9 (3)N2—C37—C38—C460.2 (3)
C14—C7—C8—C955.0 (3)O6—C37—C38—C46178.9 (2)
C6—C7—C8—C13110.8 (2)N2—C37—C38—C39174.4 (2)
C14—C7—C8—C13122.3 (2)O6—C37—C38—C396.6 (3)
C13—C8—C9—C102.5 (3)C36—C31—C39—C3814.8 (3)
C7—C8—C9—C10174.8 (2)C32—C31—C39—C38161.0 (2)
C13—C8—C9—Cl1176.65 (17)C36—C31—C39—C40113.4 (2)
C7—C8—C9—Cl16.0 (3)C32—C31—C39—C4070.8 (3)
C8—C9—C10—C110.8 (4)C37—C38—C39—C3116.9 (3)
Cl1—C9—C10—C11178.4 (2)C46—C38—C39—C31168.71 (19)
C9—C10—C11—C120.9 (4)C37—C38—C39—C40110.9 (2)
C10—C11—C12—C130.8 (5)C46—C38—C39—C4063.4 (3)
C11—C12—C13—C81.1 (4)C31—C39—C40—C4567.2 (3)
C9—C8—C13—C122.6 (3)C38—C39—C40—C4559.3 (3)
C7—C8—C13—C12174.9 (2)C31—C39—C40—C41113.9 (2)
C6—C7—C14—C2213.5 (3)C38—C39—C40—C41119.6 (2)
C8—C7—C14—C22114.2 (2)C45—C40—C41—C421.6 (4)
C6—C7—C14—C15170.45 (18)C39—C40—C41—C42177.5 (2)
C8—C7—C14—C1561.8 (3)C40—C41—C42—C430.7 (5)
C22—C14—C15—O21.6 (3)C41—C42—C43—C440.6 (5)
C7—C14—C15—O2177.6 (2)C42—C43—C44—C451.0 (5)
C22—C14—C15—C16177.49 (19)C41—C40—C45—C441.2 (4)
C7—C14—C15—C161.4 (3)C39—C40—C45—C44177.8 (2)
O2—C15—C16—C21106.1 (2)C41—C40—C45—Cl2178.65 (18)
C14—C15—C16—C2174.8 (3)C39—C40—C45—Cl22.4 (3)
O2—C15—C16—C1773.0 (3)C43—C44—C45—C400.1 (4)
C14—C15—C16—C17106.1 (2)C43—C44—C45—Cl2179.9 (2)
C21—C16—C17—C181.0 (3)C37—C38—C46—O50.7 (3)
C15—C16—C17—C18179.9 (2)C39—C38—C46—O5173.7 (2)
C16—C17—C18—C190.9 (4)C37—C38—C46—C47179.2 (2)
C17—C18—C19—C200.1 (4)C39—C38—C46—C474.8 (3)
C18—C19—C20—C210.5 (4)O5—C46—C47—C5253.8 (3)
C17—C16—C21—C200.3 (3)C38—C46—C47—C52124.9 (2)
C15—C16—C21—C20179.5 (2)O5—C46—C47—C48122.9 (2)
C19—C20—C21—C160.4 (4)C38—C46—C47—C4858.4 (3)
C23—N1—C22—O32.4 (3)C52—C47—C48—C490.8 (3)
C23—N1—C22—C14178.3 (2)C46—C47—C48—C49177.6 (2)
C1—O3—C22—N1171.06 (18)C47—C48—C49—C500.8 (4)
C1—O3—C22—C148.3 (3)C48—C49—C50—C511.2 (4)
C15—C14—C22—N10.7 (3)C49—C50—C51—C520.0 (4)
C7—C14—C22—N1176.91 (19)C48—C47—C52—C512.0 (3)
C15—C14—C22—O3179.97 (19)C46—C47—C52—C51178.9 (2)
C7—C14—C22—O33.9 (3)C50—C51—C52—C471.6 (4)
C22—N1—C23—C24143.7 (2)C37—N2—C53—C58132.7 (3)
C22—N1—C23—C2838.6 (3)C37—N2—C53—C5449.9 (4)
C28—C23—C24—C251.4 (4)C58—C53—C54—C551.0 (4)
N1—C23—C24—C25179.2 (2)N2—C53—C54—C55178.4 (2)
C23—C24—C25—C260.3 (4)C53—C54—C55—C560.8 (4)
C24—C25—C26—C271.1 (5)C54—C55—C56—C570.3 (5)
C25—C26—C27—C281.5 (4)C55—C56—C57—C580.1 (5)
C26—C27—C28—C230.4 (4)C54—C53—C58—C570.7 (4)
C24—C23—C28—C271.1 (3)N2—C53—C58—C57178.2 (2)
N1—C23—C28—C27178.7 (2)C56—C57—C58—C530.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21—H21···O3i0.932.553.409 (3)154
C24—H24···O1i0.932.513.393 (3)158
N1—H1···O20.861.902.582 (2)136
N2—H2···O50.861.882.559 (2)135
C28—H28···O30.932.422.811 (3)106
C58—H58···O4ii0.932.523.446 (3)175
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+2, z+1.
 

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