# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013


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#                                CCDC 
# 
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#  This CIF contains data from an original supplementary publication 
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#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
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data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 911557'
#TrackingRef 'shelxl.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H9 Cl O2'
_chemical_formula_weight         256.67
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   9.6658(12)
_cell_length_b                   10.3292(14)
_cell_length_c                   18.5201(18)
_cell_angle_alpha                85.614(12)
_cell_angle_beta                 86.144(14)
_cell_angle_gamma                81.723(10)
_cell_volume                     1821.5(4)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9418
_exptl_absorpt_correction_T_max  0.9645
_exptl_absorpt_process_details   CrystalClear
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn 70'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18731
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0965
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         27.86
_reflns_number_total             8534
_reflns_number_gt                3529
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0205(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         8534
_refine_ls_number_parameters     488
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   0.848
_refine_ls_restrained_S_all      0.848
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.33649(6) -0.17283(6) 0.20692(3) 0.0666(2) Uani 1 1 d . . .
Cl2 Cl 0.61654(7) 1.21914(6) 1.06744(3) 0.0703(2) Uani 1 1 d . . .
Cl3 Cl 0.02915(7) 1.19227(7) 0.85379(4) 0.0801(2) Uani 1 1 d . . .
O1 O -0.04154(14) -0.11075(13) 0.40488(7) 0.0487(4) Uani 1 1 d . . .
O2 O -0.22359(16) -0.10513(14) 0.48211(9) 0.0666(5) Uani 1 1 d . . .
O3 O 0.58124(16) 0.73759(15) 1.09184(8) 0.0593(4) Uani 1 1 d . . .
O4 O 0.53530(19) 0.53357(17) 1.10480(9) 0.0865(6) Uani 1 1 d . . .
O5 O 0.42034(16) 1.19336(14) 0.66252(8) 0.0575(4) Uani 1 1 d . . .
O6 O 0.58186(17) 1.21606(16) 0.57453(9) 0.0715(5) Uani 1 1 d . . .
C1 C 0.0465(2) -0.04848(19) 0.35695(10) 0.0393(5) Uani 1 1 d . . .
C2 C 0.1363(2) -0.1294(2) 0.31358(11) 0.0457(5) Uani 1 1 d . . .
H2 H 0.1387 -0.2200 0.3191 0.055 Uiso 1 1 calc R . .
C3 C 0.2218(2) -0.0732(2) 0.26217(11) 0.0455(5) Uani 1 1 d . . .
C4 C 0.2178(2) 0.0619(2) 0.25355(11) 0.0511(6) Uani 1 1 d . . .
H4 H 0.2747 0.0992 0.2177 0.061 Uiso 1 1 calc R . .
C5 C 0.1292(2) 0.1402(2) 0.29835(11) 0.0459(5) Uani 1 1 d . . .
H5 H 0.1274 0.2306 0.2926 0.055 Uiso 1 1 calc R . .
C6 C 0.0414(2) 0.08708(19) 0.35251(10) 0.0381(5) Uani 1 1 d . . .
C7 C -0.0589(2) 0.16272(18) 0.40054(10) 0.0385(5) Uani 1 1 d . . .
C8 C -0.1472(2) 0.09879(19) 0.44463(11) 0.0436(5) Uani 1 1 d . . .
H8 H -0.2124 0.1472 0.4749 0.052 Uiso 1 1 calc R . .
C9 C -0.1450(2) -0.0417(2) 0.44692(12) 0.0465(5) Uani 1 1 d . . .
C10 C -0.0690(2) 0.30700(19) 0.40021(10) 0.0408(5) Uani 1 1 d . . .
C11 C 0.0476(2) 0.3696(2) 0.40664(11) 0.0495(6) Uani 1 1 d . . .
H11 H 0.1359 0.3209 0.4099 0.059 Uiso 1 1 calc R . .
C12 C 0.0313(3) 0.5045(2) 0.40816(13) 0.0597(7) Uani 1 1 d . . .
H12 H 0.1091 0.5462 0.4125 0.072 Uiso 1 1 calc R . .
C13 C -0.0988(3) 0.5780(2) 0.40327(12) 0.0604(7) Uani 1 1 d . . .
H13 H -0.1085 0.6688 0.4040 0.073 Uiso 1 1 calc R . .
C14 C -0.2145(2) 0.5167(2) 0.39728(12) 0.0581(6) Uani 1 1 d . . .
H14 H -0.3026 0.5660 0.3943 0.070 Uiso 1 1 calc R . .
C15 C -0.1997(2) 0.3826(2) 0.39570(11) 0.0502(6) Uani 1 1 d . . .
H15 H -0.2783 0.3419 0.3916 0.060 Uiso 1 1 calc R . .
C16 C 0.6448(2) 0.8344(2) 1.05339(11) 0.0473(6) Uani 1 1 d . . .
C17 C 0.6071(2) 0.9594(2) 1.07708(12) 0.0510(6) Uani 1 1 d . . .
H17 H 0.5443 0.9739 1.1169 0.061 Uiso 1 1 calc R . .
C18 C 0.6644(2) 1.0609(2) 1.04042(12) 0.0509(6) Uani 1 1 d . . .
C19 C 0.7576(2) 1.0396(2) 0.98060(12) 0.0606(7) Uani 1 1 d . . .
H19 H 0.7956 1.1092 0.9559 0.073 Uiso 1 1 calc R . .
C20 C 0.7929(2) 0.9151(2) 0.95844(12) 0.0577(6) Uani 1 1 d . . .
H20 H 0.8548 0.9015 0.9182 0.069 Uiso 1 1 calc R . .
C21 C 0.7384(2) 0.8073(2) 0.99458(11) 0.0454(5) Uani 1 1 d . . .
C22 C 0.7678(2) 0.6737(2) 0.97336(11) 0.0485(6) Uani 1 1 d . . .
C23 C 0.6986(2) 0.5823(2) 1.01029(12) 0.0571(6) Uani 1 1 d . . .
H23 H 0.7158 0.4968 0.9960 0.069 Uiso 1 1 calc R . .
C24 C 0.6000(3) 0.6104(2) 1.07044(13) 0.0613(7) Uani 1 1 d . . .
C25 C 0.8676(2) 0.6356(2) 0.91182(12) 0.0514(6) Uani 1 1 d . . .
C26 C 1.0054(3) 0.6597(2) 0.90891(13) 0.0634(7) Uani 1 1 d . . .
H26 H 1.0362 0.7037 0.9454 0.076 Uiso 1 1 calc R . .
C27 C 1.0976(3) 0.6186(3) 0.85191(15) 0.0736(8) Uani 1 1 d . . .
H27 H 1.1902 0.6341 0.8504 0.088 Uiso 1 1 calc R . .
C28 C 1.0513(3) 0.5548(2) 0.79754(15) 0.0777(9) Uani 1 1 d . . .
H28 H 1.1129 0.5273 0.7592 0.093 Uiso 1 1 calc R . .
C29 C 0.9152(3) 0.5315(2) 0.79962(14) 0.0756(8) Uani 1 1 d . . .
H29 H 0.8845 0.4892 0.7624 0.091 Uiso 1 1 calc R . .
C30 C 0.8232(3) 0.5707(2) 0.85674(13) 0.0616(7) Uani 1 1 d . . .
H30 H 0.7312 0.5534 0.8582 0.074 Uiso 1 1 calc R . .
C31 C 0.3395(2) 1.1159(2) 0.70644(12) 0.0483(6) Uani 1 1 d . . .
C32 C 0.2405(2) 1.1826(2) 0.75178(12) 0.0561(6) Uani 1 1 d . . .
H32 H 0.2330 1.2731 0.7534 0.067 Uiso 1 1 calc R . .
C33 C 0.1531(2) 1.1118(2) 0.79458(12) 0.0543(6) Uani 1 1 d . . .
C34 C 0.1615(2) 0.9776(2) 0.79119(12) 0.0567(6) Uani 1 1 d . . .
H34 H 0.0984 0.9315 0.8189 0.068 Uiso 1 1 calc R . .
C35 C 0.2632(2) 0.9128(2) 0.74675(11) 0.0494(6) Uani 1 1 d . . .
H35 H 0.2687 0.8225 0.7449 0.059 Uiso 1 1 calc R . .
C36 C 0.3596(2) 0.9799(2) 0.70384(11) 0.0434(5) Uani 1 1 d . . .
C37 C 0.4731(2) 0.9193(2) 0.65643(11) 0.0432(5) Uani 1 1 d . . .
C38 C 0.5456(2) 0.9991(2) 0.61268(11) 0.0514(6) Uani 1 1 d . . .
H38 H 0.6155 0.9612 0.5807 0.062 Uiso 1 1 calc R . .
C39 C 0.5209(3) 1.1398(2) 0.61265(13) 0.0549(6) Uani 1 1 d . . .
C40 C 0.5104(2) 0.7757(2) 0.65615(12) 0.0438(5) Uani 1 1 d . . .
C41 C 0.5170(2) 0.6949(2) 0.71982(12) 0.0523(6) Uani 1 1 d . . .
H41 H 0.4972 0.7315 0.7643 0.063 Uiso 1 1 calc R . .
C42 C 0.5528(2) 0.5606(2) 0.71760(14) 0.0616(7) Uani 1 1 d . . .
H42 H 0.5565 0.5079 0.7606 0.074 Uiso 1 1 calc R . .
C43 C 0.5828(2) 0.5045(2) 0.65271(16) 0.0664(7) Uani 1 1 d . . .
H43 H 0.6048 0.4140 0.6516 0.080 Uiso 1 1 calc R . .
C44 C 0.5803(2) 0.5823(3) 0.58967(14) 0.0631(7) Uani 1 1 d . . .
H44 H 0.6026 0.5446 0.5456 0.076 Uiso 1 1 calc R . .
C45 C 0.5447(2) 0.7169(2) 0.59078(12) 0.0523(6) Uani 1 1 d . . .
H45 H 0.5437 0.7686 0.5474 0.063 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0606(4) 0.0719(4) 0.0617(4) -0.0131(3) 0.0131(3) 0.0065(3)
Cl2 0.0872(5) 0.0535(4) 0.0707(5) -0.0105(3) -0.0093(4) -0.0059(3)
Cl3 0.0668(5) 0.0933(5) 0.0750(5) -0.0195(4) 0.0093(4) 0.0072(4)
O1 0.0568(10) 0.0368(8) 0.0516(9) -0.0043(7) 0.0127(8) -0.0097(7)
O2 0.0717(12) 0.0496(10) 0.0769(12) 0.0014(9) 0.0276(9) -0.0205(9)
O3 0.0672(11) 0.0565(10) 0.0530(10) -0.0013(8) 0.0167(8) -0.0148(8)
O4 0.1071(15) 0.0663(12) 0.0850(14) 0.0005(10) 0.0371(11) -0.0307(11)
O5 0.0673(11) 0.0476(9) 0.0555(10) 0.0032(8) 0.0015(9) -0.0066(8)
O6 0.0917(13) 0.0582(11) 0.0647(11) 0.0117(9) 0.0074(10) -0.0245(10)
C1 0.0414(13) 0.0376(12) 0.0385(12) -0.0010(9) 0.0025(10) -0.0066(10)
C2 0.0463(14) 0.0372(12) 0.0518(14) -0.0037(10) 0.0017(11) -0.0007(10)
C3 0.0379(13) 0.0526(14) 0.0444(13) -0.0083(11) 0.0010(10) 0.0004(10)
C4 0.0478(15) 0.0592(16) 0.0461(14) 0.0025(12) 0.0049(11) -0.0134(12)
C5 0.0442(14) 0.0432(13) 0.0506(14) -0.0013(11) 0.0002(11) -0.0089(10)
C6 0.0400(12) 0.0351(12) 0.0401(12) -0.0017(9) -0.0016(10) -0.0086(9)
C7 0.0385(13) 0.0350(12) 0.0434(13) -0.0047(10) -0.0054(10) -0.0067(9)
C8 0.0450(13) 0.0361(12) 0.0489(13) -0.0083(10) 0.0049(10) -0.0039(10)
C9 0.0493(15) 0.0407(13) 0.0487(14) -0.0037(11) 0.0047(11) -0.0064(11)
C10 0.0416(13) 0.0367(12) 0.0449(13) -0.0049(9) -0.0006(10) -0.0083(10)
C11 0.0487(14) 0.0402(13) 0.0611(15) -0.0062(11) -0.0019(11) -0.0102(11)
C12 0.0671(18) 0.0429(14) 0.0737(17) -0.0082(12) -0.0006(13) -0.0232(13)
C13 0.081(2) 0.0340(13) 0.0668(17) -0.0081(11) 0.0033(14) -0.0090(13)
C14 0.0557(16) 0.0397(14) 0.0750(17) -0.0033(12) 0.0049(13) 0.0026(11)
C15 0.0448(14) 0.0401(13) 0.0659(16) -0.0070(11) 0.0040(11) -0.0084(11)
C16 0.0496(14) 0.0516(14) 0.0411(13) 0.0020(11) -0.0033(11) -0.0101(11)
C17 0.0479(14) 0.0602(15) 0.0440(13) -0.0059(12) 0.0023(11) -0.0056(12)
C18 0.0576(15) 0.0491(14) 0.0469(14) -0.0034(11) -0.0110(12) -0.0063(11)
C19 0.0714(18) 0.0589(16) 0.0528(16) 0.0024(12) 0.0007(13) -0.0192(13)
C20 0.0628(17) 0.0593(16) 0.0506(15) -0.0024(12) 0.0093(12) -0.0134(13)
C21 0.0426(13) 0.0562(14) 0.0367(13) -0.0003(11) -0.0006(10) -0.0065(11)
C22 0.0475(14) 0.0554(15) 0.0420(13) -0.0025(11) -0.0037(11) -0.0050(11)
C23 0.0652(17) 0.0513(15) 0.0530(15) -0.0046(12) 0.0053(13) -0.0056(12)
C24 0.0702(18) 0.0537(16) 0.0584(16) 0.0004(13) 0.0110(13) -0.0121(13)
C25 0.0544(16) 0.0505(14) 0.0462(14) 0.0013(11) 0.0046(12) -0.0027(11)
C26 0.0586(17) 0.0685(17) 0.0619(17) -0.0102(13) 0.0058(13) -0.0058(13)
C27 0.0624(18) 0.0716(19) 0.080(2) 0.0039(16) 0.0221(16) -0.0021(14)
C28 0.104(3) 0.0542(17) 0.0644(19) 0.0006(14) 0.0289(17) 0.0072(16)
C29 0.106(2) 0.0619(18) 0.0571(18) -0.0145(13) 0.0096(17) -0.0067(16)
C30 0.0723(18) 0.0578(16) 0.0543(16) -0.0065(12) 0.0023(14) -0.0089(13)
C31 0.0481(15) 0.0505(14) 0.0457(14) 0.0044(11) -0.0056(11) -0.0078(11)
C32 0.0631(17) 0.0505(14) 0.0528(15) -0.0030(12) -0.0101(13) 0.0008(12)
C33 0.0487(15) 0.0653(17) 0.0465(14) -0.0076(12) -0.0058(11) 0.0033(12)
C34 0.0482(15) 0.0692(18) 0.0528(16) -0.0008(13) -0.0010(12) -0.0111(13)
C35 0.0489(15) 0.0503(14) 0.0500(14) -0.0017(11) -0.0051(11) -0.0104(11)
C36 0.0445(14) 0.0452(13) 0.0402(13) 0.0000(10) -0.0087(11) -0.0040(10)
C37 0.0425(13) 0.0495(14) 0.0385(13) 0.0006(10) -0.0085(10) -0.0081(11)
C38 0.0534(15) 0.0546(15) 0.0449(14) 0.0009(11) -0.0004(11) -0.0064(12)
C39 0.0597(16) 0.0541(16) 0.0507(15) 0.0041(12) -0.0094(12) -0.0087(13)
C40 0.0402(13) 0.0469(13) 0.0449(13) -0.0021(11) -0.0031(10) -0.0086(10)
C41 0.0573(16) 0.0494(14) 0.0498(15) -0.0035(11) -0.0029(12) -0.0063(11)
C42 0.0623(17) 0.0499(15) 0.0713(18) 0.0061(13) -0.0041(13) -0.0086(12)
C43 0.0578(17) 0.0506(15) 0.091(2) -0.0127(15) -0.0003(15) -0.0059(12)
C44 0.0532(16) 0.0687(18) 0.0703(18) -0.0260(15) 0.0069(13) -0.0116(13)
C45 0.0440(14) 0.0647(16) 0.0489(15) -0.0057(12) 0.0030(11) -0.0113(12)
_geom_special_details            
;
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.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C3 1.736(2) . ?
Cl2 C18 1.735(2) . ?
Cl3 C33 1.733(2) . ?
O1 C9 1.375(2) . ?
O1 C1 1.377(2) . ?
O2 C9 1.201(2) . ?
O3 C16 1.376(2) . ?
O3 C24 1.385(3) . ?
O4 C24 1.199(2) . ?
O5 C31 1.381(2) . ?
O5 C39 1.381(3) . ?
O6 C39 1.208(2) . ?
C1 C2 1.377(3) . ?
C1 C6 1.390(2) . ?
C2 C3 1.369(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(3) . ?
C4 C5 1.372(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.454(3) . ?
C7 C8 1.348(2) . ?
C7 C10 1.479(3) . ?
C8 C9 1.446(3) . ?
C8 H8 0.9300 . ?
C10 C15 1.391(3) . ?
C10 C11 1.393(3) . ?
C11 C12 1.382(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.387(3) . ?
C16 C21 1.387(3) . ?
C17 C18 1.370(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.390(3) . ?
C19 C20 1.369(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.404(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.447(3) . ?
C22 C23 1.352(3) . ?
C22 C25 1.482(3) . ?
C23 C24 1.435(3) . ?
C23 H23 0.9300 . ?
C25 C30 1.386(3) . ?
C25 C26 1.387(3) . ?
C26 C27 1.386(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.377(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.368(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.382(3) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C32 1.373(3) . ?
C31 C36 1.395(3) . ?
C32 C33 1.370(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.383(3) . ?
C34 C35 1.370(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.408(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.457(3) . ?
C37 C38 1.347(3) . ?
C37 C40 1.475(3) . ?
C38 C39 1.438(3) . ?
C38 H38 0.9300 . ?
C40 C41 1.392(3) . ?
C40 C45 1.395(3) . ?
C41 C42 1.383(3) . ?
C41 H41 0.9300 . ?
C42 C43 1.370(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.366(3) . ?
C43 H43 0.9300 . ?
C44 C45 1.384(3) . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C1 121.72(16) . . ?
C16 O3 C24 121.43(18) . . ?
C31 O5 C39 121.41(18) . . ?
O1 C1 C2 115.32(17) . . ?
O1 C1 C6 121.43(17) . . ?
C2 C1 C6 123.24(18) . . ?
C3 C2 C1 118.31(19) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 120.96(19) . . ?
C2 C3 Cl1 119.34(16) . . ?
C4 C3 Cl1 119.70(16) . . ?
C5 C4 C3 119.54(19) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.57(19) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 116.32(18) . . ?
C1 C6 C7 118.36(16) . . ?
C5 C6 C7 125.21(18) . . ?
C8 C7 C6 118.45(18) . . ?
C8 C7 C10 119.82(18) . . ?
C6 C7 C10 121.69(16) . . ?
C7 C8 C9 122.84(19) . . ?
C7 C8 H8 118.6 . . ?
C9 C8 H8 118.6 . . ?
O2 C9 O1 116.23(19) . . ?
O2 C9 C8 126.9(2) . . ?
O1 C9 C8 116.85(17) . . ?
C15 C10 C11 118.77(19) . . ?
C15 C10 C7 118.98(18) . . ?
C11 C10 C7 122.21(18) . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.8(2) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
O3 C16 C17 115.29(19) . . ?
O3 C16 C21 121.6(2) . . ?
C17 C16 C21 123.1(2) . . ?
C18 C17 C16 118.4(2) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C17 C18 C19 120.9(2) . . ?
C17 C18 Cl2 119.58(18) . . ?
C19 C18 Cl2 119.47(18) . . ?
C20 C19 C18 119.4(2) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 122.0(2) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?
C16 C21 C20 116.2(2) . . ?
C16 C21 C22 118.53(19) . . ?
C20 C21 C22 125.2(2) . . ?
C23 C22 C21 118.2(2) . . ?
C23 C22 C25 119.5(2) . . ?
C21 C22 C25 122.21(19) . . ?
C22 C23 C24 123.4(2) . . ?
C22 C23 H23 118.3 . . ?
C24 C23 H23 118.3 . . ?
O4 C24 O3 117.2(2) . . ?
O4 C24 C23 126.2(2) . . ?
O3 C24 C23 116.6(2) . . ?
C30 C25 C26 119.1(2) . . ?
C30 C25 C22 119.1(2) . . ?
C26 C25 C22 121.8(2) . . ?
C27 C26 C25 120.4(3) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C28 C27 C26 119.7(3) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C29 C28 C27 120.4(3) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 120.3(3) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C25 120.2(2) . . ?
C29 C30 H30 119.9 . . ?
C25 C30 H30 119.9 . . ?
C32 C31 O5 115.2(2) . . ?
C32 C31 C36 123.6(2) . . ?
O5 C31 C36 121.2(2) . . ?
C33 C32 C31 118.0(2) . . ?
C33 C32 H32 121.0 . . ?
C31 C32 H32 121.0 . . ?
C32 C33 C34 121.3(2) . . ?
C32 C33 Cl3 119.3(2) . . ?
C34 C33 Cl3 119.45(18) . . ?
C35 C34 C33 119.6(2) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C36 121.5(2) . . ?
C34 C35 H35 119.2 . . ?
C36 C35 H35 119.2 . . ?
C31 C36 C35 115.77(19) . . ?
C31 C36 C37 118.74(18) . . ?
C35 C36 C37 125.5(2) . . ?
C38 C37 C36 117.7(2) . . ?
C38 C37 C40 120.2(2) . . ?
C36 C37 C40 122.02(18) . . ?
C37 C38 C39 123.6(2) . . ?
C37 C38 H38 118.2 . . ?
C39 C38 H38 118.2 . . ?
O6 C39 O5 116.5(2) . . ?
O6 C39 C38 126.5(2) . . ?
O5 C39 C38 117.0(2) . . ?
C41 C40 C45 117.6(2) . . ?
C41 C40 C37 122.2(2) . . ?
C45 C40 C37 120.14(19) . . ?
C42 C41 C40 120.7(2) . . ?
C42 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
C43 C42 C41 120.7(2) . . ?
C43 C42 H42 119.6 . . ?
C41 C42 H42 119.6 . . ?
C44 C43 C42 119.5(2) . . ?
C44 C43 H43 120.2 . . ?
C42 C43 H43 120.2 . . ?
C43 C44 C45 120.6(2) . . ?
C43 C44 H44 119.7 . . ?
C45 C44 H44 119.7 . . ?
C44 C45 C40 120.8(2) . . ?
C44 C45 H45 119.6 . . ?
C40 C45 H45 119.6 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C1 C2 -174.12(18) . . . . ?
C9 O1 C1 C6 4.6(3) . . . . ?
O1 C1 C2 C3 176.78(17) . . . . ?
C6 C1 C2 C3 -1.9(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C3 Cl1 179.79(16) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
Cl1 C3 C4 C5 -178.60(16) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
O1 C1 C6 C5 -175.73(17) . . . . ?
C2 C1 C6 C5 2.9(3) . . . . ?
O1 C1 C6 C7 0.6(3) . . . . ?
C2 C1 C6 C7 179.27(19) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C4 C5 C6 C7 -177.7(2) . . . . ?
C1 C6 C7 C8 -3.3(3) . . . . ?
C5 C6 C7 C8 172.73(19) . . . . ?
C1 C6 C7 C10 178.77(18) . . . . ?
C5 C6 C7 C10 -5.2(3) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C10 C7 C8 C9 178.92(19) . . . . ?
C1 O1 C9 O2 173.68(19) . . . . ?
C1 O1 C9 C8 -6.8(3) . . . . ?
C7 C8 C9 O2 -176.5(2) . . . . ?
C7 C8 C9 O1 4.0(3) . . . . ?
C8 C7 C10 C15 -47.6(3) . . . . ?
C6 C7 C10 C15 130.3(2) . . . . ?
C8 C7 C10 C11 130.2(2) . . . . ?
C6 C7 C10 C11 -51.8(3) . . . . ?
C15 C10 C11 C12 -0.2(3) . . . . ?
C7 C10 C11 C12 -178.08(19) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C10 0.1(3) . . . . ?
C11 C10 C15 C14 0.2(3) . . . . ?
C7 C10 C15 C14 178.2(2) . . . . ?
C24 O3 C16 C17 174.47(19) . . . . ?
C24 O3 C16 C21 -4.7(3) . . . . ?
O3 C16 C17 C18 -178.81(19) . . . . ?
C21 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C16 C17 C18 Cl2 178.62(16) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
Cl2 C18 C19 C20 -178.60(18) . . . . ?
C18 C19 C20 C21 -0.4(4) . . . . ?
O3 C16 C21 C20 178.1(2) . . . . ?
C17 C16 C21 C20 -1.0(3) . . . . ?
O3 C16 C21 C22 0.6(3) . . . . ?
C17 C16 C21 C22 -178.5(2) . . . . ?
C19 C20 C21 C16 1.0(3) . . . . ?
C19 C20 C21 C22 178.3(2) . . . . ?
C16 C21 C22 C23 2.4(3) . . . . ?
C20 C21 C22 C23 -174.8(2) . . . . ?
C16 C21 C22 C25 -179.2(2) . . . . ?
C20 C21 C22 C25 3.5(3) . . . . ?
C21 C22 C23 C24 -1.5(3) . . . . ?
C25 C22 C23 C24 -179.9(2) . . . . ?
C16 O3 C24 O4 -176.3(2) . . . . ?
C16 O3 C24 C23 5.4(3) . . . . ?
C22 C23 C24 O4 179.5(2) . . . . ?
C22 C23 C24 O3 -2.4(3) . . . . ?
C23 C22 C25 C30 52.8(3) . . . . ?
C21 C22 C25 C30 -125.5(2) . . . . ?
C23 C22 C25 C26 -125.2(3) . . . . ?
C21 C22 C25 C26 56.4(3) . . . . ?
C30 C25 C26 C27 -0.4(4) . . . . ?
C22 C25 C26 C27 177.7(2) . . . . ?
C25 C26 C27 C28 0.7(4) . . . . ?
C26 C27 C28 C29 -0.1(4) . . . . ?
C27 C28 C29 C30 -0.7(4) . . . . ?
C28 C29 C30 C25 1.0(4) . . . . ?
C26 C25 C30 C29 -0.4(4) . . . . ?
C22 C25 C30 C29 -178.6(2) . . . . ?
C39 O5 C31 C32 -177.94(19) . . . . ?
C39 O5 C31 C36 2.2(3) . . . . ?
O5 C31 C32 C33 177.36(18) . . . . ?
C36 C31 C32 C33 -2.8(3) . . . . ?
C31 C32 C33 C34 -1.6(3) . . . . ?
C31 C32 C33 Cl3 178.72(17) . . . . ?
C32 C33 C34 C35 3.1(3) . . . . ?
Cl3 C33 C34 C35 -177.21(17) . . . . ?
C33 C34 C35 C36 -0.4(3) . . . . ?
C32 C31 C36 C35 5.2(3) . . . . ?
O5 C31 C36 C35 -174.90(18) . . . . ?
C32 C31 C36 C37 -176.6(2) . . . . ?
O5 C31 C36 C37 3.2(3) . . . . ?
C34 C35 C36 C31 -3.6(3) . . . . ?
C34 C35 C36 C37 178.4(2) . . . . ?
C31 C36 C37 C38 -5.6(3) . . . . ?
C35 C36 C37 C38 172.3(2) . . . . ?
C31 C36 C37 C40 173.62(19) . . . . ?
C35 C36 C37 C40 -8.4(3) . . . . ?
C36 C37 C38 C39 2.8(3) . . . . ?
C40 C37 C38 C39 -176.4(2) . . . . ?
C31 O5 C39 O6 176.80(19) . . . . ?
C31 O5 C39 C38 -5.0(3) . . . . ?
C37 C38 C39 O6 -179.6(2) . . . . ?
C37 C38 C39 O5 2.4(3) . . . . ?
C38 C37 C40 C41 136.5(2) . . . . ?
C36 C37 C40 C41 -42.7(3) . . . . ?
C38 C37 C40 C45 -41.5(3) . . . . ?
C36 C37 C40 C45 139.3(2) . . . . ?
C45 C40 C41 C42 -1.7(3) . . . . ?
C37 C40 C41 C42 -179.8(2) . . . . ?
C40 C41 C42 C43 0.2(4) . . . . ?
C41 C42 C43 C44 1.4(4) . . . . ?
C42 C43 C44 C45 -1.4(4) . . . . ?
C43 C44 C45 C40 -0.2(3) . . . . ?
C41 C40 C45 C44 1.7(3) . . . . ?
C37 C40 C45 C44 179.83(19) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C38 H38 O2 0.93 2.39 3.311(3) 169.1 1_665
C13 H13 O1 0.93 2.46 3.343(3) 159.2 1_565
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.86
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.049
# Attachment 'shelxl.res'