# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_110915masudaCl2 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C18 H16 Cl2 O2' _chemical_formula_moiety 'C18 H16 Cl2 O2' _chemical_formula_weight 335.23 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 15.7021(2) _cell_length_b 9.69233(10) _cell_length_c 10.9905(2) _cell_angle_alpha 90.0000 _cell_angle_beta 93.5974(10) _cell_angle_gamma 90.0000 _cell_volume 1669.34(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 11116 _cell_measurement_theta_min 4.03 _cell_measurement_theta_max 68.27 _cell_measurement_temperature 173 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.070 _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696.00 _exptl_absorpt_coefficient_mu 3.527 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.443 _exptl_absorpt_correction_T_max 0.781 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 173 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.000 _diffrn_reflns_number 14232 _diffrn_reflns_av_R_equivalents 0.0958 _diffrn_reflns_theta_max 68.25 _diffrn_reflns_theta_full 68.25 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3028 _reflns_number_gt 2127 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1675 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3028 _refine_ls_number_parameters 200 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0687P)^2^+0.3960P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.370 _refine_diff_density_min -0.370 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0082(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.3639 0.7018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.98591(6) 0.20501(8) 0.66500(8) 0.0621(4) Uani 1.0 4 d . . . Cl2 Cl 0.27562(6) 0.77981(10) 0.14935(10) 0.0730(4) Uani 1.0 4 d . . . O1 O 0.78367(14) 0.6915(3) 0.3302(2) 0.0548(6) Uani 1.0 4 d . . . O2 O 0.62271(13) 0.6229(2) 0.5006(2) 0.0527(6) Uani 1.0 4 d . . . C1 C 0.75648(19) 0.8004(3) 0.5183(3) 0.0411(7) Uani 1.0 4 d . . . C2 C 0.8237(2) 0.9151(4) 0.5320(4) 0.0596(9) Uani 1.0 4 d . . . C3 C 0.79252(18) 0.6860(3) 0.4412(3) 0.0422(7) Uani 1.0 4 d . . . C4 C 0.84219(17) 0.5705(3) 0.5022(3) 0.0374(7) Uani 1.0 4 d . . . C5 C 0.88242(17) 0.4778(3) 0.4290(3) 0.0428(7) Uani 1.0 4 d . . . C6 C 0.92685(18) 0.3655(3) 0.4780(3) 0.0446(8) Uani 1.0 4 d . . . C7 C 0.93012(18) 0.3459(3) 0.6030(3) 0.0437(8) Uani 1.0 4 d . . . C8 C 0.89137(19) 0.4373(4) 0.6783(3) 0.0506(8) Uani 1.0 4 d . . . C9 C 0.84720(19) 0.5492(3) 0.6277(3) 0.0458(8) Uani 1.0 4 d . . . C11 C 0.67124(18) 0.8504(3) 0.4587(3) 0.0423(7) Uani 1.0 4 d . . . C12 C 0.6311(2) 0.9638(4) 0.5345(4) 0.0618(10) Uani 1.0 4 d . . . C13 C 0.60833(19) 0.7310(3) 0.4456(3) 0.0429(8) Uani 1.0 4 d . . . C14 C 0.52685(18) 0.7471(3) 0.3694(3) 0.0399(7) Uani 1.0 4 d . . . C15 C 0.45948(18) 0.6592(3) 0.3903(3) 0.0456(8) Uani 1.0 4 d . . . C16 C 0.38197(19) 0.6682(3) 0.3244(3) 0.0486(8) Uani 1.0 4 d . . . C17 C 0.3718(2) 0.7658(4) 0.2347(3) 0.0470(8) Uani 1.0 4 d . . . C18 C 0.4371(2) 0.8563(4) 0.2112(3) 0.0527(9) Uani 1.0 4 d . . . C19 C 0.5145(2) 0.8469(3) 0.2791(3) 0.0485(8) Uani 1.0 4 d . . . H1 H 0.7466 0.7625 0.6009 0.0493 Uiso 1.0 4 calc R . . H2A H 0.8339 0.9530 0.4515 0.0715 Uiso 1.0 4 calc R . . H2B H 0.8771 0.8772 0.5692 0.0715 Uiso 1.0 4 calc R . . H2C H 0.8032 0.9885 0.5840 0.0715 Uiso 1.0 4 calc R . . H5 H 0.8794 0.4915 0.3433 0.0514 Uiso 1.0 4 calc R . . H6 H 0.9546 0.3031 0.4269 0.0535 Uiso 1.0 4 calc R . . H8 H 0.8949 0.4235 0.7641 0.0608 Uiso 1.0 4 calc R . . H9 H 0.8201 0.6121 0.6791 0.0550 Uiso 1.0 4 calc R . . H11 H 0.6810 0.8879 0.3760 0.0507 Uiso 1.0 4 calc R . . H12A H 0.5802 1.0004 0.4894 0.0741 Uiso 1.0 4 calc R . . H12B H 0.6724 1.0383 0.5504 0.0741 Uiso 1.0 4 calc R . . H12C H 0.6150 0.9248 0.6121 0.0741 Uiso 1.0 4 calc R . . H15 H 0.4670 0.5907 0.4520 0.0547 Uiso 1.0 4 calc R . . H16 H 0.3365 0.6078 0.3409 0.0584 Uiso 1.0 4 calc R . . H18 H 0.4290 0.9242 0.1492 0.0632 Uiso 1.0 4 calc R . . H19 H 0.5594 0.9090 0.2637 0.0582 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0655(6) 0.0563(6) 0.0651(7) 0.0157(4) 0.0096(5) 0.0153(4) Cl2 0.0540(6) 0.0768(7) 0.0859(9) 0.0088(5) -0.0147(5) 0.0091(5) O1 0.0663(15) 0.0613(14) 0.0365(13) 0.0160(11) 0.0014(11) 0.0029(11) O2 0.0524(13) 0.0384(12) 0.0662(16) -0.0000(10) -0.0046(11) 0.0131(11) C1 0.0433(17) 0.0387(16) 0.0411(18) -0.0001(12) 0.0022(14) -0.0019(13) C2 0.055(2) 0.0495(19) 0.074(3) -0.0074(15) 0.0015(18) -0.0080(18) C3 0.0383(16) 0.0422(17) 0.0463(19) -0.0027(13) 0.0045(14) 0.0006(14) C4 0.0354(14) 0.0393(15) 0.0375(17) -0.0041(12) 0.0017(12) 0.0012(13) C5 0.0381(15) 0.0453(17) 0.0447(19) -0.0030(13) 0.0002(13) -0.0014(14) C6 0.0401(16) 0.0429(17) 0.050(2) 0.0001(13) 0.0001(14) -0.0054(14) C7 0.0394(16) 0.0422(16) 0.049(2) -0.0016(13) 0.0014(14) 0.0043(15) C8 0.0538(19) 0.056(2) 0.0424(19) 0.0029(15) 0.0068(15) 0.0037(15) C9 0.0513(18) 0.0464(17) 0.0401(19) 0.0061(14) 0.0047(14) -0.0005(14) C11 0.0442(17) 0.0349(15) 0.0481(19) -0.0022(13) 0.0063(14) 0.0008(14) C12 0.056(2) 0.0413(18) 0.088(3) 0.0042(15) 0.0066(18) -0.0166(18) C13 0.0429(17) 0.0355(16) 0.0508(19) 0.0039(13) 0.0057(15) 0.0033(14) C14 0.0462(17) 0.0285(14) 0.0454(19) 0.0062(12) 0.0054(14) -0.0000(13) C15 0.0467(17) 0.0325(15) 0.058(2) 0.0024(13) 0.0069(15) 0.0076(14) C16 0.0432(18) 0.0400(16) 0.063(3) 0.0014(14) 0.0043(16) 0.0024(16) C17 0.0471(18) 0.0462(17) 0.047(2) 0.0100(14) -0.0015(15) -0.0017(15) C18 0.058(2) 0.0481(18) 0.052(3) 0.0040(15) 0.0006(16) 0.0148(16) C19 0.0503(18) 0.0405(17) 0.055(2) 0.0004(14) 0.0045(15) 0.0032(16) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Cl1 C7 1.738(3) yes . . Cl2 C17 1.732(4) yes . . O1 C3 1.220(4) yes . . O2 C13 1.223(4) yes . . C1 C2 1.535(5) yes . . C1 C3 1.526(5) yes . . C1 C11 1.532(4) yes . . C3 C4 1.499(4) yes . . C4 C5 1.385(4) yes . . C4 C9 1.391(5) yes . . C5 C6 1.383(4) yes . . C6 C7 1.384(5) yes . . C7 C8 1.380(5) yes . . C8 C9 1.386(5) yes . . C11 C12 1.538(5) yes . . C11 C13 1.523(4) yes . . C13 C14 1.493(4) yes . . C14 C15 1.389(4) yes . . C14 C19 1.391(5) yes . . C15 C16 1.380(5) yes . . C16 C17 1.369(5) yes . . C17 C18 1.386(5) yes . . C18 C19 1.389(5) yes . . C1 H1 1.000 no . . C2 H2A 0.980 no . . C2 H2B 0.980 no . . C2 H2C 0.980 no . . C5 H5 0.950 no . . C6 H6 0.950 no . . C8 H8 0.950 no . . C9 H9 0.950 no . . C11 H11 1.000 no . . C12 H12A 0.980 no . . C12 H12B 0.980 no . . C12 H12C 0.980 no . . C15 H15 0.950 no . . C16 H16 0.950 no . . C18 H18 0.950 no . . C19 H19 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C2 C1 C3 107.7(3) yes . . . C2 C1 C11 112.9(3) yes . . . C3 C1 C11 109.7(3) yes . . . O1 C3 C1 120.1(3) yes . . . O1 C3 C4 120.2(3) yes . . . C1 C3 C4 119.7(3) yes . . . C3 C4 C5 117.9(3) yes . . . C3 C4 C9 123.3(3) yes . . . C5 C4 C9 118.7(3) yes . . . C4 C5 C6 121.4(3) yes . . . C5 C6 C7 118.7(3) yes . . . Cl1 C7 C6 118.9(3) yes . . . Cl1 C7 C8 120.0(3) yes . . . C6 C7 C8 121.1(3) yes . . . C7 C8 C9 119.3(3) yes . . . C4 C9 C8 120.7(3) yes . . . C1 C11 C12 111.8(3) yes . . . C1 C11 C13 110.1(3) yes . . . C12 C11 C13 108.0(3) yes . . . O2 C13 C11 120.4(3) yes . . . O2 C13 C14 119.5(3) yes . . . C11 C13 C14 120.1(3) yes . . . C13 C14 C15 118.6(3) yes . . . C13 C14 C19 123.3(3) yes . . . C15 C14 C19 118.1(3) yes . . . C14 C15 C16 122.0(3) yes . . . C15 C16 C17 118.8(3) yes . . . Cl2 C17 C16 120.2(3) yes . . . Cl2 C17 C18 118.7(3) yes . . . C16 C17 C18 121.1(3) yes . . . C17 C18 C19 119.4(3) yes . . . C14 C19 C18 120.5(3) yes . . . C2 C1 H1 108.810 no . . . C3 C1 H1 108.816 no . . . C11 C1 H1 108.816 no . . . C1 C2 H2A 109.467 no . . . C1 C2 H2B 109.472 no . . . C1 C2 H2C 109.468 no . . . H2A C2 H2B 109.470 no . . . H2A C2 H2C 109.473 no . . . H2B C2 H2C 109.478 no . . . C4 C5 H5 119.281 no . . . C6 C5 H5 119.282 no . . . C5 C6 H6 120.625 no . . . C7 C6 H6 120.628 no . . . C7 C8 H8 120.326 no . . . C9 C8 H8 120.333 no . . . C4 C9 H9 119.670 no . . . C8 C9 H9 119.676 no . . . C1 C11 H11 108.955 no . . . C12 C11 H11 108.964 no . . . C13 C11 H11 108.964 no . . . C11 C12 H12A 109.472 no . . . C11 C12 H12B 109.480 no . . . C11 C12 H12C 109.474 no . . . H12A C12 H12B 109.470 no . . . H12A C12 H12C 109.460 no . . . H12B C12 H12C 109.472 no . . . C14 C15 H15 119.006 no . . . C16 C15 H15 119.003 no . . . C15 C16 H16 120.587 no . . . C17 C16 H16 120.579 no . . . C17 C18 H18 120.302 no . . . C19 C18 H18 120.292 no . . . C14 C19 H19 119.742 no . . . C18 C19 H19 119.744 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C2 C1 C3 O1 -86.4(3) no . . . . C2 C1 C3 C4 90.8(3) no . . . . C2 C1 C11 C12 -61.2(4) no . . . . C2 C1 C11 C13 178.8(3) no . . . . C3 C1 C11 C12 178.7(2) no . . . . C3 C1 C11 C13 58.7(3) no . . . . C11 C1 C3 O1 36.8(4) no . . . . C11 C1 C3 C4 -145.9(3) no . . . . O1 C3 C4 C5 4.8(4) no . . . . O1 C3 C4 C9 -172.8(3) no . . . . C1 C3 C4 C5 -172.5(3) no . . . . C1 C3 C4 C9 9.9(4) no . . . . C3 C4 C5 C6 -177.6(3) no . . . . C3 C4 C9 C8 177.4(3) no . . . . C5 C4 C9 C8 -0.2(4) no . . . . C9 C4 C5 C6 0.1(4) no . . . . C4 C5 C6 C7 0.6(4) no . . . . C5 C6 C7 Cl1 -180.0(3) no . . . . C5 C6 C7 C8 -1.2(4) no . . . . Cl1 C7 C8 C9 179.92(19) no . . . . C6 C7 C8 C9 1.1(5) no . . . . C7 C8 C9 C4 -0.4(5) no . . . . C1 C11 C13 O2 14.1(4) no . . . . C1 C11 C13 C14 -168.4(3) no . . . . C12 C11 C13 O2 -108.3(3) no . . . . C12 C11 C13 C14 69.2(4) no . . . . O2 C13 C14 C15 18.9(5) no . . . . O2 C13 C14 C19 -161.8(3) no . . . . C11 C13 C14 C15 -158.6(3) no . . . . C11 C13 C14 C19 20.7(5) no . . . . C13 C14 C15 C16 179.5(3) no . . . . C13 C14 C19 C18 179.9(3) no . . . . C15 C14 C19 C18 -0.8(5) no . . . . C19 C14 C15 C16 0.2(5) no . . . . C14 C15 C16 C17 0.8(5) no . . . . C15 C16 C17 Cl2 179.7(3) no . . . . C15 C16 C17 C18 -1.2(5) no . . . . Cl2 C17 C18 C19 179.8(2) no . . . . C16 C17 C18 C19 0.6(5) no . . . . C17 C18 C19 C14 0.4(5) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O1 O2 3.306(4) no . . O1 C2 3.136(5) no . . O1 C5 2.768(4) no . . O1 C11 2.792(4) no . . O1 C13 3.126(4) no . . O2 C1 2.712(4) no . . O2 C3 2.851(4) no . . O2 C4 3.483(4) no . . O2 C12 3.326(4) no . . O2 C15 2.788(4) no . . C1 C9 3.031(4) no . . C2 C4 3.371(5) no . . C2 C12 3.064(5) no . . C3 C13 2.928(5) no . . C4 C7 2.771(4) no . . C5 C8 2.763(5) no . . C6 C9 2.774(5) no . . C11 C19 3.058(5) no . . C12 C14 3.164(5) no . . C12 C19 3.446(5) no . . C14 C17 2.776(5) no . . C15 C18 2.751(5) no . . C16 C19 2.776(5) no . . Cl2 C5 3.211(3) no . 2_655 Cl2 C6 3.493(3) no . 2_655 O1 C1 3.429(4) no . 4_564 O1 C2 3.531(5) no . 4_564 O1 C9 3.542(4) no . 4_564 O2 C15 3.282(4) no . 3_666 O2 C16 3.418(4) no . 3_666 O2 C18 3.564(4) no . 2_645 C1 O1 3.429(4) no . 4_565 C2 O1 3.531(5) no . 4_565 C5 Cl2 3.211(3) no . 2_645 C5 C6 3.455(4) no . 3_766 C5 C7 3.441(4) no . 3_766 C6 Cl2 3.493(3) no . 2_645 C6 C5 3.455(4) no . 3_766 C6 C6 3.488(5) no . 3_766 C7 C5 3.441(4) no . 3_766 C9 O1 3.542(4) no . 4_565 C12 C18 3.518(5) no . 3_676 C15 O2 3.282(4) no . 3_666 C15 C18 3.567(5) no . 2_645 C15 C18 3.568(5) no . 4_565 C15 C19 3.590(5) no . 2_645 C16 O2 3.418(4) no . 3_666 C18 O2 3.564(4) no . 2_655 C18 C12 3.518(5) no . 3_676 C18 C15 3.567(5) no . 2_655 C18 C15 3.568(5) no . 4_564 C19 C15 3.590(5) no . 2_655 Cl1 H6 2.7985 no . . Cl1 H8 2.8121 no . . Cl2 H16 2.8061 no . . Cl2 H18 2.7858 no . . O1 H1 3.1434 no . . O1 H2A 2.9479 no . . O1 H2B 3.4354 no . . O1 H5 2.4517 no . . O1 H11 2.5646 no . . O2 H1 2.5610 no . . O2 H9 3.5635 no . . O2 H11 3.0768 no . . O2 H12C 3.1776 no . . O2 H15 2.4897 no . . C1 H9 2.6885 no . . C1 H12A 3.3779 no . . C1 H12B 2.6913 no . . C1 H12C 2.7825 no . . C2 H9 3.3551 no . . C2 H11 2.7486 no . . C2 H12B 2.6781 no . . C2 H12C 3.4488 no . . C3 H2A 2.6683 no . . C3 H2B 2.6341 no . . C3 H2C 3.3249 no . . C3 H5 2.5997 no . . C3 H9 2.7196 no . . C3 H11 2.6928 no . . C4 H1 2.6649 no . . C4 H2B 3.1027 no . . C4 H6 3.2709 no . . C4 H8 3.2706 no . . C5 H9 3.2472 no . . C6 H8 3.2631 no . . C7 H5 3.2382 no . . C7 H9 3.2440 no . . C8 H6 3.2642 no . . C9 H1 2.6080 no . . C9 H2B 3.2825 no . . C9 H5 3.2458 no . . C11 H2A 2.7470 no . . C11 H2B 3.3903 no . . C11 H2C 2.7609 no . . C11 H19 2.7444 no . . C12 H1 2.7309 no . . C12 H2A 3.3697 no . . C12 H2C 2.7338 no . . C12 H19 3.1606 no . . C13 H1 2.6930 no . . C13 H12A 2.6962 no . . C13 H12B 3.3267 no . . C13 H12C 2.6200 no . . C13 H15 2.6075 no . . C13 H19 2.7156 no . . C14 H11 2.7753 no . . C14 H12A 2.8857 no . . C14 H12C 3.3960 no . . C14 H16 3.2768 no . . C14 H18 3.2714 no . . C15 H19 3.2460 no . . C16 H18 3.2540 no . . C17 H15 3.2206 no . . C17 H19 3.2537 no . . C18 H16 3.2582 no . . C19 H11 2.7886 no . . C19 H12A 2.8846 no . . C19 H15 3.2419 no . . H1 H2A 2.8754 no . . H1 H2B 2.3760 no . . H1 H2C 2.3756 no . . H1 H9 2.0183 no . . H1 H11 2.8860 no . . H1 H12B 2.9540 no . . H1 H12C 2.6058 no . . H2A H11 2.5704 no . . H2A H12B 2.9398 no . . H2B H9 2.9997 no . . H2B H12B 3.5671 no . . H2C H11 3.0518 no . . H2C H12A 3.5916 no . . H2C H12B 2.1189 no . . H2C H12C 3.0539 no . . H5 H6 2.3315 no . . H8 H9 2.3357 no . . H11 H12A 2.3439 no . . H11 H12B 2.4191 no . . H11 H12C 2.8768 no . . H11 H19 2.2172 no . . H12A H19 2.6347 no . . H15 H16 2.3240 no . . H18 H19 2.3391 no . . Cl1 H2A 3.5271 no . 3_766 Cl1 H2B 3.5472 no . 3_766 Cl1 H5 3.2673 no . 4_555 Cl1 H6 2.9515 no . 4_555 Cl1 H8 3.3715 no . 2_746 Cl1 H9 3.5177 no . 2_746 Cl2 H5 3.1887 no . 2_655 Cl2 H8 3.5046 no . 3_666 Cl2 H12B 3.3448 no . 2_645 O1 H1 2.5897 no . 4_564 O1 H2B 3.3695 no . 4_564 O1 H2C 3.2504 no . 4_564 O1 H9 2.6134 no . 4_564 O2 H15 2.5757 no . 3_666 O2 H16 2.8815 no . 3_666 O2 H18 2.6287 no . 2_645 O2 H18 3.5705 no . 4_565 O2 H19 3.1312 no . 4_565 C2 H5 3.5935 no . 4_565 C2 H8 3.5746 no . 4_564 C3 H9 3.5312 no . 4_564 C4 H6 3.4608 no . 3_766 C7 H5 3.3991 no . 3_766 C8 H2A 3.3615 no . 4_565 C8 H16 3.5974 no . 3_666 C9 H2A 3.5783 no . 4_565 C9 H6 3.5111 no . 3_766 C9 H16 3.2983 no . 3_666 C12 H12A 3.3293 no . 3_676 C13 H15 3.5433 no . 3_666 C13 H18 3.1924 no . 2_645 C14 H12A 3.3991 no . 3_676 C14 H18 3.2141 no . 2_645 C15 H15 3.1545 no . 3_666 C15 H18 2.9214 no . 2_645 C15 H18 3.0240 no . 4_565 C15 H19 2.9611 no . 2_645 C16 H11 3.5965 no . 2_645 C16 H12B 3.2957 no . 3_676 C16 H19 2.8651 no . 2_645 C17 H12B 3.1420 no . 3_676 C17 H12C 3.4390 no . 3_676 C18 H12A 3.5984 no . 3_676 C18 H12B 3.3814 no . 3_676 C18 H12C 3.0232 no . 3_676 C18 H15 3.3138 no . 2_655 C18 H15 2.9608 no . 4_564 C19 H12A 3.3699 no . 3_676 C19 H12C 3.2809 no . 3_676 C19 H15 3.4941 no . 2_655 H1 O1 2.5897 no . 4_565 H1 H11 3.5657 no . 4_565 H2A Cl1 3.5271 no . 3_766 H2A C8 3.3615 no . 4_564 H2A C9 3.5783 no . 4_564 H2A H8 2.6155 no . 4_564 H2A H9 3.0539 no . 4_564 H2B Cl1 3.5472 no . 3_766 H2B O1 3.3695 no . 4_565 H2B H5 3.2687 no . 4_565 H2B H6 3.1665 no . 3_766 H2C O1 3.2504 no . 4_565 H2C H5 3.0270 no . 4_565 H5 Cl1 3.2673 no . 4_554 H5 Cl2 3.1887 no . 2_645 H5 C2 3.5935 no . 4_564 H5 C7 3.3991 no . 3_766 H5 H2B 3.2687 no . 4_564 H5 H2C 3.0270 no . 4_564 H6 Cl1 2.9515 no . 4_554 H6 C4 3.4608 no . 3_766 H6 C9 3.5111 no . 3_766 H6 H2B 3.1665 no . 3_766 H6 H8 2.9490 no . 4_554 H8 Cl1 3.3715 no . 2_756 H8 Cl2 3.5046 no . 3_666 H8 C2 3.5746 no . 4_565 H8 H2A 2.6155 no . 4_565 H8 H6 2.9490 no . 4_555 H9 Cl1 3.5177 no . 2_756 H9 O1 2.6134 no . 4_565 H9 C3 3.5312 no . 4_565 H9 H2A 3.0539 no . 4_565 H9 H11 3.1691 no . 4_565 H9 H16 3.2502 no . 3_666 H11 C16 3.5965 no . 2_655 H11 H1 3.5657 no . 4_564 H11 H9 3.1691 no . 4_564 H11 H16 3.1966 no . 2_655 H12A C12 3.3293 no . 3_676 H12A C14 3.3991 no . 3_676 H12A C18 3.5984 no . 3_676 H12A C19 3.3699 no . 3_676 H12A H12A 2.5437 no . 3_676 H12A H12C 3.2756 no . 3_676 H12B Cl2 3.3448 no . 2_655 H12B C16 3.2957 no . 3_676 H12B C17 3.1420 no . 3_676 H12B C18 3.3814 no . 3_676 H12C C17 3.4390 no . 3_676 H12C C18 3.0232 no . 3_676 H12C C19 3.2809 no . 3_676 H12C H12A 3.2756 no . 3_676 H12C H18 3.1190 no . 3_676 H12C H19 3.5239 no . 3_676 H15 O2 2.5757 no . 3_666 H15 C13 3.5433 no . 3_666 H15 C15 3.1545 no . 3_666 H15 C18 3.3138 no . 2_645 H15 C18 2.9608 no . 4_565 H15 C19 3.4941 no . 2_645 H15 H15 2.2682 no . 3_666 H15 H18 2.5950 no . 2_645 H15 H18 2.2884 no . 4_565 H15 H19 2.9606 no . 2_645 H16 O2 2.8815 no . 3_666 H16 C8 3.5974 no . 3_666 H16 C9 3.2983 no . 3_666 H16 H9 3.2502 no . 3_666 H16 H11 3.1966 no . 2_645 H16 H19 2.8185 no . 2_645 H18 O2 2.6287 no . 2_655 H18 O2 3.5705 no . 4_564 H18 C13 3.1924 no . 2_655 H18 C14 3.2141 no . 2_655 H18 C15 2.9214 no . 2_655 H18 C15 3.0240 no . 4_564 H18 H12C 3.1190 no . 3_676 H18 H15 2.5950 no . 2_655 H18 H15 2.2884 no . 4_564 H19 O2 3.1312 no . 4_564 H19 C15 2.9611 no . 2_655 H19 C16 2.8651 no . 2_655 H19 H12C 3.5239 no . 3_676 H19 H15 2.9606 no . 2_655 H19 H16 2.8185 no . 2_655 _database_code_depnum_ccdc_archive 'CCDC 969200' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_110624masuda #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C18 H16 F2 O2' _chemical_formula_moiety 'C18 H16 F2 O2' _chemical_formula_weight 302.32 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 11.1477(5) _cell_length_b 13.3381(6) _cell_length_c 10.5647(5) _cell_angle_alpha 90.0000 _cell_angle_beta 98.775(2) _cell_angle_gamma 90.0000 _cell_volume 1552.47(12) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4464 _cell_measurement_theta_min 3.31 _cell_measurement_theta_max 65.97 _cell_measurement_temperature 277 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.060 _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632.00 _exptl_absorpt_coefficient_mu 0.834 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.619 _exptl_absorpt_correction_T_max 0.951 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 277 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.000 _diffrn_reflns_number 15788 _diffrn_reflns_av_R_equivalents 0.0682 _diffrn_reflns_theta_max 68.19 _diffrn_reflns_theta_full 68.19 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2811 _reflns_number_gt 1282 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.1517 _refine_ls_wR_factor_ref 0.4909 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2811 _refine_ls_number_parameters 200 _refine_ls_goodness_of_fit_ref 1.680 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.740 _refine_diff_density_min -0.360 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.28(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; F F 0.0727 0.0534 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 F1 F 0.7801(4) 0.1247(4) 0.9258(5) 0.1512(19) Uani 1.0 4 d . . . F11 F -0.2989(4) 0.0297(4) 0.2586(5) 0.157(2) Uani 1.0 4 d . . . O1 O 0.3499(4) 0.1449(3) 0.4702(5) 0.1109(16) Uani 1.0 4 d . . . O11 O 0.1396(4) 0.1835(4) 0.6500(4) 0.1123(16) Uani 1.0 4 d . . . C1 C 0.3062(6) 0.3040(4) 0.5558(7) 0.0981(19) Uani 1.0 4 d . . . C2 C 0.3785(6) 0.3873(4) 0.5012(7) 0.112(2) Uani 1.0 4 d . . . C3 C 0.3771(6) 0.2064(5) 0.5556(6) 0.0965(18) Uani 1.0 4 d . . . C4 C 0.4849(6) 0.1875(5) 0.6573(6) 0.0945(18) Uani 1.0 4 d . . . C5 C 0.5518(7) 0.1019(5) 0.6494(7) 0.115(3) Uani 1.0 4 d . . . C6 C 0.6530(7) 0.0786(6) 0.7394(8) 0.127(3) Uani 1.0 4 d . . . C7 C 0.6820(7) 0.1443(6) 0.8366(8) 0.116(3) Uani 1.0 4 d . . . C8 C 0.6187(7) 0.2297(6) 0.8514(7) 0.116(3) Uani 1.0 4 d . . . C9 C 0.5172(6) 0.2521(5) 0.7577(7) 0.109(2) Uani 1.0 4 d . . . C11 C 0.1778(5) 0.2918(4) 0.4826(7) 0.1002(19) Uani 1.0 4 d . . . C12 C 0.1045(7) 0.3901(5) 0.4816(8) 0.128(3) Uani 1.0 4 d . . . C13 C 0.1100(6) 0.2094(5) 0.5388(6) 0.0957(18) Uani 1.0 4 d . . . C14 C 0.0004(6) 0.1646(5) 0.4615(6) 0.0963(18) Uani 1.0 4 d . . . C15 C -0.0756(6) 0.1053(5) 0.5232(7) 0.106(2) Uani 1.0 4 d . . . C16 C -0.1771(6) 0.0586(5) 0.4547(8) 0.116(3) Uani 1.0 4 d . . . C17 C -0.1990(7) 0.0739(6) 0.3259(9) 0.122(3) Uani 1.0 4 d . . . C18 C -0.1272(7) 0.1318(7) 0.2606(8) 0.126(3) Uani 1.0 4 d . . . C19 C -0.0278(6) 0.1777(6) 0.3303(7) 0.113(2) Uani 1.0 4 d . . . H1A H 0.2999 0.3209 0.6448 0.1177 Uiso 1.0 4 calc R . . H2A H 0.3895 0.3703 0.4155 0.1340 Uiso 1.0 4 calc R . . H2B H 0.4562 0.3944 0.5537 0.1340 Uiso 1.0 4 calc R . . H2C H 0.3348 0.4494 0.5004 0.1340 Uiso 1.0 4 calc R . . H5A H 0.5288 0.0580 0.5816 0.1376 Uiso 1.0 4 calc R . . H6A H 0.6982 0.0207 0.7329 0.1523 Uiso 1.0 4 calc R . . H8A H 0.6413 0.2721 0.9209 0.1397 Uiso 1.0 4 calc R . . H9A H 0.4728 0.3103 0.7643 0.1305 Uiso 1.0 4 calc R . . H11A H 0.1840 0.2741 0.3938 0.1203 Uiso 1.0 4 calc R . . H12A H 0.0940 0.4069 0.5676 0.1532 Uiso 1.0 4 calc R . . H12B H 0.0265 0.3813 0.4301 0.1532 Uiso 1.0 4 calc R . . H12C H 0.1475 0.4431 0.4466 0.1532 Uiso 1.0 4 calc R . . H15A H -0.0584 0.0968 0.6115 0.1267 Uiso 1.0 4 calc R . . H16A H -0.2279 0.0185 0.4955 0.1389 Uiso 1.0 4 calc R . . H18A H -0.1450 0.1397 0.1722 0.1511 Uiso 1.0 4 calc R . . H19A H 0.0215 0.2184 0.2884 0.1357 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1 0.123(3) 0.170(4) 0.148(4) -0.004(3) -0.018(3) 0.030(3) F11 0.127(3) 0.163(4) 0.173(5) -0.026(3) -0.006(3) -0.040(3) O1 0.114(4) 0.107(3) 0.110(4) -0.003(3) 0.011(3) -0.016(3) O11 0.118(4) 0.124(4) 0.092(3) -0.011(3) 0.008(3) 0.000(3) C1 0.099(4) 0.097(4) 0.098(4) 0.003(3) 0.016(4) -0.003(3) C2 0.111(5) 0.093(4) 0.133(6) -0.002(3) 0.026(4) 0.002(4) C3 0.104(4) 0.092(4) 0.095(4) -0.001(3) 0.018(4) 0.002(3) C4 0.094(4) 0.093(4) 0.096(4) 0.002(3) 0.015(3) 0.001(3) C5 0.130(5) 0.101(4) 0.110(5) 0.009(4) 0.009(4) -0.007(4) C6 0.126(6) 0.122(5) 0.128(6) 0.025(5) 0.004(5) 0.009(5) C7 0.106(5) 0.118(5) 0.119(6) -0.003(4) 0.004(5) 0.009(5) C8 0.123(6) 0.127(6) 0.098(5) -0.024(5) 0.012(4) -0.004(4) C9 0.114(5) 0.103(4) 0.109(5) -0.005(4) 0.016(4) -0.014(4) C11 0.096(4) 0.100(4) 0.102(5) -0.002(3) 0.006(4) 0.009(3) C12 0.116(5) 0.099(5) 0.166(8) 0.007(4) 0.016(5) 0.012(5) C13 0.103(4) 0.099(4) 0.085(4) -0.003(3) 0.015(4) 0.001(3) C14 0.095(4) 0.098(4) 0.098(4) -0.006(3) 0.021(4) -0.006(3) C15 0.106(5) 0.103(4) 0.107(5) 0.001(4) 0.015(4) -0.003(4) C16 0.106(5) 0.108(5) 0.136(6) -0.005(4) 0.026(5) -0.008(5) C17 0.106(5) 0.119(5) 0.136(7) -0.004(4) 0.001(5) -0.030(5) C18 0.122(6) 0.146(6) 0.106(5) -0.020(5) 0.007(5) -0.015(5) C19 0.116(5) 0.123(5) 0.101(5) -0.010(4) 0.016(4) -0.008(4) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 F1 C7 1.356(8) yes . . F11 C17 1.361(9) yes . . O1 C3 1.223(8) yes . . O11 C13 1.221(8) yes . . C1 C2 1.536(9) yes . . C1 C3 1.524(8) yes . . C1 C11 1.528(8) yes . . C3 C4 1.506(8) yes . . C4 C5 1.373(9) yes . . C4 C9 1.371(9) yes . . C5 C6 1.396(10) yes . . C6 C7 1.352(11) yes . . C7 C8 1.361(11) yes . . C8 C9 1.416(10) yes . . C11 C12 1.544(9) yes . . C11 C13 1.507(9) yes . . C13 C14 1.487(8) yes . . C14 C15 1.392(9) yes . . C14 C19 1.385(10) yes . . C15 C16 1.394(9) yes . . C16 C17 1.361(13) yes . . C17 C18 1.372(12) yes . . C18 C19 1.378(10) yes . . C1 H1A 0.980 no . . C2 H2A 0.960 no . . C2 H2B 0.960 no . . C2 H2C 0.960 no . . C5 H5A 0.930 no . . C6 H6A 0.930 no . . C8 H8A 0.930 no . . C9 H9A 0.930 no . . C11 H11A 0.980 no . . C12 H12A 0.960 no . . C12 H12B 0.960 no . . C12 H12C 0.960 no . . C15 H15A 0.930 no . . C16 H16A 0.930 no . . C18 H18A 0.930 no . . C19 H19A 0.930 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C2 C1 C3 108.4(5) yes . . . C2 C1 C11 113.0(5) yes . . . C3 C1 C11 110.8(5) yes . . . O1 C3 C1 120.3(6) yes . . . O1 C3 C4 119.7(6) yes . . . C1 C3 C4 120.0(5) yes . . . C3 C4 C5 118.5(6) yes . . . C3 C4 C9 122.3(6) yes . . . C5 C4 C9 119.2(6) yes . . . C4 C5 C6 122.3(7) yes . . . C5 C6 C7 116.6(7) yes . . . F1 C7 C6 118.5(7) yes . . . F1 C7 C8 117.4(7) yes . . . C6 C7 C8 124.2(7) yes . . . C7 C8 C9 117.9(7) yes . . . C4 C9 C8 119.8(7) yes . . . C1 C11 C12 111.5(5) yes . . . C1 C11 C13 111.4(5) yes . . . C12 C11 C13 109.0(6) yes . . . O11 C13 C11 120.5(5) yes . . . O11 C13 C14 119.6(6) yes . . . C11 C13 C14 119.7(5) yes . . . C13 C14 C15 118.6(6) yes . . . C13 C14 C19 122.8(6) yes . . . C15 C14 C19 118.7(6) yes . . . C14 C15 C16 121.0(7) yes . . . C15 C16 C17 117.3(7) yes . . . F11 C17 C16 117.7(7) yes . . . F11 C17 C18 118.3(8) yes . . . C16 C17 C18 124.0(7) yes . . . C17 C18 C19 117.7(8) yes . . . C14 C19 C18 121.3(7) yes . . . C2 C1 H1A 108.164 no . . . C3 C1 H1A 108.169 no . . . C11 C1 H1A 108.162 no . . . C1 C2 H2A 109.475 no . . . C1 C2 H2B 109.473 no . . . C1 C2 H2C 109.472 no . . . H2A C2 H2B 109.467 no . . . H2A C2 H2C 109.465 no . . . H2B C2 H2C 109.476 no . . . C4 C5 H5A 118.874 no . . . C6 C5 H5A 118.871 no . . . C5 C6 H6A 121.688 no . . . C7 C6 H6A 121.685 no . . . C7 C8 H8A 121.031 no . . . C9 C8 H8A 121.032 no . . . C4 C9 H9A 120.124 no . . . C8 C9 H9A 120.116 no . . . C1 C11 H11A 108.257 no . . . C12 C11 H11A 108.260 no . . . C13 C11 H11A 108.258 no . . . C11 C12 H12A 109.468 no . . . C11 C12 H12B 109.467 no . . . C11 C12 H12C 109.468 no . . . H12A C12 H12B 109.471 no . . . H12A C12 H12C 109.480 no . . . H12B C12 H12C 109.474 no . . . C14 C15 H15A 119.504 no . . . C16 C15 H15A 119.513 no . . . C15 C16 H16A 121.327 no . . . C17 C16 H16A 121.329 no . . . C17 C18 H18A 121.144 no . . . C19 C18 H18A 121.148 no . . . C14 C19 H19A 119.329 no . . . C18 C19 H19A 119.327 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C2 C1 C3 O1 -99.5(7) no . . . . C2 C1 C3 C4 77.7(7) no . . . . C2 C1 C11 C12 -58.0(7) no . . . . C2 C1 C11 C13 179.9(5) no . . . . C3 C1 C11 C12 -179.9(5) no . . . . C3 C1 C11 C13 58.0(7) no . . . . C11 C1 C3 O1 25.1(9) no . . . . C11 C1 C3 C4 -157.8(5) no . . . . O1 C3 C4 C5 1.5(9) no . . . . O1 C3 C4 C9 -177.8(6) no . . . . C1 C3 C4 C5 -175.6(5) no . . . . C1 C3 C4 C9 5.1(9) no . . . . C3 C4 C5 C6 179.9(6) no . . . . C3 C4 C9 C8 179.2(6) no . . . . C5 C4 C9 C8 -0.0(10) no . . . . C9 C4 C5 C6 -0.7(10) no . . . . C4 C5 C6 C7 0.6(11) no . . . . C5 C6 C7 F1 -179.7(7) no . . . . C5 C6 C7 C8 0.5(12) no . . . . F1 C7 C8 C9 178.9(6) no . . . . C6 C7 C8 C9 -1.2(12) no . . . . C7 C8 C9 C4 1.0(11) no . . . . C1 C11 C13 O11 23.2(8) no . . . . C1 C11 C13 C14 -161.6(5) no . . . . C12 C11 C13 O11 -100.4(7) no . . . . C12 C11 C13 C14 74.9(7) no . . . . O11 C13 C14 C15 9.3(9) no . . . . O11 C13 C14 C19 -169.3(5) no . . . . C11 C13 C14 C15 -166.0(5) no . . . . C11 C13 C14 C19 15.4(9) no . . . . C13 C14 C15 C16 -177.6(5) no . . . . C13 C14 C19 C18 177.2(6) no . . . . C15 C14 C19 C18 -1.4(10) no . . . . C19 C14 C15 C16 1.0(9) no . . . . C14 C15 C16 C17 -0.4(9) no . . . . C15 C16 C17 F11 -179.0(6) no . . . . C15 C16 C17 C18 0.3(11) no . . . . F11 C17 C18 C19 178.7(6) no . . . . C16 C17 C18 C19 -0.7(12) no . . . . C17 C18 C19 C14 1.2(11) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 F1 C5 3.582(8) no . . F11 C15 3.593(8) no . . F11 C19 3.594(8) no . . O1 O11 3.276(7) no . . O1 C2 3.261(7) no . . O1 C5 2.770(8) no . . O1 C11 2.760(7) no . . O1 C13 3.002(8) no . . O11 C1 2.754(8) no . . O11 C3 2.984(8) no . . O11 C12 3.270(8) no . . O11 C15 2.767(7) no . . C1 C9 3.006(9) no . . C2 C4 3.261(8) no . . C2 C9 3.422(10) no . . C2 C12 3.029(10) no . . C3 C13 2.957(9) no . . C4 C7 2.735(9) no . . C5 C8 2.745(10) no . . C6 C9 2.788(11) no . . C11 C19 3.005(9) no . . C12 C14 3.219(9) no . . C12 C19 3.469(10) no . . C14 C17 2.736(10) no . . C15 C18 2.769(11) no . . C16 C19 2.774(11) no . . F1 C12 3.466(8) no . 2_646 F1 C12 3.580(8) no . 4_655 F1 C18 3.531(9) no . 1_656 F11 O11 3.414(7) no . 3_556 F11 C2 3.344(8) no . 2_545 F11 C5 3.578(9) no . 3_556 F11 C8 3.518(9) no . 4_454 F11 C9 3.559(9) no . 4_454 O1 C9 3.418(9) no . 4_554 O1 C16 3.488(9) no . 3_556 O11 F11 3.414(7) no . 3_556 O11 C11 3.490(8) no . 4_555 O11 C16 3.459(9) no . 3_556 O11 C17 3.498(9) no . 3_556 O11 C19 3.408(9) no . 4_555 C2 F11 3.344(8) no . 2_555 C5 F11 3.578(9) no . 3_556 C8 F11 3.518(9) no . 4_655 C8 C17 3.352(11) no . 4_655 C9 F11 3.559(9) no . 4_655 C9 O1 3.418(9) no . 4_555 C11 O11 3.490(8) no . 4_554 C12 F1 3.466(8) no . 2_656 C12 F1 3.580(8) no . 4_454 C15 C15 3.351(9) no . 3_556 C15 C16 3.546(9) no . 3_556 C16 O1 3.488(9) no . 3_556 C16 O11 3.459(9) no . 3_556 C16 C15 3.546(9) no . 3_556 C17 O11 3.498(9) no . 3_556 C17 C8 3.352(11) no . 4_454 C18 F1 3.531(9) no . 1_454 C19 O11 3.408(9) no . 4_554 F1 H6A 2.5181 no . . F1 H8A 2.4974 no . . F11 H16A 2.5113 no . . F11 H18A 2.5314 no . . O1 H1A 3.0893 no . . O1 H2A 3.1065 no . . O1 H2B 3.5971 no . . O1 H5A 2.4474 no . . O1 H11A 2.5669 no . . O11 H1A 2.5660 no . . O11 H11A 3.0721 no . . O11 H12A 3.1240 no . . O11 H15A 2.4700 no . . C1 H9A 2.6567 no . . C1 H12A 2.7542 no . . C1 H12B 3.3592 no . . C1 H12C 2.6986 no . . C2 H9A 2.9986 no . . C2 H11A 2.7420 no . . C2 H12A 3.3609 no . . C2 H12C 2.6574 no . . C3 H2A 2.6560 no . . C3 H2B 2.6591 no . . C3 H2C 3.3149 no . . C3 H5A 2.5908 no . . C3 H9A 2.6835 no . . C3 H11A 2.6926 no . . C4 H1A 2.7120 no . . C4 H2A 3.5746 no . . C4 H2B 2.9679 no . . C4 H6A 3.2652 no . . C4 H8A 3.2534 no . . C5 H9A 3.2099 no . . C6 H8A 3.2292 no . . C7 H5A 3.1773 no . . C7 H9A 3.2221 no . . C8 H6A 3.2347 no . . C9 H1A 2.6938 no . . C9 H2B 2.8748 no . . C9 H5A 3.2020 no . . C11 H2A 2.7709 no . . C11 H2B 3.3700 no . . C11 H2C 2.7229 no . . C11 H19A 2.6679 no . . C12 H1A 2.7240 no . . C12 H2A 3.3658 no . . C12 H2C 2.6642 no . . C12 H19A 3.1139 no . . C13 H1A 2.6884 no . . C13 H12A 2.6614 no . . C13 H12B 2.6680 no . . C13 H12C 3.3123 no . . C13 H15A 2.6093 no . . C13 H19A 2.6813 no . . C14 H11A 2.6976 no . . C14 H12A 3.5255 no . . C14 H12B 2.9287 no . . C14 H16A 3.2685 no . . C14 H18A 3.2503 no . . C15 H19A 3.2281 no . . C16 H18A 3.2454 no . . C17 H15A 3.1954 no . . C17 H19A 3.1949 no . . C18 H16A 3.2481 no . . C19 H11A 2.6816 no . . C19 H12B 2.9428 no . . C19 H15A 3.2279 no . . H1A H2A 2.8360 no . . H1A H2B 2.3319 no . . H1A H2C 2.3662 no . . H1A H9A 2.1412 no . . H1A H11A 2.8367 no . . H1A H12A 2.5842 no . . H1A H12C 2.9738 no . . H2A H11A 2.6056 no . . H2A H12C 2.9325 no . . H2B H9A 2.4728 no . . H2B H12C 3.5159 no . . H2C H9A 3.5032 no . . H2C H11A 2.9976 no . . H2C H12A 2.9348 no . . H2C H12B 3.5222 no . . H2C H12C 2.0798 no . . H5A H6A 2.3332 no . . H8A H9A 2.3622 no . . H11A H12A 2.8424 no . . H11A H12B 2.3413 no . . H11A H12C 2.3727 no . . H11A H19A 2.1119 no . . H12B H19A 2.6355 no . . H15A H16A 2.3357 no . . H18A H19A 2.3143 no . . F1 H2C 2.8306 no . 2_646 F1 H12A 3.2221 no . 2_646 F1 H12B 2.7418 no . 4_655 F1 H12C 2.8282 no . 2_646 F1 H18A 2.6176 no . 1_656 F11 H2A 2.8902 no . 2_545 F11 H2B 3.3701 no . 4_454 F11 H2C 2.9084 no . 2_545 F11 H5A 3.4788 no . 3_556 F11 H8A 3.2749 no . 4_454 F11 H9A 3.3289 no . 4_454 F11 H12C 3.1618 no . 2_545 O1 H1A 3.4281 no . 4_554 O1 H5A 3.1098 no . 3_656 O1 H6A 3.0691 no . 3_656 O1 H8A 3.5446 no . 4_554 O1 H9A 2.8062 no . 4_554 O1 H16A 2.6231 no . 3_556 O11 H11A 2.6099 no . 4_555 O11 H12B 3.4979 no . 4_555 O11 H12C 3.5489 no . 4_555 O11 H16A 3.3243 no . 3_556 O11 H19A 2.4843 no . 4_555 C2 H2B 3.5406 no . 3_666 C2 H6A 3.5378 no . 2_656 C3 H8A 3.4724 no . 4_554 C3 H9A 3.4146 no . 4_554 C3 H16A 3.4325 no . 3_556 C4 H2A 3.1693 no . 4_555 C4 H8A 3.3018 no . 4_554 C5 H2A 3.5865 no . 4_555 C5 H5A 3.2622 no . 3_656 C5 H8A 3.2224 no . 4_554 C5 H16A 3.3370 no . 1_655 C6 H2C 3.2290 no . 2_646 C6 H16A 3.1773 no . 1_655 C7 H2A 3.4913 no . 4_555 C7 H2C 3.1393 no . 2_646 C8 H2A 3.0480 no . 4_555 C8 H2B 3.4299 no . 4_555 C9 H2A 2.8623 no . 4_555 C12 H12A 3.4850 no . 3_566 C12 H12B 3.5653 no . 3_566 C13 H16A 3.3527 no . 3_556 C13 H19A 3.1064 no . 4_555 C14 H16A 3.5004 no . 3_556 C15 H8A 3.5723 no . 4_454 C15 H15A 3.4895 no . 3_556 C16 H6A 3.4741 no . 1_455 C16 H8A 3.0181 no . 4_454 C16 H15A 3.4984 no . 3_556 C17 H8A 2.9909 no . 4_454 C17 H12C 3.4872 no . 2_545 C18 H8A 3.5370 no . 4_454 C18 H12A 3.4689 no . 4_554 C18 H12C 3.3192 no . 2_545 C19 H12A 3.4593 no . 4_554 H1A O1 3.4281 no . 4_555 H1A H6A 2.9600 no . 2_656 H1A H11A 3.3511 no . 4_555 H2A F11 2.8902 no . 2_555 H2A C4 3.1693 no . 4_554 H2A C5 3.5865 no . 4_554 H2A C7 3.4913 no . 4_554 H2A C8 3.0480 no . 4_554 H2A C9 2.8623 no . 4_554 H2A H2B 3.5696 no . 3_666 H2A H8A 3.3821 no . 4_554 H2A H9A 3.1097 no . 4_554 H2B F11 3.3701 no . 4_655 H2B C2 3.5406 no . 3_666 H2B C8 3.4299 no . 4_554 H2B H2A 3.5696 no . 3_666 H2B H2B 3.2429 no . 3_666 H2B H2C 3.2405 no . 3_666 H2B H6A 3.4742 no . 2_656 H2B H8A 3.4690 no . 4_554 H2C F1 2.8306 no . 2_656 H2C F11 2.9084 no . 2_555 H2C C6 3.2290 no . 2_656 H2C C7 3.1393 no . 2_656 H2C H2B 3.2405 no . 3_666 H2C H6A 3.0485 no . 2_656 H5A F11 3.4788 no . 3_556 H5A O1 3.1098 no . 3_656 H5A C5 3.2622 no . 3_656 H5A H5A 2.3328 no . 3_656 H5A H8A 3.2007 no . 4_554 H5A H16A 3.0357 no . 1_655 H5A H16A 3.4823 no . 3_556 H6A O1 3.0691 no . 3_656 H6A C2 3.5378 no . 2_646 H6A C16 3.4741 no . 1_655 H6A H1A 2.9600 no . 2_646 H6A H2B 3.4742 no . 2_646 H6A H2C 3.0485 no . 2_646 H6A H9A 3.3948 no . 2_646 H6A H12A 3.2597 no . 2_646 H6A H15A 3.3314 no . 1_655 H6A H16A 2.7576 no . 1_655 H8A F11 3.2749 no . 4_655 H8A O1 3.5446 no . 4_555 H8A C3 3.4724 no . 4_555 H8A C4 3.3018 no . 4_555 H8A C5 3.2224 no . 4_555 H8A C15 3.5723 no . 4_655 H8A C16 3.0181 no . 4_655 H8A C17 2.9909 no . 4_655 H8A C18 3.5370 no . 4_655 H8A H2A 3.3821 no . 4_555 H8A H2B 3.4690 no . 4_555 H8A H5A 3.2007 no . 4_555 H8A H16A 3.1940 no . 4_655 H9A F11 3.3289 no . 4_655 H9A O1 2.8062 no . 4_555 H9A C3 3.4146 no . 4_555 H9A H2A 3.1097 no . 4_555 H9A H6A 3.3948 no . 2_656 H11A O11 2.6099 no . 4_554 H11A H1A 3.3511 no . 4_554 H12A F1 3.2221 no . 2_656 H12A C12 3.4850 no . 3_566 H12A C18 3.4689 no . 4_555 H12A C19 3.4593 no . 4_555 H12A H6A 3.2597 no . 2_656 H12A H12A 3.4179 no . 3_566 H12A H12B 3.1290 no . 3_566 H12A H12C 3.3385 no . 3_566 H12A H18A 3.0990 no . 4_555 H12A H19A 3.0759 no . 4_555 H12B F1 2.7418 no . 4_454 H12B O11 3.4979 no . 4_554 H12B C12 3.5653 no . 3_566 H12B H12A 3.1290 no . 3_566 H12B H12B 3.5797 no . 3_566 H12B H12C 3.4222 no . 3_566 H12B H15A 3.3674 no . 4_554 H12B H18A 3.4305 no . 4_555 H12C F1 2.8282 no . 2_656 H12C F11 3.1618 no . 2_555 H12C O11 3.5489 no . 4_554 H12C C17 3.4872 no . 2_555 H12C C18 3.3192 no . 2_555 H12C H12A 3.3385 no . 3_566 H12C H12B 3.4222 no . 3_566 H12C H18A 2.9047 no . 2_555 H15A C15 3.4895 no . 3_556 H15A C16 3.4984 no . 3_556 H15A H6A 3.3314 no . 1_455 H15A H12B 3.3674 no . 4_555 H15A H19A 3.1393 no . 4_555 H16A O1 2.6231 no . 3_556 H16A O11 3.3243 no . 3_556 H16A C3 3.4325 no . 3_556 H16A C5 3.3370 no . 1_455 H16A C6 3.1773 no . 1_455 H16A C13 3.3527 no . 3_556 H16A C14 3.5004 no . 3_556 H16A H5A 3.0357 no . 1_455 H16A H5A 3.4823 no . 3_556 H16A H6A 2.7576 no . 1_455 H16A H8A 3.1940 no . 4_454 H18A F1 2.6176 no . 1_454 H18A H12A 3.0990 no . 4_554 H18A H12B 3.4305 no . 4_554 H18A H12C 2.9047 no . 2_545 H19A O11 2.4843 no . 4_554 H19A C13 3.1064 no . 4_554 H19A H12A 3.0759 no . 4_554 H19A H15A 3.1393 no . 4_554 _database_code_depnum_ccdc_archive 'CCDC 969201'