# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_1 _audit_creation_date 2013-08-12T12:50:16-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H16 Br O4 P' _chemical_formula_sum 'C19 H16 Br O4 P' _chemical_formula_weight 419.2 _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 9.2741(10) _cell_length_b 38.324(4) _cell_length_c 5.0810(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1805.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9906 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 27.81 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.385 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_absorpt_correction_T_min 0.671 _exptl_absorpt_correction_T_max 0.888 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_av_R_equivalents 0.0931 _diffrn_reflns_av_unetI/netI 0.0827 _diffrn_reflns_number 28933 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -53 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 29.57 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.965 _reflns_number_total 4788 _reflns_number_gt 2963 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0796P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4788 _refine_ls_number_parameters 290 _refine_ls_number_restraints 133 _refine_ls_R_factor_all 0.1159 _refine_ls_R_factor_gt 0.0599 _refine_ls_wR_factor_ref 0.1583 _refine_ls_wR_factor_gt 0.1352 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 1932 Friedel Pairs' _refine_ls_abs_structure_Flack 0.02(2) _refine_diff_density_max 0.663 _refine_diff_density_min -0.707 _refine_diff_density_rms 0.085 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Br1 Br 0.25719(7) 0.202143(13) 0.50274(12) 0.0594(2) Uani 1 1 d . . . P1 P 0.40082(14) 0.37244(3) 0.9092(3) 0.0335(3) Uani 1 1 d D . . C1 C 0.3273(5) 0.33918(12) 1.1258(10) 0.0355(11) Uani 1 1 d . A . H1A H 0.3946 0.3353 1.2767 0.043 Uiso 1 1 calc R . . O1 O 0.1933(4) 0.35257(9) 1.2219(7) 0.0419(8) Uani 1 1 d . . . H1B H 0.2067 0.3625 1.3674 0.063 Uiso 1 1 calc R A . O2 O 0.3184(4) 0.37889(9) 0.6690(6) 0.0388(8) Uani 1 1 d . A . C11 C 0.3079(5) 0.30554(11) 0.9761(10) 0.0330(10) Uani 1 1 d . . . C12 C 0.1964(5) 0.30200(13) 0.7995(10) 0.0375(11) Uani 1 1 d . A . H12A H 0.1287 0.3204 0.777 0.045 Uiso 1 1 calc R . . C13 C 0.1831(6) 0.27140(13) 0.6539(11) 0.0446(13) Uani 1 1 d . . . H13A H 0.1089 0.2694 0.5261 0.054 Uiso 1 1 calc R A . C14 C 0.2765(5) 0.24423(12) 0.6938(9) 0.0368(11) Uani 1 1 d . A . C15 C 0.3888(6) 0.24748(13) 0.8756(11) 0.0434(12) Uani 1 1 d . . . H15A H 0.4546 0.2288 0.9029 0.052 Uiso 1 1 calc R A . C16 C 0.4026(5) 0.27814(11) 1.0145(11) 0.0401(11) Uani 1 1 d . A . H16A H 0.4785 0.2805 1.1388 0.048 Uiso 1 1 calc R . . O20 O 0.5601(4) 0.35847(9) 0.8735(8) 0.0491(10) Uani 1 1 d . A . C21 C 0.6793(5) 0.37785(12) 0.7850(10) 0.0337(11) Uani 1 1 d . . . C22 C 0.8089(6) 0.37085(14) 0.9064(12) 0.0471(13) Uani 1 1 d . A . H22A H 0.8159 0.3545 1.0462 0.057 Uiso 1 1 calc R . . C23 C 0.9282(6) 0.38873(17) 0.8153(15) 0.0610(18) Uani 1 1 d . . . H23A H 1.0196 0.3842 0.8924 0.073 Uiso 1 1 calc R A . C24 C 0.9185(7) 0.41282(16) 0.6172(15) 0.0646(18) Uani 1 1 d . A . H24A H 1.0017 0.4252 0.561 0.078 Uiso 1 1 calc R . . C25 C 0.7897(7) 0.41875(16) 0.5027(14) 0.0603(15) Uani 1 1 d . . . H25A H 0.7834 0.4353 0.364 0.072 Uiso 1 1 calc R A . C26 C 0.6664(6) 0.40140(14) 0.5817(12) 0.0484(14) Uani 1 1 d . A . H26A H 0.5762 0.4056 0.4989 0.058 Uiso 1 1 calc R . . O30 O 0.4127(13) 0.4072(3) 1.077(2) 0.031(3) Uani 0.5 1 d PDU A 1 C31 C 0.3282(13) 0.4386(3) 1.050(2) 0.036(3) Uani 0.5 1 d PDU A 1 C32 C 0.2759(11) 0.4529(3) 1.280(2) 0.051(2) Uani 0.5 1 d PDU A 1 H32 H 0.2914 0.4416 1.444 0.062 Uiso 0.5 1 calc PR A 1 C33 C 0.2005(12) 0.4840(3) 1.267(2) 0.057(3) Uani 0.5 1 d PDU A 1 H33 H 0.1659 0.4946 1.4237 0.069 Uiso 0.5 1 calc PR A 1 C34 C 0.1763(14) 0.4990(3) 1.032(2) 0.054(3) Uani 0.5 1 d PDU A 1 H34 H 0.1199 0.5197 1.0227 0.065 Uiso 0.5 1 calc PR A 1 C35 C 0.2315(13) 0.4851(3) 0.805(2) 0.054(2) Uani 0.5 1 d PDU A 1 H35 H 0.2193 0.4971 0.6432 0.064 Uiso 0.5 1 calc PR A 1 C36 C 0.3051(13) 0.4535(3) 0.810(2) 0.046(2) Uani 0.5 1 d PDU A 1 H36 H 0.3379 0.4427 0.6526 0.055 Uiso 0.5 1 calc PR A 1 O40 O 0.4388(13) 0.4056(3) 1.081(3) 0.041(4) Uani 0.5 1 d PU A 2 C41 C 0.3686(12) 0.4364(3) 1.053(2) 0.043(3) Uani 0.5 1 d PDU A 2 C42 C 0.4468(13) 0.4647(3) 0.979(3) 0.066(3) Uani 0.5 1 d PDU A 2 H42 H 0.5476 0.463 0.9484 0.079 Uiso 0.5 1 calc PR A 2 C43 C 0.3755(14) 0.4962(3) 0.949(3) 0.078(3) Uani 0.5 1 d PDU A 2 H43 H 0.43 0.516 0.8962 0.094 Uiso 0.5 1 calc PR A 2 C44 C 0.2319(14) 0.5004(3) 0.992(3) 0.061(3) Uani 0.5 1 d PDU A 2 H44 H 0.1865 0.5225 0.973 0.073 Uiso 0.5 1 calc PR A 2 C45 C 0.1547(13) 0.4708(3) 1.064(3) 0.058(3) Uani 0.5 1 d PDU A 2 H45 H 0.0536 0.4727 1.0894 0.069 Uiso 0.5 1 calc PR A 2 C46 C 0.2202(12) 0.4389(3) 1.098(3) 0.054(2) Uani 0.5 1 d PDU A 2 H46 H 0.166 0.4191 1.1519 0.064 Uiso 0.5 1 calc PR A 2 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 Br1 0.0821(4) 0.0415(3) 0.0546(3) -0.0100(3) 0.0095(4) -0.0139(3) P1 0.0340(6) 0.0354(6) 0.0312(6) -0.0030(5) -0.0002(6) -0.0030(5) C1 0.031(2) 0.045(3) 0.031(3) 0.000(2) 0.001(2) 0.000(2) O1 0.0388(19) 0.051(2) 0.0354(19) -0.0072(16) 0.0021(16) -0.0041(16) O2 0.048(2) 0.0454(19) 0.0231(17) -0.0059(14) -0.0045(15) -0.0041(16) C11 0.033(2) 0.038(2) 0.028(2) 0.003(2) 0.001(2) -0.0052(18) C12 0.035(3) 0.040(3) 0.038(3) 0.003(2) -0.007(2) -0.004(2) C13 0.044(3) 0.045(3) 0.045(3) 0.009(2) -0.009(3) -0.010(2) C14 0.043(3) 0.034(2) 0.034(2) -0.0015(19) 0.010(2) -0.008(2) C15 0.046(3) 0.038(3) 0.046(3) 0.005(2) 0.003(3) 0.000(2) C16 0.039(3) 0.042(2) 0.040(3) 0.000(2) 0.001(3) -0.003(2) O20 0.0340(19) 0.0401(18) 0.073(3) 0.011(2) 0.0092(18) -0.0019(15) C21 0.028(2) 0.033(2) 0.040(3) -0.007(2) 0.007(2) -0.003(2) C22 0.042(3) 0.051(3) 0.048(3) -0.001(3) -0.004(3) 0.014(3) C23 0.033(3) 0.068(4) 0.081(5) -0.010(4) -0.006(3) 0.012(3) C24 0.045(4) 0.070(4) 0.079(5) 0.000(4) 0.022(4) -0.011(3) C25 0.066(4) 0.062(3) 0.054(3) 0.013(3) 0.009(4) -0.010(3) C26 0.044(3) 0.057(3) 0.044(3) 0.008(3) -0.007(3) -0.001(3) O30 0.031(3) 0.032(3) 0.031(3) -0.0019(10) -0.0009(10) -0.0004(10) C31 0.036(3) 0.036(3) 0.035(3) -0.0002(10) -0.0002(10) 0.0001(10) C32 0.053(5) 0.055(5) 0.046(5) 0.002(5) 0.006(4) 0.007(5) C33 0.057(6) 0.055(5) 0.060(6) -0.012(5) 0.002(5) 0.014(5) C34 0.054(3) 0.053(3) 0.054(3) -0.0003(10) -0.0002(10) 0.0006(10) C35 0.073(6) 0.045(5) 0.043(5) 0.002(4) -0.022(5) 0.002(5) C36 0.065(5) 0.041(4) 0.032(4) 0.001(4) -0.016(4) 0.002(4) O40 0.040(4) 0.041(4) 0.040(4) -0.0018(10) -0.0011(10) -0.0006(10) C41 0.044(3) 0.043(3) 0.044(3) -0.0003(10) 0.0001(10) -0.0004(10) C42 0.055(5) 0.061(5) 0.080(6) -0.002(5) 0.000(5) -0.010(4) C43 0.078(3) 0.078(3) 0.079(3) 0.0000(10) 0.0002(10) -0.0009(10) C44 0.061(3) 0.060(3) 0.062(3) 0.0002(10) 0.0001(10) 0.0003(10) C45 0.056(5) 0.047(5) 0.070(6) 0.007(5) 0.002(5) 0.005(4) C46 0.053(6) 0.045(4) 0.063(5) 0.006(5) 0.012(5) 0.006(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Br1 C14 1.891(5) . ? P1 O2 1.461(4) . ? P1 O40 1.580(13) . ? P1 O20 1.581(4) . ? P1 O30 1.587(11) . ? P1 C1 1.817(5) . ? C1 O1 1.431(6) . ? C1 C11 1.507(6) . ? C1 H1A 1 . ? O1 H1B 0.84 . ? C11 C12 1.376(7) . ? C11 C16 1.383(6) . ? C12 C13 1.392(7) . ? C12 H12A 0.95 . ? C13 C14 1.369(7) . ? C13 H13A 0.95 . ? C14 C15 1.398(7) . ? C15 C16 1.377(7) . ? C15 H15A 0.95 . ? C16 H16A 0.95 . ? O20 C21 1.406(5) . ? C21 C26 1.377(7) . ? C21 C22 1.378(7) . ? C22 C23 1.381(8) . ? C22 H22A 0.95 . ? C23 C24 1.369(9) . ? C23 H23A 0.95 . ? C24 C25 1.349(9) . ? C24 H24A 0.95 . ? C25 C26 1.382(8) . ? C25 H25A 0.95 . ? C26 H26A 0.95 . ? O30 C31 1.443(17) . ? C31 C36 1.363(13) . ? C31 C32 1.378(13) . ? C32 C33 1.383(13) . ? C32 H32 0.95 . ? C33 C34 1.348(14) . ? C33 H33 0.95 . ? C34 C35 1.368(14) . ? C34 H34 0.95 . ? C35 C36 1.391(12) . ? C35 H35 0.95 . ? C36 H36 0.95 . ? O40 C41 1.357(18) . ? C41 C42 1.359(13) . ? C41 C46 1.398(13) . ? C42 C43 1.383(13) . ? C42 H42 0.95 . ? C43 C44 1.359(14) . ? C43 H43 0.95 . ? C44 C45 1.390(14) . ? C44 H44 0.95 . ? C45 C46 1.379(12) . ? C45 H45 0.95 . ? C46 H46 0.95 . ? 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 O2 P1 O40 116.2(5) . . ? O2 P1 O20 116.8(2) . . ? O40 P1 O20 97.3(5) . . ? O2 P1 O30 110.1(5) . . ? O40 P1 O30 9.1(7) . . ? O20 P1 O30 106.3(5) . . ? O2 P1 C1 115.4(2) . . ? O40 P1 C1 108.3(6) . . ? O20 P1 C1 100.5(2) . . ? O30 P1 C1 106.8(5) . . ? O1 C1 C11 112.1(4) . . ? O1 C1 P1 106.3(3) . . ? C11 C1 P1 109.8(3) . . ? O1 C1 H1A 109.5 . . ? C11 C1 H1A 109.5 . . ? P1 C1 H1A 109.5 . . ? C1 O1 H1B 109.5 . . ? C12 C11 C16 119.6(4) . . ? C12 C11 C1 120.2(4) . . ? C16 C11 C1 120.2(4) . . ? C11 C12 C13 119.7(5) . . ? C11 C12 H12A 120.1 . . ? C13 C12 H12A 120.1 . . ? C14 C13 C12 120.4(5) . . ? C14 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? C13 C14 C15 120.1(5) . . ? C13 C14 Br1 120.9(4) . . ? C15 C14 Br1 119.1(4) . . ? C16 C15 C14 119.0(5) . . ? C16 C15 H15A 120.5 . . ? C14 C15 H15A 120.5 . . ? C15 C16 C11 121.1(5) . . ? C15 C16 H16A 119.4 . . ? C11 C16 H16A 119.4 . . ? C21 O20 P1 126.3(3) . . ? C26 C21 C22 122.6(5) . . ? C26 C21 O20 121.2(5) . . ? C22 C21 O20 116.1(4) . . ? C21 C22 C23 116.9(5) . . ? C21 C22 H22A 121.6 . . ? C23 C22 H22A 121.6 . . ? C24 C23 C22 121.9(6) . . ? C24 C23 H23A 119 . . ? C22 C23 H23A 119 . . ? C25 C24 C23 119.3(6) . . ? C25 C24 H24A 120.4 . . ? C23 C24 H24A 120.4 . . ? C24 C25 C26 121.8(6) . . ? C24 C25 H25A 119.1 . . ? C26 C25 H25A 119.1 . . ? C21 C26 C25 117.5(6) . . ? C21 C26 H26A 121.3 . . ? C25 C26 H26A 121.3 . . ? C31 O30 P1 127.7(9) . . ? C36 C31 C32 122.6(11) . . ? C36 C31 O30 121.3(10) . . ? C32 C31 O30 116.1(10) . . ? C31 C32 C33 118.7(11) . . ? C31 C32 H32 120.7 . . ? C33 C32 H32 120.7 . . ? C34 C33 C32 119.6(11) . . ? C34 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? C33 C34 C35 121.2(11) . . ? C33 C34 H34 119.4 . . ? C35 C34 H34 119.4 . . ? C34 C35 C36 120.6(10) . . ? C34 C35 H35 119.7 . . ? C36 C35 H35 119.7 . . ? C31 C36 C35 117.2(10) . . ? C31 C36 H36 121.4 . . ? C35 C36 H36 121.4 . . ? C41 O40 P1 122.4(11) . . ? O40 C41 C42 117.9(11) . . ? O40 C41 C46 121.0(11) . . ? C42 C41 C46 121.2(12) . . ? C41 C42 C43 118.1(12) . . ? C41 C42 H42 120.9 . . ? C43 C42 H42 120.9 . . ? C44 C43 C42 123.7(13) . . ? C44 C43 H43 118.1 . . ? C42 C43 H43 118.1 . . ? C43 C44 C45 116.6(12) . . ? C43 C44 H44 121.7 . . ? C45 C44 H44 121.7 . . ? C46 C45 C44 122.2(11) . . ? C46 C45 H45 118.9 . . ? C44 C45 H45 118.9 . . ? C45 C46 C41 118.2(11) . . ? C45 C46 H46 120.9 . . ? C41 C46 H46 120.9 . . ? 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 O2 P1 C1 O1 -66.2(4) . . . . ? O40 P1 C1 O1 66.0(6) . . . . ? O20 P1 C1 O1 167.3(3) . . . . ? O30 P1 C1 O1 56.5(6) . . . . ? O2 P1 C1 C11 55.3(4) . . . . ? O40 P1 C1 C11 -172.6(5) . . . . ? O20 P1 C1 C11 -71.2(4) . . . . ? O30 P1 C1 C11 178.0(5) . . . . ? O1 C1 C11 C12 43.2(6) . . . . ? P1 C1 C11 C12 -74.7(5) . . . . ? O1 C1 C11 C16 -137.2(5) . . . . ? P1 C1 C11 C16 104.9(5) . . . . ? C16 C11 C12 C13 -2.4(7) . . . . ? C1 C11 C12 C13 177.2(5) . . . . ? C11 C12 C13 C14 2.9(8) . . . . ? C12 C13 C14 C15 -2.0(8) . . . . ? C12 C13 C14 Br1 178.6(4) . . . . ? C13 C14 C15 C16 0.7(8) . . . . ? Br1 C14 C15 C16 -180.0(4) . . . . ? C14 C15 C16 C11 -0.2(8) . . . . ? C12 C11 C16 C15 1.1(8) . . . . ? C1 C11 C16 C15 -178.5(5) . . . . ? O2 P1 O20 C21 72.8(5) . . . . ? O40 P1 O20 C21 -51.4(7) . . . . ? O30 P1 O20 C21 -50.4(6) . . . . ? C1 P1 O20 C21 -161.6(4) . . . . ? P1 O20 C21 C26 -40.5(7) . . . . ? P1 O20 C21 C22 141.9(4) . . . . ? C26 C21 C22 C23 0.1(8) . . . . ? O20 C21 C22 C23 177.7(5) . . . . ? C21 C22 C23 C24 1.2(9) . . . . ? C22 C23 C24 C25 -1.6(10) . . . . ? C23 C24 C25 C26 0.7(10) . . . . ? C22 C21 C26 C25 -1.0(8) . . . . ? O20 C21 C26 C25 -178.5(5) . . . . ? C24 C25 C26 C21 0.6(10) . . . . ? O2 P1 O30 C31 15.7(13) . . . . ? O40 P1 O30 C31 149(7) . . . . ? O20 P1 O30 C31 143.0(10) . . . . ? C1 P1 O30 C31 -110.3(11) . . . . ? P1 O30 C31 C36 -47.2(17) . . . . ? P1 O30 C31 C32 134.2(10) . . . . ? C36 C31 C32 C33 -1.8(14) . . . . ? O30 C31 C32 C33 176.8(11) . . . . ? C31 C32 C33 C34 1.9(14) . . . . ? C32 C33 C34 C35 -3.4(18) . . . . ? C33 C34 C35 C36 5(2) . . . . ? C32 C31 C36 C35 3.1(17) . . . . ? O30 C31 C36 C35 -175.4(11) . . . . ? C34 C35 C36 C31 -4.6(18) . . . . ? O2 P1 O40 C41 17.8(14) . . . . ? O20 P1 O40 C41 142.5(11) . . . . ? O30 P1 O40 C41 -32(5) . . . . ? C1 P1 O40 C41 -113.9(11) . . . . ? P1 O40 C41 C42 -118.6(12) . . . . ? P1 O40 C41 C46 61.0(17) . . . . ? O40 C41 C42 C43 179.6(13) . . . . ? C46 C41 C42 C43 0.0(14) . . . . ? C41 C42 C43 C44 0.4(16) . . . . ? C42 C43 C44 C45 -1(2) . . . . ? C43 C44 C45 C46 2(2) . . . . ? C44 C45 C46 C41 -2(2) . . . . ? O40 C41 C46 C45 -179.0(13) . . . . ? C42 C41 C46 C45 0.6(18) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 953498' ####################################################################### # # 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_1 _audit_creation_date 2013-05-15T20:04:21-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H16 Cl O4 P' _chemical_formula_sum 'C19 H16 Cl O4 P' _chemical_formula_weight 374.74 _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.2873(11) _cell_length_b 12.402(2) _cell_length_c 22.054(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1719.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9857 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 28.34 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prisms _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.336 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_absorpt_correction_T_min 0.835 _exptl_absorpt_correction_T_max 0.951 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_unetI/netI 0.0286 _diffrn_reflns_number 19889 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.57 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 0.955 _reflns_number_total 4095 _reflns_number_gt 3858 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0591P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_number_reflns 4095 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0883 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 1674 Friedel Pairs' _refine_ls_abs_structure_Flack -0.01(6) _refine_diff_density_max 0.301 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P1 P 0.04765(7) 0.81282(3) 0.762284(19) 0.01858(11) Uani 1 1 d . . . Cl1 Cl 0.15213(9) 0.91531(5) 0.49917(2) 0.03835(14) Uani 1 1 d . . . O1 O 0.1587(2) 1.00776(10) 0.73149(6) 0.0244(3) Uani 1 1 d . . . H11 H 0.119(6) 1.084(3) 0.7341(14) 0.072(9) Uiso 1 1 d . . . C1 C -0.0264(3) 0.94244(14) 0.72930(8) 0.0211(3) Uani 1 1 d . . . H1 H -0.141(3) 0.9682(16) 0.7548(9) 0.019(5) Uiso 1 1 d . . . O2 O -0.1225(2) 0.73203(10) 0.76829(6) 0.0221(3) Uani 1 1 d . . . C11 C -0.0267(3) 0.90032(15) 0.55912(8) 0.0265(4) Uani 1 1 d . . . C12 C 0.0388(3) 0.92974(14) 0.61691(8) 0.0228(3) Uani 1 1 d . . . H12 H 0.183(4) 0.9615(19) 0.6245(10) 0.029(6) Uiso 1 1 d . . . C13 C -0.1034(3) 0.91967(14) 0.66521(8) 0.0212(4) Uani 1 1 d . . . C14 C -0.3096(3) 0.88116(15) 0.65460(9) 0.0258(4) Uani 1 1 d . . . H14 H -0.401(5) 0.884(2) 0.6911(13) 0.063(9) Uiso 1 1 d . . . C15 C -0.3682(3) 0.85007(17) 0.59667(10) 0.0319(4) Uani 1 1 d . . . H15 H -0.509(4) 0.821(2) 0.5905(10) 0.035(6) Uiso 1 1 d . . . C16 C -0.2279(4) 0.85939(16) 0.54823(9) 0.0314(4) Uani 1 1 d . . . H16 H -0.266(4) 0.8347(18) 0.5072(10) 0.031(6) Uiso 1 1 d . . . O20 O 0.2422(2) 0.77398(10) 0.72174(6) 0.0223(3) Uani 1 1 d . . . C21 C 0.2510(3) 0.67910(14) 0.68685(7) 0.0193(3) Uani 1 1 d . . . C22 C 0.4386(3) 0.62107(15) 0.69082(8) 0.0232(4) Uani 1 1 d . . . H22 H 0.550(4) 0.6411(17) 0.7185(10) 0.025(5) Uiso 1 1 d . . . C23 C 0.4600(3) 0.52822(15) 0.65581(9) 0.0270(4) Uani 1 1 d . . . H23 H 0.591(4) 0.4842(19) 0.6570(11) 0.035(6) Uiso 1 1 d . . . C24 C 0.2951(3) 0.49472(16) 0.61845(9) 0.0273(4) Uani 1 1 d . . . H24 H 0.315(4) 0.4350(19) 0.5938(11) 0.034(6) Uiso 1 1 d . . . C25 C 0.1089(3) 0.55430(16) 0.61517(8) 0.0254(4) Uani 1 1 d . . . H25 H -0.013(4) 0.529(2) 0.5870(11) 0.040(7) Uiso 1 1 d . . . C26 C 0.0851(3) 0.64835(15) 0.64911(8) 0.0227(4) Uani 1 1 d . . . H26 H -0.042(4) 0.6892(17) 0.6483(9) 0.020(5) Uiso 1 1 d . . . O30 O 0.1551(2) 0.84851(10) 0.82384(5) 0.0227(3) Uani 1 1 d . . . C31 C 0.2318(3) 0.77117(14) 0.86584(8) 0.0222(4) Uani 1 1 d . . . C32 C 0.4363(3) 0.73076(16) 0.85853(9) 0.0292(4) Uani 1 1 d . . . H32 H 0.520(4) 0.7539(18) 0.8249(10) 0.028(6) Uiso 1 1 d . . . C33 C 0.5108(4) 0.65803(17) 0.90200(11) 0.0371(5) Uani 1 1 d . . . H33 H 0.666(4) 0.628(2) 0.8954(11) 0.045(7) Uiso 1 1 d . . . C34 C 0.3847(4) 0.62855(18) 0.95066(10) 0.0377(5) Uani 1 1 d . . . H34 H 0.429(4) 0.5815(18) 0.9801(10) 0.028(5) Uiso 1 1 d . . . C35 C 0.1824(4) 0.67069(18) 0.95663(9) 0.0370(5) Uani 1 1 d . . . H35 H 0.092(4) 0.648(2) 0.9905(12) 0.040(7) Uiso 1 1 d . . . C36 C 0.1039(3) 0.74269(16) 0.91372(9) 0.0291(4) Uani 1 1 d . . . H36 H -0.042(4) 0.7731(18) 0.9179(9) 0.025(5) Uiso 1 1 d . . . 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 P1 0.0188(2) 0.01490(19) 0.0220(2) -0.00014(16) 0.00086(17) 0.00031(17) Cl1 0.0406(3) 0.0511(3) 0.0234(2) 0.0021(2) 0.0046(2) 0.0062(3) O1 0.0234(6) 0.0168(6) 0.0331(7) -0.0004(5) -0.0006(6) -0.0021(5) C1 0.0203(8) 0.0165(7) 0.0266(8) -0.0003(6) 0.0016(7) 0.0008(7) O2 0.0210(6) 0.0193(6) 0.0258(6) 0.0009(5) 0.0013(5) -0.0005(5) C11 0.0302(10) 0.0240(9) 0.0253(8) 0.0031(7) -0.0002(8) 0.0033(8) C12 0.0248(9) 0.0186(8) 0.0250(8) 0.0025(6) 0.0011(7) -0.0002(8) C13 0.0220(8) 0.0162(8) 0.0252(8) 0.0026(7) 0.0008(7) 0.0034(7) C14 0.0231(9) 0.0226(9) 0.0317(9) 0.0049(7) -0.0002(7) 0.0015(7) C15 0.0255(10) 0.0284(10) 0.0419(11) 0.0068(8) -0.0082(9) -0.0029(9) C16 0.0375(11) 0.0263(10) 0.0304(10) 0.0002(8) -0.0110(8) 0.0029(9) O20 0.0186(6) 0.0190(6) 0.0292(6) -0.0043(5) 0.0027(5) -0.0001(5) C21 0.0222(8) 0.0157(7) 0.0200(8) 0.0001(6) 0.0012(6) -0.0003(7) C22 0.0198(8) 0.0229(8) 0.0269(9) 0.0006(7) 0.0001(7) 0.0003(7) C23 0.0233(9) 0.0255(9) 0.0320(9) -0.0015(7) 0.0034(8) 0.0037(9) C24 0.0340(11) 0.0228(9) 0.0252(9) -0.0041(7) 0.0056(8) 0.0015(8) C25 0.0275(9) 0.0270(9) 0.0217(8) -0.0003(7) -0.0016(7) -0.0037(8) C26 0.0228(9) 0.0218(9) 0.0235(8) 0.0034(6) -0.0002(7) 0.0034(7) O30 0.0266(6) 0.0170(6) 0.0245(6) -0.0006(5) -0.0018(5) -0.0009(5) C31 0.0261(9) 0.0173(8) 0.0231(8) -0.0011(6) -0.0048(7) -0.0023(7) C32 0.0283(10) 0.0254(9) 0.0339(10) -0.0042(7) -0.0033(8) 0.0013(8) C33 0.0345(12) 0.0303(11) 0.0465(12) -0.0066(9) -0.0139(9) 0.0070(9) C34 0.0524(14) 0.0257(10) 0.0351(11) 0.0024(8) -0.0177(10) -0.0006(10) C35 0.0496(13) 0.0330(11) 0.0283(9) 0.0047(8) -0.0027(9) -0.0045(11) C36 0.0318(11) 0.0278(10) 0.0277(9) -0.0013(7) 0.0007(8) -0.0025(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 P1 O2 1.4719(13) . ? P1 O30 1.5796(13) . ? P1 O20 1.5901(13) . ? P1 C1 1.8250(18) . ? Cl1 C11 1.746(2) . ? O1 C1 1.419(2) . ? O1 H11 0.99(3) . ? C1 C13 1.520(2) . ? C1 H1 0.97(2) . ? C11 C16 1.384(3) . ? C11 C12 1.388(3) . ? C12 C13 1.396(2) . ? C12 H12 1.00(2) . ? C13 C14 1.401(3) . ? C14 C15 1.385(3) . ? C14 H14 0.99(3) . ? C15 C16 1.390(3) . ? C15 H15 0.96(3) . ? C16 H16 0.99(2) . ? O20 C21 1.407(2) . ? C21 C22 1.385(3) . ? C21 C26 1.388(3) . ? C22 C23 1.393(3) . ? C22 H22 0.96(2) . ? C23 C24 1.388(3) . ? C23 H23 0.99(2) . ? C24 C25 1.386(3) . ? C24 H24 0.93(2) . ? C25 C26 1.394(3) . ? C25 H25 1.04(3) . ? C26 H26 0.95(2) . ? O30 C31 1.418(2) . ? C31 C36 1.373(3) . ? C31 C32 1.389(3) . ? C32 C33 1.397(3) . ? C32 H32 0.95(2) . ? C33 C34 1.384(4) . ? C33 H33 1.05(3) . ? C34 C35 1.382(4) . ? C34 H34 0.92(2) . ? C35 C36 1.391(3) . ? C35 H35 0.98(3) . ? C36 H36 1.00(2) . ? 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 O2 P1 O30 115.10(7) . . ? O2 P1 O20 113.82(7) . . ? O30 P1 O20 103.83(7) . . ? O2 P1 C1 116.74(8) . . ? O30 P1 C1 101.83(7) . . ? O20 P1 C1 103.83(8) . . ? C1 O1 H11 110(2) . . ? O1 C1 C13 113.51(14) . . ? O1 C1 P1 106.25(12) . . ? C13 C1 P1 106.76(12) . . ? O1 C1 H1 113.8(12) . . ? C13 C1 H1 111.3(12) . . ? P1 C1 H1 104.4(12) . . ? C16 C11 C12 121.80(19) . . ? C16 C11 Cl1 119.76(15) . . ? C12 C11 Cl1 118.44(16) . . ? C11 C12 C13 119.13(18) . . ? C11 C12 H12 121.6(13) . . ? C13 C12 H12 119.2(13) . . ? C12 C13 C14 119.70(17) . . ? C12 C13 C1 119.25(16) . . ? C14 C13 C1 120.87(16) . . ? C15 C14 C13 119.70(18) . . ? C15 C14 H14 127.4(18) . . ? C13 C14 H14 112.8(18) . . ? C14 C15 C16 121.12(19) . . ? C14 C15 H15 118.6(14) . . ? C16 C15 H15 120.3(14) . . ? C11 C16 C15 118.50(18) . . ? C11 C16 H16 119.7(14) . . ? C15 C16 H16 121.7(14) . . ? C21 O20 P1 126.22(11) . . ? C22 C21 C26 122.36(16) . . ? C22 C21 O20 115.68(15) . . ? C26 C21 O20 121.91(16) . . ? C21 C22 C23 118.50(17) . . ? C21 C22 H22 121.8(13) . . ? C23 C22 H22 119.6(13) . . ? C24 C23 C22 120.27(18) . . ? C24 C23 H23 118.2(14) . . ? C22 C23 H23 121.6(14) . . ? C25 C24 C23 120.16(18) . . ? C25 C24 H24 120.5(16) . . ? C23 C24 H24 119.2(16) . . ? C24 C25 C26 120.57(18) . . ? C24 C25 H25 119.6(14) . . ? C26 C25 H25 119.8(14) . . ? C21 C26 C25 118.13(17) . . ? C21 C26 H26 119.9(13) . . ? C25 C26 H26 121.9(13) . . ? C31 O30 P1 121.15(11) . . ? C36 C31 C32 122.55(18) . . ? C36 C31 O30 118.52(17) . . ? C32 C31 O30 118.87(17) . . ? C31 C32 C33 117.6(2) . . ? C31 C32 H32 119.6(14) . . ? C33 C32 H32 122.7(14) . . ? C34 C33 C32 120.7(2) . . ? C34 C33 H33 123.0(14) . . ? C32 C33 H33 116.3(14) . . ? C35 C34 C33 120.1(2) . . ? C35 C34 H34 116.8(15) . . ? C33 C34 H34 123.1(15) . . ? C34 C35 C36 120.3(2) . . ? C34 C35 H35 119.7(15) . . ? C36 C35 H35 120.0(16) . . ? C31 C36 C35 118.7(2) . . ? C31 C36 H36 120.8(13) . . ? C35 C36 H36 120.4(13) . . ? 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 O2 P1 C1 O1 176.74(10) . . . . ? O30 P1 C1 O1 50.52(12) . . . . ? O20 P1 C1 O1 -57.12(12) . . . . ? O2 P1 C1 C13 -61.82(14) . . . . ? O30 P1 C1 C13 171.96(12) . . . . ? O20 P1 C1 C13 64.32(13) . . . . ? C16 C11 C12 C13 -1.2(3) . . . . ? Cl1 C11 C12 C13 179.09(14) . . . . ? C11 C12 C13 C14 -0.6(3) . . . . ? C11 C12 C13 C1 174.69(17) . . . . ? O1 C1 C13 C12 21.3(2) . . . . ? P1 C1 C13 C12 -95.39(17) . . . . ? O1 C1 C13 C14 -163.47(16) . . . . ? P1 C1 C13 C14 79.81(18) . . . . ? C12 C13 C14 C15 2.1(3) . . . . ? C1 C13 C14 C15 -173.05(17) . . . . ? C13 C14 C15 C16 -2.0(3) . . . . ? C12 C11 C16 C15 1.4(3) . . . . ? Cl1 C11 C16 C15 -178.92(16) . . . . ? C14 C15 C16 C11 0.2(3) . . . . ? O2 P1 O20 C21 8.34(16) . . . . ? O30 P1 O20 C21 134.23(13) . . . . ? C1 P1 O20 C21 -119.62(14) . . . . ? P1 O20 C21 C22 -135.82(14) . . . . ? P1 O20 C21 C26 46.7(2) . . . . ? C26 C21 C22 C23 -0.4(3) . . . . ? O20 C21 C22 C23 -177.90(16) . . . . ? C21 C22 C23 C24 -0.7(3) . . . . ? C22 C23 C24 C25 0.8(3) . . . . ? C23 C24 C25 C26 0.1(3) . . . . ? C22 C21 C26 C25 1.3(3) . . . . ? O20 C21 C26 C25 178.67(16) . . . . ? C24 C25 C26 C21 -1.2(3) . . . . ? O2 P1 O30 C31 50.63(15) . . . . ? O20 P1 O30 C31 -74.44(14) . . . . ? C1 P1 O30 C31 177.91(14) . . . . ? P1 O30 C31 C36 -96.99(18) . . . . ? P1 O30 C31 C32 85.80(19) . . . . ? C36 C31 C32 C33 0.3(3) . . . . ? O30 C31 C32 C33 177.41(17) . . . . ? C31 C32 C33 C34 -0.5(3) . . . . ? C32 C33 C34 C35 0.2(3) . . . . ? C33 C34 C35 C36 0.2(3) . . . . ? C32 C31 C36 C35 0.1(3) . . . . ? O30 C31 C36 C35 -176.99(17) . . . . ? C34 C35 C36 C31 -0.4(3) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 953499'