# 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_mdeacn _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 171 _chemical_formula_moiety 'C7 H15 N2 O2, Cl' _chemical_formula_sum 'C7 H15 Cl N2 O2' _chemical_formula_weight 194.66 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' N N 0.0061 0.0033 '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 Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 10.363(2) _cell_length_b 12.708(3) _cell_length_c 13.781(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1814.8(6) _cell_formula_units_Z 8 _cell_measurement_temperature 298(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 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.384 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13514 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 26.21 _reflns_number_total 1812 _reflns_number_gt 1336 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.036(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1812 _refine_ls_number_parameters 117 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1559 _refine_ls_wR_factor_gt 0.1404 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _refine_ls_shift/su_max 0.000 _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 0.21468(7) 0.46569(6) 0.33178(5) 0.0507(3) Uani 1 1 d . . . O2 O 0.36555(18) 0.16579(15) 0.58124(14) 0.0481(5) Uani 1 1 d . . . O1 O 0.48453(17) 0.31126(15) 0.61867(15) 0.0468(5) Uani 1 1 d . . . N1 N 0.21806(19) 0.35322(16) 0.60765(15) 0.0377(5) Uani 1 1 d . . . N2 N 0.4531(2) 0.18380(19) 0.73639(18) 0.0476(6) Uani 1 1 d . . . H21 H 0.522(3) 0.142(3) 0.714(3) 0.057 Uiso 1 1 d . . . H22 H 0.402(3) 0.138(3) 0.766(3) 0.057 Uiso 1 1 d . . . C6 C 0.2717(2) 0.2914(2) 0.69105(18) 0.0378(5) Uani 1 1 d . . . H6A H 0.2096 0.2392 0.7122 0.045 Uiso 1 1 calc R . . H6B H 0.2901 0.3379 0.7451 0.045 Uiso 1 1 calc R . . C5 C 0.3076(3) 0.2156(2) 0.4983(2) 0.0496(7) Uani 1 1 d . . . H5A H 0.2839 0.1623 0.4511 0.060 Uiso 1 1 calc R . . H5B H 0.3699 0.2622 0.4681 0.060 Uiso 1 1 calc R . . C7 C 0.3947(2) 0.2379(2) 0.65757(19) 0.0397(6) Uani 1 1 d . . . C2 C 0.3152(3) 0.4365(2) 0.5773(2) 0.0448(6) Uani 1 1 d . . . H2A H 0.3247 0.4356 0.5073 0.054 Uiso 1 1 calc R . . H2B H 0.2835 0.5054 0.5960 0.054 Uiso 1 1 calc R . . C4 C 0.1902(3) 0.2771(2) 0.5262(2) 0.0458(6) Uani 1 1 d . . . H4A H 0.1227 0.2290 0.5463 0.055 Uiso 1 1 calc R . . H4B H 0.1592 0.3159 0.4702 0.055 Uiso 1 1 calc R . . C3 C 0.4445(3) 0.4174(2) 0.6241(2) 0.0483(6) Uani 1 1 d . . . H3A H 0.5086 0.4614 0.5925 0.058 Uiso 1 1 calc R . . H3B H 0.4402 0.4383 0.6917 0.058 Uiso 1 1 calc R . . C1 C 0.0944(3) 0.4046(2) 0.6372(2) 0.0517(7) Uani 1 1 d . . . H1A H 0.0333 0.3516 0.6560 0.077 Uiso 1 1 calc R . . H1B H 0.0605 0.4442 0.5837 0.077 Uiso 1 1 calc R . . H1C H 0.1101 0.4509 0.6910 0.077 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 0.0552(4) 0.0508(5) 0.0462(4) 0.0063(3) 0.0003(3) -0.0023(3) O2 0.0563(11) 0.0396(9) 0.0483(11) -0.0087(8) -0.0059(8) 0.0031(8) O1 0.0403(9) 0.0423(10) 0.0577(12) -0.0005(9) 0.0089(8) -0.0019(7) N1 0.0389(10) 0.0353(11) 0.0389(11) -0.0006(9) -0.0001(8) -0.0023(8) N2 0.0530(13) 0.0398(12) 0.0501(13) 0.0033(10) -0.0082(10) 0.0021(9) C6 0.0401(12) 0.0379(12) 0.0355(11) 0.0024(10) 0.0012(9) -0.0028(10) C5 0.0595(16) 0.0480(15) 0.0413(13) -0.0084(12) -0.0025(11) -0.0014(12) C7 0.0422(12) 0.0354(12) 0.0415(13) -0.0028(10) -0.0005(10) -0.0027(9) C2 0.0460(13) 0.0386(13) 0.0498(15) 0.0041(11) 0.0004(11) -0.0059(10) C4 0.0487(14) 0.0466(15) 0.0422(14) -0.0048(12) -0.0087(11) -0.0062(11) C3 0.0469(14) 0.0426(13) 0.0553(16) 0.0045(13) 0.0005(12) -0.0063(11) C1 0.0414(13) 0.0503(16) 0.0633(18) -0.0014(13) 0.0014(12) 0.0074(11) _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 O2 C7 1.427(3) . ? O2 C5 1.438(4) . ? O1 C3 1.413(3) . ? O1 C7 1.423(3) . ? N1 C1 1.495(3) . ? N1 C6 1.499(3) . ? N1 C4 1.509(3) . ? N1 C2 1.519(3) . ? N2 C7 1.421(3) . ? N2 H21 0.94(4) . ? N2 H22 0.89(4) . ? C6 C7 1.516(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C5 C4 1.497(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C2 C3 1.507(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? 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 C7 O2 C5 113.1(2) . . ? C3 O1 C7 114.47(19) . . ? C1 N1 C6 109.7(2) . . ? C1 N1 C4 108.6(2) . . ? C6 N1 C4 107.8(2) . . ? C1 N1 C2 109.8(2) . . ? C6 N1 C2 109.27(18) . . ? C4 N1 C2 111.6(2) . . ? C7 N2 H21 110(2) . . ? C7 N2 H22 115(2) . . ? H21 N2 H22 104(3) . . ? N1 C6 C7 108.28(19) . . ? N1 C6 H6A 110.0 . . ? C7 C6 H6A 110.0 . . ? N1 C6 H6B 110.0 . . ? C7 C6 H6B 110.0 . . ? H6A C6 H6B 108.4 . . ? O2 C5 C4 111.4(2) . . ? O2 C5 H5A 109.3 . . ? C4 C5 H5A 109.3 . . ? O2 C5 H5B 109.3 . . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? N2 C7 O1 109.0(2) . . ? N2 C7 O2 110.1(2) . . ? O1 C7 O2 106.4(2) . . ? N2 C7 C6 110.0(2) . . ? O1 C7 C6 111.7(2) . . ? O2 C7 C6 109.55(19) . . ? C3 C2 N1 111.1(2) . . ? C3 C2 H2A 109.4 . . ? N1 C2 H2A 109.4 . . ? C3 C2 H2B 109.4 . . ? N1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C5 C4 N1 111.7(2) . . ? C5 C4 H4A 109.3 . . ? N1 C4 H4A 109.3 . . ? C5 C4 H4B 109.3 . . ? N1 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? O1 C3 C2 113.1(2) . . ? O1 C3 H3A 109.0 . . ? C2 C3 H3A 109.0 . . ? O1 C3 H3B 109.0 . . ? C2 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.334 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 953755' ####################################################################### # # 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_teacn _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 168 _chemical_formula_moiety ? _chemical_formula_sum 'C8 H17 Cl N2 O3' _chemical_formula_weight 224.69 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' N N 0.0061 0.0033 '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 Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 12.111(2) _cell_length_b 12.998(3) _cell_length_c 12.998(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2045.9(7) _cell_formula_units_Z 8 _cell_measurement_temperature 298(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 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.359 _exptl_absorpt_correction_type none _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15605 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 26.54 _reflns_number_total 2057 _reflns_number_gt 1444 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1589P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2057 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1049 _refine_ls_R_factor_gt 0.0874 _refine_ls_wR_factor_ref 0.2170 _refine_ls_wR_factor_gt 0.1910 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.000 _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 -0.09617(8) -0.08259(7) 0.19390(8) 0.0648(4) Uani 1 1 d . . . O2 O 0.23056(17) 0.34109(18) -0.02651(17) 0.0517(6) Uani 1 1 d . . . O3 O 0.39102(17) 0.25481(17) -0.02638(18) 0.0511(6) Uani 1 1 d . . . N2 N 0.3842(2) 0.4239(2) 0.0294(2) 0.0505(6) Uani 1 1 d . . . H21 H 0.447(4) 0.419(3) 0.069(3) 0.061 Uiso 1 1 d . . . H22 H 0.394(3) 0.438(3) -0.039(4) 0.061 Uiso 1 1 d . . . N1 N 0.24325(19) 0.19548(19) 0.13482(19) 0.0436(6) Uani 1 1 d . . . C5 C 0.3091(2) 0.2923(2) 0.1384(2) 0.0455(7) Uani 1 1 d . . . H5A H 0.3791 0.2798 0.1723 0.055 Uiso 1 1 calc R . . H5B H 0.2694 0.3444 0.1769 0.055 Uiso 1 1 calc R . . C6 C 0.3287(2) 0.3291(2) 0.0284(2) 0.0456(7) Uani 1 1 d . . . C4 C 0.3377(3) 0.1574(3) -0.0321(3) 0.0528(7) Uani 1 1 d . . . H4A H 0.3860 0.1085 -0.0659 0.063 Uiso 1 1 calc R . . H4B H 0.2710 0.1637 -0.0729 0.063 Uiso 1 1 calc R . . O1 O 0.0449(3) 0.0972(2) 0.2712(3) 0.0754(8) Uani 1 1 d . . . H1 H 0.006(6) 0.040(5) 0.250(5) 0.113 Uiso 1 1 d . . . C7 C 0.2262(3) 0.1601(2) 0.2456(3) 0.0513(7) Uani 1 1 d . . . H7A H 0.2979 0.1458 0.2755 0.062 Uiso 1 1 calc R . . H7B H 0.1938 0.2164 0.2841 0.062 Uiso 1 1 calc R . . C8 C 0.1548(3) 0.0670(3) 0.2594(3) 0.0578(8) Uani 1 1 d . . . H8A H 0.1617 0.0223 0.1999 0.069 Uiso 1 1 calc R . . H8B H 0.1786 0.0289 0.3196 0.069 Uiso 1 1 calc R . . C2 C 0.1344(2) 0.3217(3) 0.0314(3) 0.0546(8) Uani 1 1 d . . . H2A H 0.0706 0.3270 -0.0134 0.066 Uiso 1 1 calc R . . H2B H 0.1274 0.3740 0.0843 0.066 Uiso 1 1 calc R . . C3 C 0.3081(3) 0.1175(2) 0.0748(3) 0.0514(7) Uani 1 1 d . . . H3A H 0.2651 0.0549 0.0683 0.062 Uiso 1 1 calc R . . H3B H 0.3753 0.1010 0.1119 0.062 Uiso 1 1 calc R . . C1 C 0.1344(2) 0.2174(3) 0.0816(3) 0.0511(7) Uani 1 1 d . . . H1A H 0.1210 0.1651 0.0298 0.061 Uiso 1 1 calc R . . H1B H 0.0750 0.2140 0.1315 0.061 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 0.0595(6) 0.0715(6) 0.0633(6) 0.0003(4) 0.0045(4) -0.0112(4) O2 0.0410(11) 0.0707(14) 0.0434(12) 0.0075(9) -0.0022(9) -0.0017(9) O3 0.0427(10) 0.0565(12) 0.0540(13) -0.0091(9) 0.0067(9) -0.0024(9) N2 0.0489(13) 0.0524(15) 0.0502(16) 0.0010(10) 0.0002(12) -0.0058(11) N1 0.0418(12) 0.0483(12) 0.0408(13) -0.0018(10) -0.0012(9) -0.0024(9) C5 0.0427(13) 0.0496(15) 0.0441(17) -0.0010(11) -0.0009(11) -0.0062(11) C6 0.0392(14) 0.0524(15) 0.0451(16) -0.0027(11) -0.0005(11) -0.0004(11) C4 0.0504(15) 0.0544(16) 0.0535(18) -0.0098(13) 0.0043(13) -0.0042(12) O1 0.0635(16) 0.0671(15) 0.096(2) -0.0124(14) 0.0183(15) -0.0138(12) C7 0.0567(16) 0.0548(16) 0.0423(16) 0.0018(12) -0.0016(13) -0.0060(13) C8 0.064(2) 0.0538(17) 0.055(2) 0.0011(13) 0.0034(16) -0.0100(14) C2 0.0383(15) 0.0670(19) 0.059(2) 0.0094(14) 0.0002(13) 0.0022(13) C3 0.0487(15) 0.0470(15) 0.059(2) -0.0068(13) 0.0002(14) 0.0030(12) C1 0.0378(14) 0.0646(18) 0.0510(17) 0.0037(13) -0.0055(12) -0.0011(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 O2 C6 1.395(3) . ? O2 C2 1.409(4) . ? O3 C6 1.418(4) . ? O3 C4 1.423(4) . ? N2 C6 1.404(4) . ? N2 H21 0.92(5) . ? N2 H22 0.91(5) . ? N1 C5 1.490(4) . ? N1 C3 1.501(4) . ? N1 C1 1.515(4) . ? N1 C7 1.525(4) . ? C5 C6 1.526(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C4 C3 1.526(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? O1 C8 1.396(5) . ? O1 H1 0.92(7) . ? C7 C8 1.498(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C2 C1 1.504(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? 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 C6 O2 C2 114.2(2) . . ? C6 O3 C4 112.9(2) . . ? C6 N2 H21 110(2) . . ? C6 N2 H22 103(3) . . ? H21 N2 H22 117(4) . . ? C5 N1 C3 107.8(2) . . ? C5 N1 C1 108.7(2) . . ? C3 N1 C1 110.2(2) . . ? C5 N1 C7 107.3(2) . . ? C3 N1 C7 111.0(2) . . ? C1 N1 C7 111.7(2) . . ? N1 C5 C6 108.6(2) . . ? N1 C5 H5A 110.0 . . ? C6 C5 H5A 110.0 . . ? N1 C5 H5B 110.0 . . ? C6 C5 H5B 110.0 . . ? H5A C5 H5B 108.3 . . ? O2 C6 N2 108.3(3) . . ? O2 C6 O3 105.8(2) . . ? N2 C6 O3 110.3(2) . . ? O2 C6 C5 112.5(2) . . ? N2 C6 C5 110.0(2) . . ? O3 C6 C5 109.9(2) . . ? O3 C4 C3 111.2(3) . . ? O3 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? O3 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C8 O1 H1 103(4) . . ? C8 C7 N1 115.8(3) . . ? C8 C7 H7A 108.3 . . ? N1 C7 H7A 108.3 . . ? C8 C7 H7B 108.3 . . ? N1 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? O1 C8 C7 109.6(3) . . ? O1 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? O1 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? O2 C2 C1 113.1(3) . . ? O2 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? O2 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? N1 C3 C4 111.5(3) . . ? N1 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? N1 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C2 C1 N1 111.5(2) . . ? C2 C1 H1A 109.3 . . ? N1 C1 H1A 109.3 . . ? C2 C1 H1B 109.3 . . ? N1 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? 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 O1 H1 Cl1 0.92(7) 2.15(7) 3.065(3) 175(6) . N2 H21 Cl1 0.92(5) 2.43(5) 3.342(3) 171(4) 8_665 N2 H22 Cl1 0.91(5) 2.76(4) 3.568(3) 148(3) 4 _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.323 _refine_diff_density_min -0.651 _refine_diff_density_rms 0.156 _database_code_depnum_ccdc_archive 'CCDC 953756' ####################################################################### # # 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_pf6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H15 F6 N2 O2 P' _chemical_formula_weight 304.18 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' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.8041(4) _cell_length_b 12.8542(6) _cell_length_c 10.0647(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.020(5) _cell_angle_gamma 90.00 _cell_volume 1139.02(12) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 16454 _cell_measurement_theta_min 2.02 _cell_measurement_theta_max 25.63 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.774 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.321 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9386 _exptl_absorpt_correction_T_max 0.9748 _exptl_absorpt_process_details 'XPREP in SHELXTL 6.14 (BrukerAXS Inc., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate ( 34 cm diameter )' _diffrn_detector_type STOE _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6228 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 25.11 _reflns_number_total 1998 _reflns_number_gt 1774 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0525P)^2^+0.2651P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1998 _refine_ls_number_parameters 169 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0871 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _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 C1 C 0.88047(15) 0.18050(12) 0.30903(14) 0.0285(3) Uani 1 1 d . . . H1A H 0.9435 0.2414 0.2847 0.034 Uiso 1 1 calc R . . H1B H 0.9494 0.1238 0.3372 0.034 Uiso 1 1 calc R . . C2 C 0.77731(16) 0.20917(12) 0.42254(14) 0.0283(3) Uani 1 1 d . . . H2A H 0.7245 0.1460 0.4548 0.034 Uiso 1 1 calc R . . H2B H 0.8388 0.2373 0.4967 0.034 Uiso 1 1 calc R . . C3 C 0.73634(16) 0.39111(11) 0.34069(14) 0.0297(3) Uani 1 1 d . . . H3A H 0.6842 0.4496 0.3855 0.036 Uiso 1 1 calc R . . H3B H 0.8437 0.3910 0.3699 0.036 Uiso 1 1 calc R . . C4 C 0.72930(17) 0.40666(12) 0.19130(15) 0.0325(3) Uani 1 1 d . . . H4A H 0.6247 0.4265 0.1655 0.039 Uiso 1 1 calc R . . H4B H 0.7981 0.4642 0.1657 0.039 Uiso 1 1 calc R . . C5 C 0.57637(14) 0.24522(11) 0.26544(13) 0.0257(3) Uani 1 1 d . . . H5A H 0.4979 0.2952 0.2356 0.031 Uiso 1 1 calc R . . H5B H 0.5254 0.1796 0.2913 0.031 Uiso 1 1 calc R . . C6 C 0.68897(15) 0.22479(11) 0.15385(13) 0.0265(3) Uani 1 1 d . . . C7 C 0.55399(18) 0.30585(13) 0.49428(14) 0.0345(4) Uani 1 1 d . . . H7A H 0.5067 0.2396 0.5188 0.052 Uiso 1 1 calc R . . H7B H 0.4751 0.3554 0.4676 0.052 Uiso 1 1 calc R . . H7C H 0.6099 0.3337 0.5706 0.052 Uiso 1 1 calc R . . N1 N 0.66147(12) 0.28889(9) 0.38095(11) 0.0237(3) Uani 1 1 d . . . N2 N 0.61021(16) 0.18893(12) 0.03970(14) 0.0390(3) Uani 1 1 d D . . H1N H 0.588(2) 0.1232(17) 0.052(2) 0.058 Uiso 1 1 d D . . H2N H 0.665(2) 0.1983(18) -0.029(2) 0.058 Uiso 1 1 d D . . O1 O 0.79474(11) 0.14754(8) 0.19594(10) 0.0284(2) Uani 1 1 d . . . O2 O 0.77206(11) 0.31453(8) 0.12184(10) 0.0302(3) Uani 1 1 d . . . P1 P 0.21966(4) 0.49208(3) 0.23096(4) 0.02932(16) Uani 1 1 d . . . F1 F 0.19930(13) 0.36874(8) 0.23705(10) 0.0515(3) Uani 1 1 d . . . F2 F 0.09604(15) 0.50443(9) 0.34571(12) 0.0596(4) Uani 1 1 d . . . F3 F 0.24122(11) 0.61488(8) 0.22782(10) 0.0442(3) Uani 1 1 d . . . F4 F 0.34363(12) 0.47869(9) 0.11771(11) 0.0494(3) Uani 1 1 d . . . F5 F 0.34995(14) 0.48387(9) 0.34039(12) 0.0596(4) Uani 1 1 d . . . F6 F 0.09092(12) 0.49977(9) 0.12243(12) 0.0567(3) Uani 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 C1 0.0243(6) 0.0298(8) 0.0313(7) 0.0005(6) -0.0033(5) 0.0038(6) C2 0.0293(7) 0.0290(7) 0.0267(7) 0.0041(6) -0.0017(6) 0.0005(6) C3 0.0318(7) 0.0222(8) 0.0352(8) -0.0024(6) 0.0037(6) -0.0047(6) C4 0.0361(8) 0.0240(7) 0.0375(8) 0.0055(6) 0.0075(6) 0.0023(6) C5 0.0214(6) 0.0278(7) 0.0279(7) -0.0029(6) -0.0012(5) -0.0018(5) C6 0.0253(7) 0.0281(7) 0.0259(7) -0.0026(5) -0.0010(5) 0.0042(6) C7 0.0333(8) 0.0431(9) 0.0272(7) -0.0031(6) 0.0104(6) 0.0000(7) N1 0.0232(5) 0.0252(6) 0.0226(6) -0.0010(4) 0.0026(4) -0.0016(4) N2 0.0389(7) 0.0482(9) 0.0298(7) -0.0116(6) -0.0068(6) 0.0070(6) O1 0.0280(5) 0.0262(5) 0.0310(5) -0.0040(4) -0.0012(4) 0.0055(4) O2 0.0320(5) 0.0306(6) 0.0279(5) 0.0034(4) 0.0090(4) 0.0041(4) P1 0.0291(3) 0.0299(3) 0.0290(3) -0.00112(14) -0.00113(18) 0.00138(14) F1 0.0711(7) 0.0319(6) 0.0515(6) -0.0021(4) 0.0093(5) -0.0077(5) F2 0.0674(8) 0.0573(7) 0.0543(7) 0.0007(5) 0.0296(6) 0.0070(5) F3 0.0440(5) 0.0303(5) 0.0584(6) 0.0009(4) -0.0032(5) 0.0027(4) F4 0.0431(6) 0.0514(6) 0.0536(7) -0.0100(5) 0.0165(5) -0.0054(5) F5 0.0705(8) 0.0500(7) 0.0581(7) -0.0090(5) -0.0346(6) 0.0172(5) F6 0.0416(6) 0.0727(8) 0.0558(7) 0.0068(5) -0.0194(5) -0.0091(5) _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 C1 O1 1.4297(17) . ? C1 C2 1.5056(19) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N1 1.5050(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.518(2) . ? C3 N1 1.5250(17) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O2 1.4258(18) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N1 1.4924(17) . ? C5 C6 1.5212(18) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 O2 1.4035(18) . ? C6 N2 1.4187(19) . ? C6 O1 1.4256(17) . ? C7 N1 1.4982(16) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? N2 H1N 0.88(2) . ? N2 H2N 0.85(2) . ? P1 F6 1.5769(11) . ? P1 F4 1.5877(10) . ? P1 F3 1.5902(10) . ? P1 F5 1.5934(11) . ? P1 F2 1.5952(11) . ? P1 F1 1.5967(11) . ? 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 O1 C1 C2 110.99(11) . . ? O1 C1 H1A 109.4 . . ? C2 C1 H1A 109.4 . . ? O1 C1 H1B 109.4 . . ? C2 C1 H1B 109.4 . . ? H1A C1 H1B 108.0 . . ? N1 C2 C1 111.38(11) . . ? N1 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? N1 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C4 C3 N1 111.04(11) . . ? C4 C3 H3A 109.4 . . ? N1 C3 H3A 109.4 . . ? C4 C3 H3B 109.4 . . ? N1 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? O2 C4 C3 111.45(12) . . ? O2 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? O2 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? N1 C5 C6 108.24(10) . . ? N1 C5 H5A 110.1 . . ? C6 C5 H5A 110.1 . . ? N1 C5 H5B 110.1 . . ? C6 C5 H5B 110.0 . . ? H5A C5 H5B 108.4 . . ? O2 C6 N2 109.62(12) . . ? O2 C6 O1 107.47(11) . . ? N2 C6 O1 109.48(12) . . ? O2 C6 C5 111.55(11) . . ? N2 C6 C5 109.61(11) . . ? O1 C6 C5 109.07(11) . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 N1 C7 109.32(10) . . ? C5 N1 C2 107.49(10) . . ? C7 N1 C2 108.39(11) . . ? C5 N1 C3 109.51(10) . . ? C7 N1 C3 110.49(11) . . ? C2 N1 C3 111.57(11) . . ? C6 N2 H1N 108.1(14) . . ? C6 N2 H2N 109.7(15) . . ? H1N N2 H2N 112(2) . . ? C6 O1 C1 112.01(10) . . ? C6 O2 C4 115.62(10) . . ? F6 P1 F4 90.21(6) . . ? F6 P1 F3 90.56(6) . . ? F4 P1 F3 90.65(6) . . ? F6 P1 F5 179.77(7) . . ? F4 P1 F5 89.66(7) . . ? F3 P1 F5 89.63(6) . . ? F6 P1 F2 90.28(7) . . ? F4 P1 F2 179.31(7) . . ? F3 P1 F2 89.83(6) . . ? F5 P1 F2 89.85(7) . . ? F6 P1 F1 90.47(6) . . ? F4 P1 F1 89.84(6) . . ? F3 P1 F1 178.86(6) . . ? F5 P1 F1 89.34(6) . . ? F2 P1 F1 89.68(6) . . ? 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 N2 H1N F2 0.88(2) 2.46(2) 3.202(2) 143.6(19) 2_545 N2 H2N F1 0.85(2) 2.53(2) 3.2318(17) 141.1(19) 4_665 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.223 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 953757' ####################################################################### # # 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_mdpf6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H15 F6 N2 O2 P' _chemical_formula_weight 304.18 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' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _chemical_absolute_configuration unk loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.3381(13) _cell_length_b 8.1858(16) _cell_length_c 11.115(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.48(3) _cell_angle_gamma 90.00 _cell_volume 567.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6271 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 25.50 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.782 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.322 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9384 _exptl_absorpt_correction_T_max 0.9563 _exptl_absorpt_process_details 'XPREP in SHELXTL 6.14 (BrukerAXS Inc., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate ( 34 cm diameter )' _diffrn_detector_type STOE _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2908 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.14 _reflns_number_total 1745 _reflns_number_gt 1559 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0754P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(15) _refine_ls_number_reflns 1745 _refine_ls_number_parameters 163 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.1058 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.000 _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 P1 P 0.36941(12) 0.01790(11) 0.78969(7) 0.0283(2) Uani 1 1 d . . . F1 F 0.2931(4) 0.1401(3) 0.6801(2) 0.0588(7) Uani 1 1 d . . . F2 F 0.2760(3) -0.1341(3) 0.7080(2) 0.0462(6) Uani 1 1 d . . . F3 F 0.1461(3) 0.0378(3) 0.8334(2) 0.0523(6) Uani 1 1 d . . . F4 F 0.5940(3) -0.0043(3) 0.7483(2) 0.0565(7) Uani 1 1 d . . . F5 F 0.4462(4) -0.1032(3) 0.9033(2) 0.0560(7) Uani 1 1 d . . . F6 F 0.4691(4) 0.1670(3) 0.8740(3) 0.0630(8) Uani 1 1 d . . . N1 N 0.7672(3) 0.5245(4) 0.7380(2) 0.0237(5) Uani 1 1 d . . . N2 N 0.2608(3) 0.4459(3) 0.5344(2) 0.0244(5) Uani 1 1 d D . . H2 H 0.2238 0.5301 0.5472 0.037 Uiso 1 1 d RD . . O1 O 0.5689(3) 0.3254(3) 0.5350(2) 0.0341(6) Uani 1 1 d . . . O2 O 1.1810(4) 0.4828(5) 0.9136(3) 0.0623(9) Uani 1 1 d . . . H2C H 1.3092 0.5093 0.9397 0.093 Uiso 1 1 calc R . . C1 C 0.7960(5) 0.3083(5) 0.5851(3) 0.0362(8) Uani 1 1 d . . . H1A H 0.8791 0.3778 0.5376 0.043 Uiso 1 1 calc R . . H1B H 0.8394 0.1935 0.5760 0.043 Uiso 1 1 calc R . . C2 C 0.8497(5) 0.3556(4) 0.7179(3) 0.0289(7) Uani 1 1 d . . . H2A H 1.0072 0.3528 0.7454 0.035 Uiso 1 1 calc R . . H2B H 0.7850 0.2758 0.7674 0.035 Uiso 1 1 calc R . . C3 C 0.5277(4) 0.5159(5) 0.7006(3) 0.0321(7) Uani 1 1 d . . . H3A H 0.4707 0.6287 0.6944 0.038 Uiso 1 1 calc R . . H3B H 0.4691 0.4604 0.7665 0.038 Uiso 1 1 calc R . . C4 C 0.4449(5) 0.4293(4) 0.5823(3) 0.0297(7) Uani 1 1 d . . . C5 C 0.8536(5) 0.6508(4) 0.6618(3) 0.0349(8) Uani 1 1 d . . . H5A H 1.0099 0.6573 0.6864 0.052 Uiso 1 1 calc R . . H5B H 0.7901 0.7573 0.6741 0.052 Uiso 1 1 calc R . . H5C H 0.8171 0.6204 0.5753 0.052 Uiso 1 1 calc R . . C6 C 0.8147(5) 0.5697(5) 0.8729(3) 0.0352(8) Uani 1 1 d . . . H6A H 0.7769 0.4756 0.9208 0.042 Uiso 1 1 calc R . . H6B H 0.7205 0.6619 0.8863 0.042 Uiso 1 1 calc R . . C7 C 1.0465(6) 0.6177(5) 0.9228(3) 0.0418(9) Uani 1 1 d . . . H7A H 1.0885 0.7108 0.8754 0.050 Uiso 1 1 calc R . . H7B H 1.0612 0.6518 1.0093 0.050 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 P1 0.0332(4) 0.0245(4) 0.0272(4) 0.0005(4) 0.0058(3) 0.0000(3) F1 0.0738(15) 0.0494(16) 0.0522(16) 0.0262(14) 0.0090(12) 0.0029(12) F2 0.0527(12) 0.0403(14) 0.0464(13) -0.0144(12) 0.0113(10) -0.0124(10) F3 0.0457(11) 0.0619(16) 0.0543(14) 0.0034(14) 0.0219(9) 0.0094(11) F4 0.0402(11) 0.0540(16) 0.0815(17) -0.0122(14) 0.0282(11) -0.0073(11) F5 0.0577(13) 0.0608(17) 0.0431(15) 0.0185(13) -0.0078(11) -0.0006(11) F6 0.0836(18) 0.0435(16) 0.0627(18) -0.0240(14) 0.0153(13) -0.0177(12) N1 0.0262(11) 0.0243(13) 0.0206(12) 0.0020(13) 0.0045(9) 0.0027(11) N2 0.0159(11) 0.0240(13) 0.0302(14) 0.0064(12) -0.0036(9) 0.0027(9) O1 0.0292(10) 0.0444(15) 0.0275(12) -0.0081(11) 0.0020(9) -0.0042(9) O2 0.0420(14) 0.083(3) 0.0520(17) -0.0187(17) -0.0172(12) 0.0091(14) C1 0.0263(15) 0.041(2) 0.041(2) -0.0135(17) 0.0035(13) -0.0006(13) C2 0.0276(14) 0.0226(16) 0.0350(18) -0.0010(15) 0.0018(12) 0.0002(12) C3 0.0256(14) 0.0304(16) 0.0397(18) -0.0023(19) 0.0045(12) -0.0005(15) C4 0.0327(16) 0.0287(18) 0.0282(17) 0.0062(15) 0.0066(13) -0.0019(14) C5 0.0409(17) 0.031(2) 0.0333(19) 0.0074(16) 0.0087(14) -0.0049(14) C6 0.0439(18) 0.042(2) 0.0219(17) -0.0082(15) 0.0104(13) -0.0062(14) C7 0.0453(19) 0.052(2) 0.0260(18) -0.0063(18) 0.0021(14) -0.0106(17) _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 F1 1.582(3) . ? P1 F4 1.584(2) . ? P1 F3 1.586(2) . ? P1 F2 1.590(2) . ? P1 F6 1.597(2) . ? P1 F5 1.610(2) . ? N1 C3 1.500(3) . ? N1 C5 1.502(4) . ? N1 C2 1.509(4) . ? N1 C6 1.521(4) . ? N2 C4 1.199(4) . ? N2 H2 0.7500 . ? O1 C4 1.329(4) . ? O1 C1 1.452(4) . ? O2 C7 1.410(5) . ? O2 H2C 0.8400 . ? C1 C2 1.504(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.502(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.524(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? 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 F1 P1 F4 90.79(14) . . ? F1 P1 F3 90.33(13) . . ? F4 P1 F3 178.88(16) . . ? F1 P1 F2 91.45(14) . . ? F4 P1 F2 90.30(13) . . ? F3 P1 F2 89.72(13) . . ? F1 P1 F6 90.07(16) . . ? F4 P1 F6 88.72(14) . . ? F3 P1 F6 91.24(15) . . ? F2 P1 F6 178.20(16) . . ? F1 P1 F5 178.67(17) . . ? F4 P1 F5 89.89(14) . . ? F3 P1 F5 88.99(13) . . ? F2 P1 F5 89.69(14) . . ? F6 P1 F5 88.80(15) . . ? C3 N1 C5 109.3(2) . . ? C3 N1 C2 106.0(3) . . ? C5 N1 C2 112.1(2) . . ? C3 N1 C6 107.1(2) . . ? C5 N1 C6 111.2(3) . . ? C2 N1 C6 110.9(3) . . ? C4 N2 H2 109.5 . . ? C4 O1 C1 121.7(3) . . ? C7 O2 H2C 109.5 . . ? O1 C1 C2 112.5(2) . . ? O1 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? O1 C1 H1B 109.1 . . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? C1 C2 N1 111.0(3) . . ? C1 C2 H2A 109.4 . . ? N1 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? N1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? N1 C3 C4 116.1(3) . . ? N1 C3 H3A 108.3 . . ? C4 C3 H3A 108.3 . . ? N1 C3 H3B 108.3 . . ? C4 C3 H3B 108.3 . . ? H3A C3 H3B 107.4 . . ? N2 C4 O1 119.7(3) . . ? N2 C4 C3 119.5(3) . . ? O1 C4 C3 120.7(3) . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 C7 115.2(2) . . ? N1 C6 H6A 108.5 . . ? C7 C6 H6A 108.5 . . ? N1 C6 H6B 108.5 . . ? C7 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? O2 C7 C6 109.1(3) . . ? O2 C7 H7A 109.9 . . ? C6 C7 H7A 109.9 . . ? O2 C7 H7B 109.9 . . ? C6 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? 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 O2 H2C F5 0.84 2.30 2.910(4) 129.4 2_757 O2 H2C F6 0.84 2.62 3.295(4) 138.2 2_757 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.282 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 953758'