# Electronic Supplementary Material (ESI) for Chemical Communications # 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 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H3 Fe O4 P' _chemical_formula_structural ? _chemical_formula_sum 'C4 H3 Fe O4 P' _chemical_formula_iupac ? _chemical_formula_weight 201.88 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall 'C -2yc' _symmetry_space_group_name_H-M 'C c' _symmetry_Int_Tables_number 9 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 x,-y,1/2+z 3 1/2+x,1/2+y,z 4 1/2+x,1/2-y,1/2+z _cell_length_a 11.7363(11) _cell_length_b 6.9251(7) _cell_length_c 9.3352(11) _cell_angle_alpha 90 _cell_angle_beta 105.518(11) _cell_angle_gamma 90 _cell_volume 731.06(14) _cell_formula_units_Z 4 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 1147 _cell_measurement_theta_min 3.5961 _cell_measurement_theta_max 29.6355 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3501 _exptl_crystal_size_mid 0.1489 _exptl_crystal_size_min 0.1283 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.834 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 2.224 _exptl_absorpt_correction_T_min 0.646 _exptl_absorpt_correction_T_max 0.809 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_density_meas_temp ? #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini Ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5431 # number of measured reflections (redundant set) _diffrn_reflns_number 1971 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 27.10 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1357 # number of observed reflections (> n sig(I)) _reflns_number_gt 1153 _reflns_threshold_expression >2\s(i) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs 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^)+(0.0469P)^2^] 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 refall _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(3) _chemical_absolute_configuration ad _refine_ls_number_reflns 1357 _refine_ls_number_parameters 103 _refine_ls_number_restraints 2 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.0931 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.100 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.466 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.082 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Fe1 Fe Uani 0.87490 0.16715(8) 0.06460 1.000 0.0174(2) . . P P Uani 1.03365(15) 0.1655(3) -0.02179(19) 1.000 0.0206(5) . . O1 O Uani 0.6697(4) 0.1667(6) 0.1846(5) 1.000 0.0330(17) . . O2 O Uani 0.7462(5) 0.3941(9) -0.1953(6) 1.000 0.0354(17) . . O3 O Uani 1.0153(4) 0.3775(10) 0.3271(6) 1.000 0.0328(18) . . O4 O Uani 0.8676(7) -0.2560(5) 0.0456(8) 1.000 0.0390(18) . . C1 C Uani 0.7493(5) 0.1664(10) 0.1394(7) 1.000 0.0194(17) . . C2 C Uani 0.7989(6) 0.3058(10) -0.0931(8) 1.000 0.020(2) . . C3 C Uani 0.9615(7) 0.2963(10) 0.2254(9) 1.000 0.027(3) . . C4 C Uani 0.8707(8) -0.0899(7) 0.0515(9) 1.000 0.0239(16) . . H1 H Uiso 1.116(5) 0.308(8) 0.025(7) 1.000 0.021(14) . . H2 H Uiso 1.119(5) 0.018(8) 0.012(6) 1.000 0.020(13) . . H3 H Uiso 1.031(6) 0.176(9) -0.161(8) 1.000 0.040(18) . . 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 Fe1 0.0173(4) 0.0177(3) 0.0186(4) 0.0001(8) 0.0070(3) -0.0002(7) P 0.0186(9) 0.0254(10) 0.0190(9) 0.0011(9) 0.0072(8) -0.0006(9) O1 0.037(3) 0.033(3) 0.037(3) -0.003(2) 0.024(2) -0.001(2) O2 0.037(3) 0.040(3) 0.032(3) 0.009(3) 0.014(3) 0.006(3) O3 0.020(2) 0.052(4) 0.021(3) -0.016(3) -0.004(2) -0.011(2) O4 0.053(3) 0.0174(17) 0.055(4) -0.003(3) 0.029(3) -0.003(3) C1 0.016(3) 0.016(3) 0.021(3) 0.002(3) -0.004(3) 0.002(2) C2 0.014(3) 0.027(4) 0.018(4) 0.003(3) 0.003(3) 0.001(3) C3 0.033(4) 0.025(4) 0.032(5) 0.015(3) 0.024(4) 0.006(3) C4 0.027(3) 0.026(2) 0.024(3) -0.004(4) 0.016(2) -0.005(4) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 P 2.2194(18) . . yes Fe1 C1 1.792(6) . . yes Fe1 C2 1.784(7) . . yes Fe1 C3 1.808(8) . . yes Fe1 C4 1.784(5) . . yes P H3 1.29(7) . . no P H1 1.37(6) . . no P H2 1.41(6) . . no O1 C1 1.123(8) . . yes O2 C2 1.162(9) . . yes O3 C3 1.138(10) . . yes O4 C4 1.152(6) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P Fe1 C1 178.4(2) . . . yes P Fe1 C2 89.2(2) . . . yes P Fe1 C3 88.0(3) . . . yes P Fe1 C4 88.9(3) . . . yes C1 Fe1 C2 92.4(3) . . . yes C1 Fe1 C3 90.9(3) . . . yes C1 Fe1 C4 90.8(4) . . . yes C2 Fe1 C3 117.7(3) . . . yes C2 Fe1 C4 118.8(3) . . . yes C3 Fe1 C4 123.3(4) . . . yes H1 P H2 93(3) . . . no H1 P H3 96(4) . . . no H2 P H3 95(4) . . . no Fe1 P H3 125(3) . . . no Fe1 P H1 118(3) . . . no Fe1 P H2 123(2) . . . no Fe1 C1 O1 179.1(6) . . . yes Fe1 C2 O2 178.0(7) . . . yes Fe1 C3 O3 179.5(7) . . . yes Fe1 C4 O4 178.7(8) . . . yes loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag P C2 2.828(8) . . no P C3 2.812(8) . . no P C4 2.820(8) . . no P O3 3.448(7) . 2_564 no P O2 3.408(6) . 4_555 no O1 O3 3.218(7) . 3_445 no O2 C1 3.417(9) . 2_564 no O2 P 3.408(6) . 4_454 no O3 O4 3.125(9) . 2_555 no O3 P 3.448(7) . 2_565 no O3 O1 3.218(7) . 3_555 no O4 O3 3.125(9) . 2_554 no O4 C2 3.313(8) . 1_545 no O1 H3 2.68(7) . 4_455 no O1 H2 2.89(6) . 3_455 no O1 H1 2.88(6) . 3_445 no O2 H2 2.81(5) . 4_454 no O2 H2 2.87(6) . 3_455 no O3 H1 2.90(6) . 2_565 no C1 C2 2.580(10) . . no C1 C3 2.566(10) . . no C1 C4 2.545(10) . . no C1 O2 3.417(9) . 2_565 no C2 O4 3.313(8) . 1_565 no C2 C1 2.580(10) . . no C2 P 2.828(8) . . no C2 C4 3.071(9) . . no C2 C3 3.074(11) . . no C3 C1 2.566(10) . . no C3 P 2.812(8) . . no C3 C2 3.074(11) . . no C3 C4 3.162(9) . . no C4 C2 3.071(9) . . no C4 P 2.820(8) . . no C4 C3 3.162(9) . . no C4 C1 2.545(10) . . no C1 H2 2.95(6) . 3_455 no C1 H1 2.98(6) . 3_445 no C2 H2 2.95(6) . 3_455 no C2 H3 3.09(7) . . no C3 H1 2.93(6) . . no C4 H3 2.90(7) . 2_555 no C4 H1 3.02(6) . 3_445 no H1 O3 2.90(6) . 2_564 no H1 O1 2.88(6) . 3_555 no H1 C1 2.98(6) . 3_555 no H1 C4 3.02(6) . 3_555 no H2 O1 2.89(6) . 3_545 no H2 O2 2.87(6) . 3_545 no H2 C1 2.95(6) . 3_545 no H2 C2 2.95(6) . 3_545 no H2 O2 2.81(5) . 4_555 no H3 C4 2.90(7) . 2_554 no H3 O1 2.68(7) . 4_554 no #===END _database_code_depnum_ccdc_archive 'CCDC 959696'