#------------------------------------------------------------------------------ #$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/75/1517513.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1517513 loop_ _publ_author_name 'Markovits, Iulius I. E.' 'Anthofer, Michael H.' 'Kolding, Helene' 'Cokoja, Mirza' 'P\"othig, Alexander' 'Raba, Andreas' 'Herrmann, Wolfgang A.' 'Fehrmann, Rasmus' 'K\"uhn, Fritz E.' _publ_section_title ; Efficient epoxidation of propene using molecular catalysts ; _journal_issue 11 _journal_name_full 'Catal. Sci. Technol.' _journal_page_first 3845 _journal_paper_doi 10.1039/C4CY01066C _journal_volume 4 _journal_year 2014 _chemical_compound_source 'see text' _chemical_formula_moiety 'C13 H11 N4, F6 P' _chemical_formula_sum 'C13 H11 F6 N4 P' _chemical_formula_weight 368.23 _chemical_name_systematic ? _space_group_IT_number 11 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 11 _symmetry_space_group_name_Hall '-P 2yb' _symmetry_space_group_name_H-M 'P 1 21/m 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 102.836(1) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 6.2172(2) _cell_length_b 16.4455(5) _cell_length_c 7.0797(2) _cell_measurement_reflns_used 9916 _cell_measurement_temperature 123 _cell_measurement_theta_max 25.3348 _cell_measurement_theta_min 2.9510 _cell_volume 705.77(4) _computing_cell_refinement 'SAINT (Bruker, 2008b)' _computing_data_collection 'APEX II Control Software (Bruker, 2008a)' _computing_data_reduction 'SAINT (Bruker, 2008b)' _computing_molecular_graphics 'PLATON (Spek, 2011)' _computing_publication_material 'PLATON (Spek, 2011), enCIFer (Allen, 2004)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997), SHELXLE (Huebschle, 2011)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 123 _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 16 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Bruker APEX-II CCD ' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_radiation_monochromator 'MONTEL optic' _diffrn_radiation_probe x-ray _diffrn_radiation_source 'rotating anode FR591' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 21380 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 25.37 _diffrn_reflns_theta_max 25.37 _diffrn_reflns_theta_min 2.95 _exptl_absorpt_coefficient_mu 0.270 _exptl_absorpt_correction_T_max 0.921 _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 2008b' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.733 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description fragment _exptl_crystal_F_000 372 _exptl_crystal_size_max 0.520 _exptl_crystal_size_mid 0.470 _exptl_crystal_size_min 0.310 _refine_diff_density_max 0.218 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.042 _refine_ls_extinction_coef 0.063(9) _refine_ls_extinction_expression FC^*^=KFC[1+0.001XFC^2^\L^3^/SIN(2\Q)]^-1/4^ _refine_ls_extinction_method shelxl _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 116 _refine_ls_number_reflns 1334 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.101 _refine_ls_R_factor_all 0.0282 _refine_ls_R_factor_gt 0.0279 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0270P)^2^+0.3497P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0681 _refine_ls_wR_factor_ref 0.0683 _reflns_number_gt 1315 _reflns_number_total 1334 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; ; _cod_data_source_file c4cy01066c2.cif _cod_data_source_block compound_a _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius Adding full bibliography for 1517513.cif. ; _cod_original_sg_symbol_H-M 'P 21/m' _cod_database_code 1517513 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,-z 3 -x,-y,-z 4 x,1/2-y,z 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 N1 0.0183(5) 0.0155(5) 0.0152(5) 0.0002(4) 0.0040(4) 0.0000(4) N2 0.0217(6) 0.0174(6) 0.0200(5) -0.0006(4) 0.0039(4) 0.0018(4) C1 0.0195(9) 0.0163(9) 0.0173(8) 0.0000 0.0057(7) 0.0000 C2 0.0174(6) 0.0205(6) 0.0173(6) -0.0004(5) 0.0057(5) 0.0009(5) C3 0.0220(6) 0.0150(6) 0.0133(6) -0.0008(4) 0.0028(5) -0.0008(5) C4 0.0205(6) 0.0218(7) 0.0211(6) -0.0014(5) 0.0051(5) 0.0007(5) C5 0.0244(7) 0.0267(7) 0.0233(7) -0.0019(5) 0.0059(5) -0.0079(5) C6 0.0336(7) 0.0170(6) 0.0189(6) -0.0011(5) 0.0020(5) -0.0051(5) C7 0.0281(7) 0.0166(6) 0.0218(7) -0.0016(5) 0.0023(5) 0.0029(5) P1 0.0153(3) 0.0190(3) 0.0168(3) 0.0000 0.0045(2) 0.0000 F1 0.0428(5) 0.0276(5) 0.0329(5) 0.0104(4) 0.0075(4) 0.0066(4) F2 0.0562(6) 0.0468(6) 0.0335(5) -0.0184(4) 0.0077(4) 0.0120(5) F3 0.0180(6) 0.0784(11) 0.0571(9) 0.0000 0.0122(6) 0.0000 F4 0.0181(6) 0.0252(6) 0.0522(8) 0.0000 0.0052(5) 0.0000 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 N1 N Uani -0.02784(16) 0.31569(6) 0.80463(14) 1.000 0.0163(3) d . N2 N Uani -0.13674(17) 0.45091(6) 0.77574(15) 1.000 0.0198(3) d . C1 C Uani 0.0674(3) 0.25000 0.7489(2) 1.000 0.0175(5) d S C2 C Uani -0.1906(2) 0.29082(8) 0.89788(17) 1.000 0.0181(3) d . C3 C Uani 0.0269(2) 0.39933(7) 0.77642(17) 1.000 0.0169(3) d . C4 C Uani 0.2362(2) 0.41949(8) 0.75601(18) 1.000 0.0211(4) d . C5 C Uani 0.2755(2) 0.50111(8) 0.72651(19) 1.000 0.0247(4) d . C6 C Uani 0.1085(2) 0.55703(8) 0.72264(18) 1.000 0.0238(4) d . C7 C Uani -0.0923(2) 0.52957(8) 0.74959(18) 1.000 0.0227(4) d . P1 P Uani 0.45202(7) 0.25000 0.31259(6) 1.000 0.0169(2) d S F1 F Uani 0.43565(15) 0.31880(5) 0.15038(12) 1.000 0.0346(3) d . F2 F Uani 0.46830(17) 0.31887(6) 0.47437(13) 1.000 0.0459(3) d . F3 F Uani 0.1903(2) 0.25000 0.2813(2) 1.000 0.0506(5) d S F4 F Uani 0.71345(18) 0.25000 0.34460(19) 1.000 0.0322(4) d S H1 H Uiso 0.18320 0.25000 0.68110 1.000 0.0210 c SR H2 H Uiso -0.28450 0.32510 0.95170 1.000 0.0220 c R H4 H Uiso 0.34780 0.37950 0.76190 1.000 0.0250 c R H5 H Uiso 0.41570 0.51840 0.70920 1.000 0.0300 c R H6 H Uiso 0.13150 0.61310 0.70190 1.000 0.0290 c R H7 H Uiso -0.20530 0.56840 0.74970 1.000 0.0270 c R 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' F F 0.0171 0.0103 ' 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' P P 0.1023 0.0942 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 F2 P1 F4 89.88(5) . . yes F1 P1 F2 179.90(5) 4_555 . yes F2 P1 F2 90.27(5) . 4_555 yes F3 P1 F4 179.81(8) . . yes F1 P1 F3 90.00(5) 4_555 . yes F2 P1 F3 89.99(6) 4_555 . yes F1 P1 F4 90.13(5) 4_555 . yes F2 P1 F4 89.88(5) 4_555 . yes F1 P1 F2 89.83(5) 4_555 4_555 yes F1 P1 F4 90.13(5) . . yes F1 P1 F2 89.83(4) . . yes F1 P1 F3 90.00(5) . . yes F2 P1 F3 89.99(6) . . yes F1 P1 F1 90.07(5) . 4_555 yes F1 P1 F2 179.90(5) . 4_555 yes C1 N1 C2 108.72(11) . . yes C1 N1 C3 126.74(11) . . yes C2 N1 C3 124.54(10) . . yes C3 N2 C7 115.84(11) . . yes N1 C1 N1 108.27(14) . 4_555 yes N1 C2 C2 107.15(11) . 4_555 yes N2 C3 C4 125.94(11) . . yes N1 C3 N2 114.02(11) . . yes N1 C3 C4 120.03(11) . . yes C3 C4 C5 116.69(12) . . no C4 C5 C6 119.31(12) . . no C5 C6 C7 118.55(12) . . no N2 C7 C6 123.63(12) . . yes N1 C1 H1 126.00 . . no N1 C1 H1 126.00 4_555 . no N1 C2 H2 126.00 . . no C2 C2 H2 126.00 4_555 . no C3 C4 H4 122.00 . . no C5 C4 H4 122.00 . . no C4 C5 H5 120.00 . . no C6 C5 H5 120.00 . . no C5 C6 H6 121.00 . . no C7 C6 H6 121.00 . . no N2 C7 H7 118.00 . . no C6 C7 H7 118.00 . . no 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 F3 1.5927(14) . yes P1 F1 1.5992(9) . yes P1 F2 1.5979(10) . yes P1 F2 1.5979(10) 4_555 yes P1 F4 1.5904(12) . yes P1 F1 1.5992(9) 4_555 yes N1 C1 1.3331(14) . yes N1 C3 1.4415(15) . yes N1 C2 1.3871(16) . yes N2 C3 1.3238(16) . yes N2 C7 1.3442(16) . yes C2 C2 1.3426(19) 4_555 no C3 C4 1.3812(18) . no C4 C5 1.3884(19) . no C5 C6 1.3827(18) . no C6 C7 1.3801(18) . no C1 H1 0.9500 . no C2 H2 0.9500 . no C4 H4 0.9500 . no C5 H5 0.9500 . no C6 H6 0.9500 . no C7 H7 0.9500 . no 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 _geom_hbond_publ_flag C2 H2 F1 0.9500 2.4700 3.2638(15) 141.00 1_456 yes C4 H4 F2 0.9500 2.5300 3.1741(16) 126.00 . yes C6 H6 F4 0.9500 2.5000 3.4289(14) 166.00 2_656 yes C7 H7 F1 0.9500 2.5400 3.4566(16) 163.00 3_566 yes 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_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 N1 -0.45(15) . 4_555 no C3 N1 C1 N1 179.01(11) . 4_555 no C1 N1 C2 C2 0.28(14) . 4_555 no C3 N1 C2 C2 -179.20(11) . 4_555 no C1 N1 C3 N2 155.53(13) . . no C1 N1 C3 C4 -25.43(18) . . no C2 N1 C3 N2 -25.08(16) . . no C2 N1 C3 C4 153.96(12) . . no C7 N2 C3 N1 -179.93(11) . . no C7 N2 C3 C4 1.10(18) . . no C3 N2 C7 C6 0.67(18) . . no N1 C2 C2 N1 0.02(15) 4_555 4_555 no N1 C3 C4 C5 179.08(11) . . no N2 C3 C4 C5 -2.00(19) . . no C3 C4 C5 C6 1.15(18) . . no C4 C5 C6 C7 0.38(19) . . no C5 C6 C7 N2 -1.38(19) . . no