#------------------------------------------------------------------------------ #$Date: 2014-12-24 13:20:39 +0200 (Wed, 24 Dec 2014) $ #$Revision: 129045 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/61/7116103.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_7116103 loop_ _publ_author_name 'Lucas Henry' 'Christoph Schneider' 'Benedict Mutzel' 'Peter V. Simpson' 'Christoph Nagel' 'Katharina Fucke' 'Ulrich Schatzschneider' _publ_section_title ; Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a MnI(bpy)(CO)3-coordinated azide ; _journal_name_full Chem.Commun. _journal_page_first 15692 _journal_paper_doi 10.1039/C4cc07892F _journal_volume 50 _journal_year 2014 _chemical_formula_moiety 'C21 H17 F3 Mn N5 O5' _chemical_formula_sum 'C21 H17 F3 Mn N5 O5' _chemical_formula_weight 531.33 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_primary iterative _audit_creation_date 2013-07-19 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 16.0897(7) _cell_length_b 14.5131(6) _cell_length_c 19.1832(8) _cell_measurement_reflns_used 9885 _cell_measurement_temperature 100 _cell_measurement_theta_max 25.93 _cell_measurement_theta_min 2.47 _cell_volume 4479.5(3) _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _diffrn_ambient_temperature 100.0 _diffrn_detector 'Bruker APEX2 area detector' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.9986 _diffrn_measured_fraction_theta_max 0.9986 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART APEX2 area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_reflns_av_R_equivalents 0.0606 _diffrn_reflns_av_unetI/netI 0.0285 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 59029 _diffrn_reflns_theta_full 27.1223 _diffrn_reflns_theta_max 27.12 _diffrn_reflns_theta_min 2.17 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.658 _exptl_absorpt_correction_T_max 0.9709 _exptl_absorpt_correction_T_min 0.7974 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0609 before and 0.0564 after correction. The Ratio of minimum to maximum transmission is 0.8213. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear light yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.5756 _exptl_crystal_description prism _exptl_crystal_F_000 2164.0703 _exptl_crystal_preparation 'soaked in perfluoro polyether oil' _exptl_crystal_recrystallization_method 'by evaporation from DCM/Hexane' _exptl_crystal_size_max 0.494 _exptl_crystal_size_mid 0.152 _exptl_crystal_size_min 0.112 _refine_diff_density_max 0.4078 _refine_diff_density_min -0.4170 _refine_diff_density_rms 0.0958 _refine_ls_d_res_high 0.7795 _refine_ls_d_res_low 9.3956 _refine_ls_goodness_of_fit_ref 1.0427 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 27 _refine_ls_number_parameters 318 _refine_ls_number_reflns 4957 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.0427 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0306 _refine_ls_shift/su_max 0.0000 _refine_ls_shift/su_mean 0.0000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0316P)^2^+3.0137P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.0783 _reflns_Friedel_coverage 0.0 _reflns_limit_h_max 20 _reflns_limit_h_min 0 _reflns_limit_k_max 18 _reflns_limit_k_min 0 _reflns_limit_l_max 24 _reflns_limit_l_min 0 _reflns_number_gt 3800 _reflns_number_total 4957 _reflns_threshold_expression I>=2u(I) _[local]_cod_data_source_file c4cc07892f2.cif _[local]_cod_data_source_block '[Mn(triazolateCOOEt,CF3)(bpyCH3,CH3)(CO)3]' _cod_depositor_comments ; The following automatic conversions were performed: '_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according to the built-in table from CIF Core dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius ; _cod_database_code 7116103 _olex2_refinement_description ; ; loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 x+1/2,-y+1/2,-z 3 -x,y+1/2,-z+1/2 4 -x+1/2,-y,z+1/2 5 -x,-y,-z 6 -x-1/2,y-1/2,z 7 x,-y-1/2,z-1/2 8 x-1/2,y,-z-1/2 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_refinement_flags_posn H8a H 0.19826(13) 0.57344(16) -0.05748(10) 0.0297(6) Uiso 1.000000 R H8b H 0.15710(13) 0.67350(16) -0.04724(10) 0.0297(6) Uiso 1.000000 R H9a H 0.09404(13) 0.5086(5) 0.0144(7) 0.0364(7) Uiso 1.000000 GR H9b H 0.0528(4) 0.6082(5) 0.0237(6) 0.0364(7) Uiso 1.000000 GR H9c H 0.0524(4) 0.5591(9) -0.05100(13) 0.0364(7) Uiso 1.000000 GR H11 H 0.62235(11) 0.71838(12) 0.35651(9) 0.0169(4) Uiso 1.000000 R H13 H 0.47573(12) 0.94368(12) 0.36937(10) 0.0187(5) Uiso 1.000000 R H14 H 0.36229(12) 0.85184(12) 0.34364(9) 0.0160(4) Uiso 1.000000 R H16 H 0.62491(11) 0.57112(12) 0.33733(9) 0.0168(4) Uiso 1.000000 R H18 H 0.48503(12) 0.34379(12) 0.30377(9) 0.0175(4) Uiso 1.000000 R H19 H 0.36832(12) 0.43682(12) 0.30108(9) 0.0164(4) Uiso 1.000000 R H20a H 0.6843(2) 0.85856(16) 0.3936(7) 0.0368(7) Uiso 1.000000 GR H20b H 0.6484(6) 0.9416(7) 0.3477(3) 0.0368(7) Uiso 1.000000 GR H20c H 0.6243(3) 0.9336(8) 0.4284(4) 0.0368(7) Uiso 1.000000 GR H21a H 0.69433(12) 0.4270(2) 0.3242(7) 0.0298(6) Uiso 1.000000 GR H21b H 0.6465(4) 0.3620(7) 0.3783(3) 0.0298(6) Uiso 1.000000 GR H21c H 0.6440(4) 0.3391(6) 0.2967(5) 0.0298(6) Uiso 1.000000 GR C1 C 0.30750(11) 0.63916(13) 0.41229(10) 0.0160(4) Uani 1.000000 . C2 C 0.24593(12) 0.55851(13) 0.30827(9) 0.0153(4) Uani 1.000000 . C3 C 0.24591(12) 0.73090(13) 0.30933(9) 0.0157(4) Uani 1.000000 . C4 C 0.33262(11) 0.64706(12) 0.10375(9) 0.0133(4) Uani 1.000000 . C5 C 0.41685(11) 0.65802(12) 0.11897(9) 0.0144(4) Uani 1.000000 . C6 C 0.49049(12) 0.66622(14) 0.07235(10) 0.0206(4) Uani 1.000000 . C7 C 0.29215(12) 0.63862(13) 0.03520(9) 0.0163(4) Uani 1.000000 . C8 C 0.16606(13) 0.61271(16) -0.02506(10) 0.0248(5) Uani 1.000000 . C9 C 0.08420(13) 0.56827(16) -0.00801(10) 0.0243(5) Uani 1.000000 . C10 C 0.49909(11) 0.69497(12) 0.33964(9) 0.0119(4) Uani 1.000000 . C11 C 0.56929(11) 0.74698(12) 0.35465(9) 0.0141(4) Uani 1.000000 . C12 C 0.56174(12) 0.84097(12) 0.36693(9) 0.0155(4) Uani 1.000000 . C13 C 0.48321(12) 0.87947(12) 0.36204(10) 0.0156(4) Uani 1.000000 . C14 C 0.41572(12) 0.82425(12) 0.34646(9) 0.0133(4) Uani 1.000000 . C15 C 0.50030(11) 0.59417(12) 0.32955(9) 0.0111(4) Uani 1.000000 . C16 C 0.57260(11) 0.54189(12) 0.33113(9) 0.0140(4) Uani 1.000000 . C17 C 0.56826(11) 0.44676(13) 0.32363(9) 0.0144(4) Uani 1.000000 . C18 C 0.49037(12) 0.40823(12) 0.31124(9) 0.0145(4) Uani 1.000000 . C19 C 0.42092(12) 0.46419(12) 0.30988(9) 0.0136(4) Uani 1.000000 . C20 C 0.63617(12) 0.89872(14) 0.38581(12) 0.0245(5) Uani 1.000000 . C21 C 0.64494(12) 0.38867(13) 0.33136(10) 0.0199(4) Uani 1.000000 . N1 N 0.29126(9) 0.64241(10) 0.16472(7) 0.0126(3) Uani 1.000000 . N2 N 0.34936(9) 0.65058(10) 0.21425(8) 0.0120(3) Uani 1.000000 . N3 N 0.42623(9) 0.66007(10) 0.18826(8) 0.0140(3) Uani 1.000000 . N4 N 0.42249(9) 0.73326(10) 0.33513(7) 0.0112(3) Uani 1.000000 . N5 N 0.42455(9) 0.55589(10) 0.32049(7) 0.0113(3) Uani 1.000000 . O1 O 0.29295(10) 0.63550(10) 0.47068(7) 0.0290(3) Uani 1.000000 . O2 O 0.19326(9) 0.50541(10) 0.30494(7) 0.0256(3) Uani 1.000000 . O3 O 0.19360(9) 0.78371(10) 0.30182(8) 0.0260(3) Uani 1.000000 . O4 O 0.32878(9) 0.64381(12) -0.01925(7) 0.0330(4) Uani 1.000000 . O5 O 0.21041(8) 0.62338(10) 0.04062(7) 0.0204(3) Uani 1.000000 . F1 F 0.56035(8) 0.67933(11) 0.10863(7) 0.0402(4) Uani 1.000000 . F2 F 0.48438(8) 0.73734(9) 0.02823(6) 0.0338(3) Uani 1.000000 . F3 F 0.50235(8) 0.59127(9) 0.03320(6) 0.0297(3) Uani 1.000000 . Mn1 Mn 0.325953(16) 0.644485(18) 0.318915(13) 0.01031(8) Uani 1.000000 . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0153(9) 0.0141(9) 0.0186(10) -0.0003(7) -0.0004(7) -0.0004(7) C2 0.0160(9) 0.0153(10) 0.0147(9) 0.0039(8) -0.0004(7) 0.0017(7) C3 0.0147(9) 0.0161(10) 0.0163(9) -0.0047(8) 0.0025(8) -0.0008(7) C4 0.0161(9) 0.0100(8) 0.0136(9) -0.0000(7) 0.0020(7) -0.0000(7) C5 0.0168(9) 0.0118(9) 0.0147(9) -0.0012(7) 0.0026(7) -0.0007(7) C6 0.0180(10) 0.0259(11) 0.0179(10) -0.0038(8) 0.0030(8) -0.0014(8) C7 0.0186(10) 0.0159(10) 0.0143(9) 0.0001(8) 0.0009(7) 0.0014(7) C8 0.0248(11) 0.0378(13) 0.0116(9) -0.0013(9) -0.0046(8) -0.0002(8) C9 0.0212(11) 0.0370(13) 0.0146(10) -0.0012(9) -0.0053(8) -0.0028(9) C10 0.0133(9) 0.0124(9) 0.0102(8) 0.0010(7) 0.0004(7) 0.0005(6) C11 0.0124(9) 0.0139(9) 0.0160(9) 0.0005(7) 0.0011(7) 0.0011(7) C12 0.0181(10) 0.0150(10) 0.0134(9) -0.0043(7) 0.0020(7) 0.0001(7) C13 0.0204(10) 0.0092(9) 0.0171(9) -0.0010(7) 0.0022(8) -0.0006(7) C14 0.0170(9) 0.0122(9) 0.0108(8) 0.0020(7) 0.0014(7) 0.0006(7) C15 0.0128(9) 0.0111(9) 0.0093(9) -0.0007(7) -0.0006(7) 0.0002(6) C16 0.0130(9) 0.0161(9) 0.0129(9) 0.0003(7) -0.0003(7) -0.0006(7) C17 0.0170(9) 0.0152(9) 0.0110(8) 0.0033(7) 0.0003(7) 0.0002(7) C18 0.0203(10) 0.0096(9) 0.0137(9) 0.0004(7) -0.0001(8) -0.0007(7) C19 0.0168(9) 0.0136(9) 0.0105(9) -0.0014(7) -0.0013(7) -0.0003(7) C20 0.0185(11) 0.0180(11) 0.0371(13) -0.0053(8) 0.0002(9) -0.0030(9) C21 0.0194(10) 0.0156(10) 0.0246(11) 0.0057(8) -0.0024(8) -0.0003(8) N1 0.0140(8) 0.0116(7) 0.0122(7) 0.0001(6) -0.0012(6) 0.0001(6) N2 0.0111(7) 0.0113(7) 0.0135(7) 0.0002(6) -0.0002(6) 0.0002(6) N3 0.0134(8) 0.0144(8) 0.0141(8) -0.0007(6) 0.0019(6) -0.0010(6) N4 0.0135(8) 0.0109(7) 0.0094(7) 0.0007(6) 0.0002(6) 0.0003(5) N5 0.0137(8) 0.0107(7) 0.0095(7) 0.0004(6) -0.0002(6) 0.0006(6) O1 0.0382(9) 0.0334(9) 0.0154(7) 0.0006(7) 0.0051(6) 0.0008(6) O2 0.0212(8) 0.0224(8) 0.0332(8) -0.0101(6) -0.0027(6) 0.0029(6) O3 0.0181(8) 0.0202(8) 0.0396(9) 0.0078(6) 0.0011(6) 0.0015(6) O4 0.0256(8) 0.0600(11) 0.0134(7) -0.0087(8) 0.0015(6) 0.0011(7) O5 0.0171(7) 0.0325(8) 0.0115(6) -0.0008(6) -0.0023(5) -0.0010(5) F1 0.0163(6) 0.0785(11) 0.0258(7) -0.0135(6) 0.0039(5) -0.0078(7) F2 0.0396(8) 0.0306(7) 0.0311(7) -0.0079(6) 0.0157(6) 0.0095(5) F3 0.0313(7) 0.0298(7) 0.0280(7) 0.0025(5) 0.0138(6) -0.0083(5) Mn1 0.00963(13) 0.01026(13) 0.01104(13) 0.00019(11) 0.00074(10) 0.00035(10) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source _atom_type_scat_dispersion_source C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' F 0.01794 0.01033 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' Mn 0.34779 0.73263 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 C1 Mn1 177.60(17) O2 C2 Mn1 176.23(16) O3 C3 Mn1 177.65(17) C5 C4 C7 128.74(16) C5 C4 N1 107.69(15) C7 C4 N1 123.54(16) C4 C5 N3 108.66(16) C6 C5 C4 131.01(17) C6 C5 N3 120.33(16) C5 C6 F1 111.59(16) C5 C6 F2 112.52(16) C5 C6 F3 112.73(16) F1 C6 F2 106.35(16) F1 C6 F3 106.78(16) F2 C6 F3 106.44(16) C4 C7 O4 123.65(18) C4 C7 O5 112.28(15) O5 C7 O4 124.06(18) C9 C8 O5 106.67(15) C11 C10 C15 123.74(16) C11 C10 N4 122.02(16) C15 C10 N4 114.21(16) C12 C11 C10 119.85(17) C11 C12 C13 117.67(17) C20 C12 C11 121.17(17) C20 C12 C13 121.15(16) C14 C13 C12 119.83(17) C13 C14 N4 122.79(17) C10 C15 N5 114.38(15) C16 C15 C10 123.33(16) C16 C15 N5 122.27(16) C17 C16 C15 119.88(17) C18 C17 C16 117.50(16) C21 C17 C16 120.42(17) C21 C17 C18 122.05(17) C19 C18 C17 119.67(17) C18 C19 N5 122.86(17) C4 N1 N2 105.47(14) N1 N2 Mn1 124.37(11) N3 N2 N1 112.93(14) N3 N2 Mn1 122.66(11) C5 N3 N2 105.25(14) C10 N4 Mn1 116.29(12) C14 N4 C10 117.83(16) C14 N4 Mn1 125.70(13) C15 N5 Mn1 116.36(11) C19 N5 C15 117.69(15) C19 N5 Mn1 125.87(12) C8 O5 C7 115.60(15) C1 Mn1 N2 178.79(7) C1 Mn1 N4 90.06(7) C1 Mn1 N5 94.91(7) C2 Mn1 C1 88.02(8) C2 Mn1 C3 87.70(8) C2 Mn1 N2 92.88(7) C2 Mn1 N4 175.07(7) C2 Mn1 N5 96.93(7) C3 Mn1 C1 90.77(8) C3 Mn1 N2 90.08(7) C3 Mn1 N4 96.87(7) C3 Mn1 N5 172.79(7) N4 Mn1 N2 88.98(6) N5 Mn1 N2 84.18(6) N5 Mn1 N4 78.70(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C4 C5 1.395(3) C4 C7 1.473(2) C5 C6 1.489(3) C8 C9 1.503(3) C10 C11 1.389(2) C10 C15 1.476(2) C12 C11 1.390(3) C12 C20 1.506(3) C13 C12 1.385(3) C13 C14 1.382(3) C16 C15 1.389(2) C16 C17 1.390(3) C17 C21 1.502(2) C18 C17 1.393(3) C18 C19 1.382(3) N1 C4 1.347(2) N2 N1 1.338(2) N2 N3 1.340(2) N3 C5 1.338(2) N4 C10 1.355(2) N4 C14 1.343(2) N5 C15 1.351(2) N5 C19 1.348(2) O1 C1 1.146(2) O2 C2 1.147(2) O3 C3 1.147(2) O4 C7 1.202(2) O5 C7 1.338(2) O5 C8 1.456(2) F1 C6 1.336(2) F2 C6 1.338(2) F3 C6 1.336(2) Mn1 C1 1.8173(19) Mn1 C2 1.8046(19) Mn1 C3 1.807(2) Mn1 N2 2.0448(15) Mn1 N4 2.0418(15) Mn1 N5 2.0422(15)