#------------------------------------------------------------------------------ #$Date: 2015-03-04 20:35:54 +0200 (Wed, 04 Mar 2015) $ #$Revision: 133006 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/86/1518656.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_1518656 loop_ _publ_author_name 'Pawar, Amit B.' 'Chang, Sukbok' _publ_section_title ; Cobalt-Catalyzed C-H Cyanation of (Hetero)arenes and 6-Arylpurines with N-Cyanosuccinimide as a New Cyanating Agent. ; _journal_issue 3 _journal_name_full 'Organic letters' _journal_page_first 660 _journal_page_last 663 _journal_paper_doi 10.1021/ol503680d _journal_volume 17 _journal_year 2015 _chemical_formula_moiety 'C13 H10 N4 O' _chemical_formula_sum 'C13 H10 N4 O' _chemical_formula_weight 238.25 _chemical_name_systematic ; ? ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 85.814(4) _cell_angle_beta 78.171(4) _cell_angle_gamma 89.197(4) _cell_formula_units_Z 2 _cell_length_a 6.9373(6) _cell_length_b 8.2261(7) _cell_length_c 9.7516(8) _cell_measurement_reflns_used 33282 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 28.00 _cell_measurement_theta_min 3.00 _cell_volume 543.22(8) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Photon 100 CMOS detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0101 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 33282 _diffrn_reflns_theta_full 28.00 _diffrn_reflns_theta_max 28.00 _diffrn_reflns_theta_min 3.00 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_T_max 0.9835 _exptl_absorpt_correction_T_min 0.9462 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour White _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description Platy _exptl_crystal_F_000 248 _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.334 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.065 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 2612 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.093 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0359 _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^)+(0.0604P)^2^+0.1467P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1014 _refine_ls_wR_factor_ref 0.1033 _reflns_number_gt 2446 _reflns_number_total 2612 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file ol503680d_si_003.cif _[local]_cod_data_source_block n0176b-1 _[local]_cod_cif_authors_sg_H-M P-1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas Adding full bibliography for 1518655--1518657.cif. ; _cod_database_code 1518656 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 O1 O -0.18932(13) 0.17850(11) 0.88551(8) 0.0310(2) Uani 1 1 d . N1 N 0.04188(12) 0.27265(10) 0.41153(8) 0.01680(18) Uani 1 1 d . N2 N 0.29857(13) 0.17500(11) 0.24420(9) 0.0217(2) Uani 1 1 d . N3 N 0.11047(13) 0.40795(11) 0.18993(9) 0.0235(2) Uani 1 1 d . N4 N -0.37223(15) 0.45958(13) 0.29107(10) 0.0294(2) Uani 1 1 d . C1 C 0.12497(15) 0.05639(13) 0.79979(10) 0.0225(2) Uani 1 1 d . H1A H 0.0995 -0.0584 0.7846 0.027 Uiso 1 1 calc R H1B H 0.1482 0.0597 0.8964 0.027 Uiso 1 1 calc R C2 C -0.05482(15) 0.15815(12) 0.78591(10) 0.0205(2) Uani 1 1 d . C3 C -0.05793(14) 0.22479(12) 0.64330(10) 0.0182(2) Uani 1 1 d . C4 C 0.09505(14) 0.20242(11) 0.53073(10) 0.0166(2) Uani 1 1 d . C5 C 0.28530(14) 0.12092(12) 0.54191(10) 0.0201(2) Uani 1 1 d . H5A H 0.3961 0.1817 0.4801 0.024 Uiso 1 1 calc R H5B H 0.2859 0.0086 0.5117 0.024 Uiso 1 1 calc R C6 C 0.30951(15) 0.11656(13) 0.69487(10) 0.0222(2) Uani 1 1 d . H6A H 0.4212 0.0442 0.7064 0.027 Uiso 1 1 calc R H6B H 0.3421 0.2275 0.7163 0.027 Uiso 1 1 calc R C7 C -0.20970(14) 0.31247(12) 0.59321(10) 0.0198(2) Uani 1 1 d . H7A H -0.3317 0.3453 0.6477 0.024 Uiso 1 1 calc R C8 C -0.14660(14) 0.34080(12) 0.45105(10) 0.0182(2) Uani 1 1 d . C9 C 0.15850(14) 0.28616(12) 0.27296(10) 0.0174(2) Uani 1 1 d . C10 C 0.22104(16) 0.42015(14) 0.05959(11) 0.0258(2) Uani 1 1 d . H10A H 0.1922 0.5039 -0.0056 0.031 Uiso 1 1 calc R C11 C 0.37539(16) 0.31535(14) 0.01659(10) 0.0239(2) Uani 1 1 d . H11A H 0.4547 0.3267 -0.0754 0.029 Uiso 1 1 calc R C12 C 0.40853(16) 0.19333(14) 0.11390(11) 0.0242(2) Uani 1 1 d . H12A H 0.5136 0.1193 0.0875 0.029 Uiso 1 1 calc R C13 C -0.26122(15) 0.40897(12) 0.35595(11) 0.0214(2) 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 O1 0.0285(4) 0.0404(5) 0.0185(4) 0.0020(3) 0.0060(3) 0.0070(3) N1 0.0151(4) 0.0192(4) 0.0148(4) -0.0001(3) -0.0006(3) 0.0027(3) N2 0.0225(4) 0.0242(4) 0.0164(4) -0.0011(3) 0.0001(3) 0.0051(3) N3 0.0222(4) 0.0261(4) 0.0197(4) 0.0036(3) -0.0005(3) 0.0037(3) N4 0.0253(5) 0.0349(5) 0.0271(5) 0.0026(4) -0.0059(4) 0.0071(4) C1 0.0221(5) 0.0265(5) 0.0178(4) 0.0029(4) -0.0030(4) 0.0017(4) C2 0.0204(5) 0.0226(5) 0.0165(4) -0.0001(3) -0.0001(3) -0.0005(4) C3 0.0167(4) 0.0203(4) 0.0162(4) -0.0008(3) -0.0002(3) 0.0014(3) C4 0.0168(4) 0.0174(4) 0.0150(4) -0.0005(3) -0.0018(3) 0.0009(3) C5 0.0173(4) 0.0249(5) 0.0168(4) 0.0003(3) -0.0015(3) 0.0047(4) C6 0.0186(5) 0.0292(5) 0.0181(5) 0.0011(4) -0.0035(4) 0.0028(4) C7 0.0165(4) 0.0221(5) 0.0193(5) -0.0011(3) -0.0001(3) 0.0028(3) C8 0.0149(4) 0.0191(4) 0.0194(4) -0.0005(3) -0.0010(3) 0.0025(3) C9 0.0166(4) 0.0199(4) 0.0150(4) -0.0012(3) -0.0015(3) -0.0010(3) C10 0.0249(5) 0.0317(5) 0.0184(5) 0.0056(4) -0.0020(4) 0.0019(4) C11 0.0223(5) 0.0333(6) 0.0146(4) -0.0007(4) -0.0002(4) -0.0007(4) C12 0.0230(5) 0.0299(5) 0.0180(5) -0.0037(4) 0.0005(4) 0.0049(4) C13 0.0192(5) 0.0221(5) 0.0215(5) -0.0004(4) -0.0014(4) 0.0028(4) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C4 N1 C8 107.94(8) C4 N1 C9 127.26(8) C8 N1 C9 124.67(8) C9 N2 C12 114.48(9) C9 N3 C10 114.81(9) C2 C1 C6 112.29(8) O1 C2 C3 122.66(10) O1 C2 C1 122.49(9) C3 C2 C1 114.82(8) C4 C3 C7 108.49(8) C4 C3 C2 122.59(9) C7 C3 C2 128.86(9) N1 C4 C3 107.99(8) N1 C4 C5 127.43(8) C3 C4 C5 124.55(9) C4 C5 C6 108.88(8) C1 C6 C5 113.00(8) C8 C7 C3 106.77(8) C7 C8 N1 108.82(8) C7 C8 C13 125.83(9) N1 C8 C13 124.90(9) N3 C9 N2 128.92(9) N3 C9 N1 115.10(8) N2 C9 N1 115.98(8) N3 C10 C11 122.38(10) C12 C11 C10 116.65(9) N2 C12 C11 122.72(9) N4 C13 C8 172.16(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C2 1.2206(12) N1 C4 1.3758(12) N1 C8 1.4060(12) N1 C9 1.4231(11) N2 C9 1.3266(13) N2 C12 1.3405(13) N3 C9 1.3241(13) N3 C10 1.3409(13) N4 C13 1.1485(14) C1 C2 1.5160(14) C1 C6 1.5289(14) C2 C3 1.4613(13) C3 C4 1.3825(13) C3 C7 1.4162(13) C4 C5 1.4923(13) C5 C6 1.5327(13) C7 C8 1.3691(13) C8 C13 1.4215(14) C10 C11 1.3815(15) C11 C12 1.3802(15) 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 C6 C1 C2 O1 -149.55(10) C6 C1 C2 C3 32.63(12) O1 C2 C3 C4 179.62(10) C1 C2 C3 C4 -2.56(14) O1 C2 C3 C7 -3.47(17) C1 C2 C3 C7 174.35(10) C8 N1 C4 C3 0.46(11) C9 N1 C4 C3 176.41(9) C8 N1 C4 C5 -177.45(9) C9 N1 C4 C5 -1.50(16) C7 C3 C4 N1 -0.52(11) C2 C3 C4 N1 176.94(9) C7 C3 C4 C5 177.46(9) C2 C3 C4 C5 -5.07(15) N1 C4 C5 C6 159.83(9) C3 C4 C5 C6 -17.76(13) C2 C1 C6 C5 -57.01(12) C4 C5 C6 C1 47.69(11) C4 C3 C7 C8 0.38(11) C2 C3 C7 C8 -176.88(10) C3 C7 C8 N1 -0.10(11) C3 C7 C8 C13 172.49(9) C4 N1 C8 C7 -0.22(11) C9 N1 C8 C7 -176.30(8) C4 N1 C8 C13 -172.89(9) C9 N1 C8 C13 11.03(15) C10 N3 C9 N2 -0.73(17) C10 N3 C9 N1 179.92(9) C12 N2 C9 N3 2.09(16) C12 N2 C9 N1 -178.57(8) C4 N1 C9 N3 -154.87(10) C8 N1 C9 N3 20.44(14) C4 N1 C9 N2 25.70(14) C8 N1 C9 N2 -158.99(9) C9 N3 C10 C11 -1.18(16) N3 C10 C11 C12 1.51(17) C9 N2 C12 C11 -1.59(16) C10 C11 C12 N2 -0.02(17) C7 C8 C13 N4 -17.6(9) N1 C8 C13 N4 153.8(8)