#------------------------------------------------------------------------------ #$Date: 2015-02-04 11:52:21 +0200 (Wed, 04 Feb 2015) $ #$Revision: 130878 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/86/1518655.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_1518655 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_name_full 'Organic letters' _journal_page_first 150120094418009 _journal_paper_doi 10.1021/ol503680d _journal_year 2015 _chemical_formula_moiety 'C13 H10 N2 O2 S' _chemical_formula_sum 'C13 H10 N2 O2 S' _chemical_formula_weight 258.29 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 111.533(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.9124(16) _cell_length_b 7.5041(10) _cell_length_c 14.670(2) _cell_measurement_reflns_used 35311 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 31.75 _cell_measurement_theta_min 2.87 _cell_volume 1219.9(3) _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 0.968 _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 0.0726 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 35311 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 31.75 _diffrn_reflns_theta_min 2.87 _exptl_absorpt_coefficient_mu 0.260 _exptl_absorpt_correction_T_max 0.9795 _exptl_absorpt_correction_T_min 0.9745 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description platy _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.300 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 4009 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.1170 _refine_ls_R_factor_gt 0.0543 _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^)+(0.0633P)^2^+0.3377P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1187 _refine_ls_wR_factor_ref 0.1399 _reflns_number_gt 2451 _reflns_number_total 4009 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file ol503680d_si_002.cif _[local]_cod_data_source_block n0169a-2 _[local]_cod_cif_authors_sg_H-M P2(1)/c _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/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 ; _cod_database_code 1518655 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags S1 S 0.11444(4) 0.11051(7) 0.39354(3) 0.04112(15) Uani 1 1 d . O1 O 0.15582(13) 0.1889(3) 0.32259(11) 0.0694(5) Uani 1 1 d . O2 O 0.02424(12) 0.20058(19) 0.41928(11) 0.0550(4) Uani 1 1 d . N1 N 0.52039(14) 0.1043(2) 0.85506(11) 0.0416(4) Uani 1 1 d . N2 N 0.26831(16) -0.1226(3) 0.81651(12) 0.0571(5) Uani 1 1 d . C1 C 0.61378(19) 0.1007(3) 0.94035(14) 0.0490(5) Uani 1 1 d . H1A H 0.6001 0.1355 0.9977 0.059 Uiso 1 1 calc R C2 C 0.72844(18) 0.0497(3) 0.95035(14) 0.0501(5) Uani 1 1 d . H2A H 0.7920 0.0508 1.0128 0.060 Uiso 1 1 calc R C3 C 0.74947(16) -0.0029(3) 0.86827(15) 0.0510(5) Uani 1 1 d . H3A H 0.8279 -0.0382 0.8728 0.061 Uiso 1 1 calc R C4 C 0.65414(15) -0.0033(3) 0.77898(13) 0.0427(4) Uani 1 1 d . H4A H 0.6655 -0.0411 0.7212 0.051 Uiso 1 1 calc R C5 C 0.54169(14) 0.0526(2) 0.77551(12) 0.0337(4) Uani 1 1 d . C6 C 0.43684(14) 0.0593(2) 0.68085(12) 0.0321(3) Uani 1 1 d . C7 C 0.45189(15) 0.1176(2) 0.59604(12) 0.0364(4) Uani 1 1 d . H7A H 0.5304 0.1493 0.5990 0.044 Uiso 1 1 calc R C8 C 0.35556(15) 0.1309(2) 0.50733(13) 0.0373(4) Uani 1 1 d . H8A H 0.3674 0.1731 0.4505 0.045 Uiso 1 1 calc R C9 C 0.24152(14) 0.0813(2) 0.50320(12) 0.0337(4) Uani 1 1 d . C10 C 0.22353(14) 0.0186(2) 0.58556(12) 0.0357(4) Uani 1 1 d . H10A H 0.1454 -0.0175 0.5814 0.043 Uiso 1 1 calc R C11 C 0.32057(14) 0.0088(2) 0.67443(12) 0.0324(3) Uani 1 1 d . C12 C 0.06172(19) -0.1050(3) 0.35574(17) 0.0596(6) Uani 1 1 d . H12A H -0.0094 -0.0987 0.2950 0.089 Uiso 1 1 calc R H12B H 0.0399 -0.1630 0.4068 0.089 Uiso 1 1 calc R H12C H 0.1251 -0.1740 0.3443 0.089 Uiso 1 1 calc R C13 C 0.29603(15) -0.0607(3) 0.75719(13) 0.0394(4) 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 S1 0.0305(2) 0.0522(3) 0.0347(2) 0.0018(2) 0.00507(17) 0.00549(18) O1 0.0480(8) 0.1079(14) 0.0450(8) 0.0278(9) 0.0086(7) 0.0058(9) O2 0.0370(7) 0.0572(9) 0.0636(9) -0.0058(7) 0.0100(6) 0.0124(6) N1 0.0427(8) 0.0466(9) 0.0323(7) -0.0050(7) 0.0099(6) 0.0000(7) N2 0.0546(10) 0.0787(13) 0.0407(9) 0.0018(9) 0.0207(8) -0.0136(9) C1 0.0540(11) 0.0519(11) 0.0335(9) -0.0066(8) 0.0070(8) -0.0018(9) C2 0.0452(10) 0.0511(11) 0.0379(10) 0.0019(9) -0.0038(8) -0.0057(9) C3 0.0324(8) 0.0593(13) 0.0539(12) 0.0064(10) 0.0073(8) 0.0017(9) C4 0.0363(8) 0.0521(11) 0.0384(10) 0.0010(8) 0.0120(8) 0.0011(8) C5 0.0332(8) 0.0338(8) 0.0314(8) -0.0003(7) 0.0089(7) -0.0033(6) C6 0.0303(7) 0.0340(8) 0.0303(8) -0.0030(7) 0.0093(6) -0.0013(6) C7 0.0298(7) 0.0451(9) 0.0344(9) 0.0003(7) 0.0121(7) -0.0046(7) C8 0.0353(8) 0.0459(10) 0.0311(8) 0.0014(7) 0.0125(7) -0.0010(7) C9 0.0297(7) 0.0376(9) 0.0304(8) -0.0018(7) 0.0072(6) 0.0022(6) C10 0.0287(7) 0.0417(9) 0.0367(9) -0.0016(7) 0.0119(7) -0.0016(7) C11 0.0326(7) 0.0348(8) 0.0315(8) -0.0017(7) 0.0137(7) 0.0000(7) C12 0.0445(11) 0.0646(13) 0.0571(13) -0.0238(11) 0.0039(10) 0.0020(10) C13 0.0336(8) 0.0493(10) 0.0347(9) -0.0007(8) 0.0119(7) -0.0022(7) 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' S S 0.1246 0.1234 '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 O1 S1 O2 119.31(10) O1 S1 C12 109.19(12) O2 S1 C12 107.63(10) O1 S1 C9 107.67(9) O2 S1 C9 107.01(8) C12 S1 C9 105.14(9) C1 N1 C5 116.83(16) N1 C1 C2 124.04(19) C1 C2 C3 118.69(17) C2 C3 C4 118.68(18) C3 C4 C5 118.72(18) N1 C5 C4 123.02(15) N1 C5 C6 116.12(14) C4 C5 C6 120.85(15) C7 C6 C11 118.18(14) C7 C6 C5 120.36(14) C11 C6 C5 121.46(14) C8 C7 C6 121.87(15) C7 C8 C9 118.75(16) C10 C9 C8 121.02(15) C10 C9 S1 118.68(12) C8 C9 S1 120.19(13) C9 C10 C11 119.62(15) C10 C11 C6 120.53(15) C10 C11 C13 116.83(14) C6 C11 C13 122.60(15) N2 C13 C11 174.04(19) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O1 1.4315(16) S1 O2 1.4324(14) S1 C12 1.750(2) S1 C9 1.7719(16) N1 C1 1.335(2) N1 C5 1.340(2) N2 C13 1.137(2) C1 C2 1.373(3) C2 C3 1.375(3) C3 C4 1.383(2) C4 C5 1.387(2) C5 C6 1.489(2) C6 C7 1.391(2) C6 C11 1.405(2) C7 C8 1.387(2) C8 C9 1.388(2) C9 C10 1.385(2) C10 C11 1.391(2) C11 C13 1.446(2) 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 C5 N1 C1 C2 0.8(3) N1 C1 C2 C3 -0.7(3) C1 C2 C3 C4 -0.3(3) C2 C3 C4 C5 1.2(3) C1 N1 C5 C4 0.1(3) C1 N1 C5 C6 -179.37(16) C3 C4 C5 N1 -1.1(3) C3 C4 C5 C6 178.35(17) N1 C5 C6 C7 139.95(17) C4 C5 C6 C7 -39.6(2) N1 C5 C6 C11 -39.6(2) C4 C5 C6 C11 140.92(18) C11 C6 C7 C8 1.6(3) C5 C6 C7 C8 -177.93(16) C6 C7 C8 C9 -1.2(3) C7 C8 C9 C10 -0.4(3) C7 C8 C9 S1 175.68(13) O1 S1 C9 C10 175.54(15) O2 S1 C9 C10 46.14(16) C12 S1 C9 C10 -68.13(16) O1 S1 C9 C8 -0.63(18) O2 S1 C9 C8 -130.03(15) C12 S1 C9 C8 115.70(16) C8 C9 C10 C11 1.5(3) S1 C9 C10 C11 -174.66(13) C9 C10 C11 C6 -1.0(3) C9 C10 C11 C13 -179.00(16) C7 C6 C11 C10 -0.5(2) C5 C6 C11 C10 179.04(15) C7 C6 C11 C13 177.38(16) C5 C6 C11 C13 -3.1(3) C10 C11 C13 N2 24(2) C6 C11 C13 N2 -154.4(19)