#------------------------------------------------------------------------------ #$Date: 2020-02-04 22:10:12 +0200 (Tue, 04 Feb 2020) $ #$Revision: 247620 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125639.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_7125639 loop_ _publ_author_name 'Ajarul, Sk' 'Kayet, Anirban' 'Pati, Tanmay K.' 'Maiti, Dilip K.' _publ_section_title ; A competitive and highly selective 7-, 6- and 5-annulation with 1,3-migration through C-H and N-H - alkyne coupling. ; _journal_issue 3 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 474 _journal_page_last 477 _journal_paper_doi 10.1039/c9cc07360d _journal_volume 56 _journal_year 2020 _chemical_formula_moiety 'C24 H19 N O3' _chemical_formula_sum 'C24 H19 N O3' _chemical_formula_weight 369.41 _space_group_crystal_system Triclinic' _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _audit_update_record ; 2019-04-19 deposited with the CCDC. 2019-11-28 downloaded from the CCDC. ; _cell_angle_alpha 80.88(4) _cell_angle_beta 85.50(3) _cell_angle_gamma 69.03(3) _cell_formula_units_Z 2 _cell_length_a 8.893(9) _cell_length_b 10.210(11) _cell_length_c 11.258(10) _cell_measurement_reflns_used 5090 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 24.09 _cell_measurement_theta_min 2.45 _cell_volume 942.2(16) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _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 298(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type CCD _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 0.1795 _diffrn_reflns_av_sigmaI/netI 0.1363 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 30258 _diffrn_reflns_theta_full 28.42 _diffrn_reflns_theta_max 28.42 _diffrn_reflns_theta_min 2.16 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_description crystalline _exptl_crystal_F_000 438 _refine_diff_density_max 0.252 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.069 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.907 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 258 _refine_ls_number_reflns 4725 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.907 _refine_ls_R_factor_all 0.1584 _refine_ls_R_factor_gt 0.0729 _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^)+(0.1000P)^2^+0.2081P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1759 _refine_ls_wR_factor_ref 0.2191 _reflns_number_gt 2257 _reflns_number_total 4725 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c9cc07360d2.cif _cod_data_source_block ajarul_0m_a _cod_depositor_comments 'Adding full bibliography for 7125638--7125639.cif.' _cod_original_sg_symbol_H-M P-1 _cod_database_code 7125639 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; 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 O2 O 0.0507(2) 0.81542(19) 0.01530(18) 0.0524(5) Uani 1 1 d . O1 O 0.2080(2) 0.4688(2) 0.1280(2) 0.0591(6) Uani 1 1 d . O3 O 0.7936(2) 0.1316(2) 0.43598(18) 0.0589(6) Uani 1 1 d . N1 N 0.2101(3) 0.9281(2) 0.0587(2) 0.0420(6) Uani 1 1 d . C18 C 0.5261(3) 0.4973(2) 0.2169(2) 0.0324(6) Uani 1 1 d . C8 C 0.2743(3) 0.6726(3) 0.1289(2) 0.0351(6) Uani 1 1 d . C10 C 0.4356(3) 0.6287(2) 0.1396(2) 0.0334(6) Uani 1 1 d . C3 C 0.0517(3) 0.6180(3) 0.2656(2) 0.0387(6) Uani 1 1 d . C13 C 0.3309(3) 0.9518(3) 0.1170(2) 0.0379(6) Uani 1 1 d . C11 C 0.5270(3) 0.7180(3) 0.0737(2) 0.0427(7) Uani 1 1 d . H6 H 0.6418 0.6656 0.0793 0.051 Uiso 1 1 calc R H7 H 0.4998 0.7400 -0.0107 0.051 Uiso 1 1 calc R C21 C 0.6992(3) 0.2526(3) 0.3678(2) 0.0391(6) Uani 1 1 d . C7 C 0.1790(3) 0.5775(3) 0.1709(2) 0.0397(6) Uani 1 1 d . C9 C 0.1749(3) 0.8095(3) 0.0626(2) 0.0395(6) Uani 1 1 d . C12 C 0.4864(3) 0.8525(3) 0.1264(2) 0.0391(6) Uani 1 1 d . C22 C 0.7580(3) 0.2827(3) 0.2536(2) 0.0420(7) Uani 1 1 d . H14 H 0.8549 0.2209 0.2264 0.050 Uiso 1 1 calc R C19 C 0.4707(3) 0.4639(3) 0.3320(2) 0.0393(6) Uani 1 1 d . H12 H 0.3730 0.5245 0.3593 0.047 Uiso 1 1 calc R C23 C 0.6737(3) 0.4039(3) 0.1799(2) 0.0388(6) Uani 1 1 d . H15 H 0.7158 0.4241 0.1038 0.047 Uiso 1 1 calc R C20 C 0.5555(3) 0.3439(3) 0.4076(2) 0.0409(6) Uani 1 1 d . H13 H 0.5158 0.3248 0.4848 0.049 Uiso 1 1 calc R C14 C 0.2939(3) 1.0813(3) 0.1576(2) 0.0472(7) Uani 1 1 d . H8 H 0.1910 1.1488 0.1478 0.057 Uiso 1 1 calc R C17 C 0.6000(3) 0.8844(3) 0.1830(3) 0.0495(7) Uani 1 1 d . H11 H 0.7038 0.8183 0.1922 0.059 Uiso 1 1 calc R C4 C 0.0353(3) 0.7291(3) 0.3267(3) 0.0530(8) Uani 1 1 d . H3 H 0.1000 0.7836 0.3051 0.064 Uiso 1 1 calc R C2 C -0.0467(3) 0.5401(3) 0.2976(3) 0.0513(8) Uani 1 1 d . H2 H -0.0373 0.4652 0.2566 0.062 Uiso 1 1 calc R C15 C 0.4096(4) 1.1100(3) 0.2123(2) 0.0544(8) Uani 1 1 d . H9 H 0.3847 1.1964 0.2404 0.065 Uiso 1 1 calc R C16 C 0.5622(4) 1.0106(3) 0.2253(3) 0.0573(8) Uani 1 1 d . H10 H 0.6399 1.0295 0.2632 0.069 Uiso 1 1 calc R C5 C -0.0762(4) 0.7600(4) 0.4197(3) 0.0675(9) Uani 1 1 d . H4 H -0.0862 0.8347 0.4610 0.081 Uiso 1 1 calc R C1 C -0.1598(4) 0.5723(4) 0.3903(3) 0.0658(9) Uani 1 1 d . H1 H -0.2270 0.5199 0.4107 0.079 Uiso 1 1 calc R C6 C -0.1726(4) 0.6802(4) 0.4512(3) 0.0686(10) Uani 1 1 d . H5 H -0.2469 0.7004 0.5147 0.082 Uiso 1 1 calc R C24 C 0.7286(5) 0.0898(4) 0.5488(3) 0.0769(11) Uani 1 1 d . H17 H 0.6998 0.1653 0.5969 0.115 Uiso 1 1 calc R H16 H 0.8074 0.0070 0.5896 0.115 Uiso 1 1 calc R H18 H 0.6345 0.0690 0.5360 0.115 Uiso 1 1 calc R H1A H 0.124(4) 1.011(3) 0.028(3) 0.064(9) Uiso 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 O2 0.0428(10) 0.0462(12) 0.0664(13) -0.0055(10) -0.0236(10) -0.0098(9) O1 0.0590(13) 0.0480(13) 0.0771(15) -0.0259(11) 0.0026(11) -0.0208(11) O3 0.0639(13) 0.0431(12) 0.0555(13) 0.0049(10) -0.0135(11) -0.0038(10) N1 0.0391(12) 0.0330(13) 0.0503(14) 0.0003(10) -0.0143(11) -0.0080(11) C18 0.0302(12) 0.0328(14) 0.0355(14) -0.0072(11) -0.0047(11) -0.0108(11) C8 0.0357(13) 0.0328(14) 0.0360(14) -0.0063(11) -0.0038(11) -0.0098(11) C10 0.0358(13) 0.0304(13) 0.0335(13) -0.0080(11) -0.0020(11) -0.0092(11) C3 0.0307(12) 0.0392(15) 0.0460(15) -0.0038(12) -0.0080(12) -0.0113(12) C13 0.0408(14) 0.0369(15) 0.0355(14) 0.0028(11) -0.0065(11) -0.0152(12) C11 0.0371(14) 0.0423(16) 0.0445(15) -0.0038(13) 0.0007(12) -0.0103(12) C21 0.0402(14) 0.0326(14) 0.0433(15) -0.0046(12) -0.0123(12) -0.0094(12) C7 0.0353(13) 0.0362(15) 0.0463(15) -0.0071(12) -0.0118(12) -0.0081(12) C9 0.0349(13) 0.0403(16) 0.0395(14) -0.0036(12) -0.0075(12) -0.0082(12) C12 0.0411(14) 0.0394(15) 0.0372(14) 0.0029(12) -0.0034(11) -0.0175(12) C22 0.0375(14) 0.0373(15) 0.0472(16) -0.0128(12) -0.0036(12) -0.0048(12) C19 0.0304(13) 0.0433(16) 0.0428(15) -0.0087(12) -0.0025(11) -0.0097(12) C23 0.0378(14) 0.0407(15) 0.0382(14) -0.0086(12) 0.0001(12) -0.0130(12) C20 0.0431(15) 0.0461(16) 0.0344(14) -0.0022(12) -0.0029(12) -0.0176(13) C14 0.0530(16) 0.0395(16) 0.0462(16) -0.0029(13) -0.0055(13) -0.0130(14) C17 0.0462(16) 0.0486(18) 0.0548(17) 0.0061(14) -0.0133(14) -0.0210(14) C4 0.0463(16) 0.0542(19) 0.0627(19) -0.0168(15) 0.0040(15) -0.0201(15) C2 0.0425(15) 0.0524(18) 0.0616(19) -0.0010(15) -0.0087(15) -0.0214(14) C15 0.080(2) 0.0423(17) 0.0469(17) -0.0078(14) -0.0070(16) -0.0272(17) C16 0.069(2) 0.055(2) 0.0564(19) 0.0030(15) -0.0240(16) -0.0315(18) C5 0.0565(19) 0.078(2) 0.070(2) -0.0322(19) 0.0104(17) -0.0201(18) C1 0.0438(17) 0.083(3) 0.073(2) 0.004(2) -0.0020(17) -0.0311(18) C6 0.0414(17) 0.095(3) 0.063(2) -0.010(2) 0.0076(16) -0.0182(19) C24 0.109(3) 0.062(2) 0.0435(19) 0.0059(16) -0.0081(19) -0.014(2) 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' Cl Cl 0.1484 0.1585 '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 C21 O3 C24 117.3(2) C9 N1 C13 130.3(2) C9 N1 H1A 112.1(17) C13 N1 H1A 115.6(18) C19 C18 C23 117.0(2) C19 C18 C10 121.1(2) C23 C18 C10 121.9(2) C10 C8 C9 124.8(2) C10 C8 C7 122.5(2) C9 C8 C7 112.2(2) C8 C10 C18 122.2(2) C8 C10 C11 119.5(2) C18 C10 C11 118.3(2) C2 C3 C4 118.9(3) C2 C3 C7 120.1(3) C4 C3 C7 121.0(2) C14 C13 C12 120.5(2) C14 C13 N1 118.2(2) C12 C13 N1 121.2(2) C12 C11 C10 110.4(2) C12 C11 H6 109.6 C10 C11 H6 109.6 C12 C11 H7 109.6 C10 C11 H7 109.6 H6 C11 H7 108.1 O3 C21 C20 124.1(3) O3 C21 C22 116.0(2) C20 C21 C22 119.8(2) O1 C7 C3 121.2(2) O1 C7 C8 119.8(2) C3 C7 C8 119.0(2) O2 C9 N1 119.9(2) O2 C9 C8 118.1(2) N1 C9 C8 122.0(2) C17 C12 C13 118.0(3) C17 C12 C11 122.4(3) C13 C12 C11 119.6(2) C23 C22 C21 120.2(2) C23 C22 H14 119.9 C21 C22 H14 119.9 C20 C19 C18 122.3(2) C20 C19 H12 118.9 C18 C19 H12 118.9 C22 C23 C18 121.3(2) C22 C23 H15 119.3 C18 C23 H15 119.3 C21 C20 C19 119.4(2) C21 C20 H13 120.3 C19 C20 H13 120.3 C15 C14 C13 120.0(3) C15 C14 H8 120.0 C13 C14 H8 120.0 C16 C17 C12 121.3(3) C16 C17 H11 119.3 C12 C17 H11 119.3 C3 C4 C5 120.5(3) C3 C4 H3 119.8 C5 C4 H3 119.8 C3 C2 C1 120.5(3) C3 C2 H2 119.7 C1 C2 H2 119.7 C16 C15 C14 119.8(3) C16 C15 H9 120.1 C14 C15 H9 120.1 C17 C16 C15 120.3(3) C17 C16 H10 119.8 C15 C16 H10 119.8 C6 C5 C4 119.9(3) C6 C5 H4 120.0 C4 C5 H4 120.0 C6 C1 C2 119.9(3) C6 C1 H1 120.0 C2 C1 H1 120.0 C1 C6 C5 120.3(3) C1 C6 H5 119.9 C5 C6 H5 119.9 O3 C24 H17 109.5 O3 C24 H16 109.5 H17 C24 H16 109.5 O3 C24 H18 109.5 H17 C24 H18 109.5 H16 C24 H18 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O2 C9 1.241(3) O1 C7 1.215(3) O3 C21 1.370(3) O3 C24 1.421(4) N1 C9 1.348(4) N1 C13 1.412(3) N1 H1A 0.96(3) C18 C19 1.385(4) C18 C23 1.397(4) C18 C10 1.474(3) C8 C10 1.350(4) C8 C9 1.477(4) C8 C7 1.506(4) C10 C11 1.505(3) C3 C2 1.374(4) C3 C4 1.376(4) C3 C7 1.484(4) C13 C14 1.386(4) C13 C12 1.392(4) C11 C12 1.496(4) C11 H6 0.9700 C11 H7 0.9700 C21 C20 1.376(4) C21 C22 1.381(4) C12 C17 1.391(4) C22 C23 1.375(4) C22 H14 0.9300 C19 C20 1.380(4) C19 H12 0.9300 C23 H15 0.9300 C20 H13 0.9300 C14 C15 1.377(4) C14 H8 0.9300 C17 C16 1.364(4) C17 H11 0.9300 C4 C5 1.377(4) C4 H3 0.9300 C2 C1 1.384(4) C2 H2 0.9300 C15 C16 1.375(4) C15 H9 0.9300 C16 H10 0.9300 C5 C6 1.372(5) C5 H4 0.9300 C1 C6 1.355(5) C1 H1 0.9300 C6 H5 0.9300 C24 H17 0.9600 C24 H16 0.9600 C24 H18 0.9600