#------------------------------------------------------------------------------ #$Date: 2019-11-24 15:42:41 +0200 (Sun, 24 Nov 2019) $ #$Revision: 238396 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/52/1555216.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_1555216 loop_ _publ_author_name 'Jia, Feng-Cheng' 'Zhou, Zhi-Wen' 'Xu, Cheng' 'Cai, Qun' 'Li, Deng-Kui' 'Wu, An-Xin' _publ_section_title ; Expeditious Synthesis of 2-Phenylquinazolin-4-amines via a Fe/Cu Relay-Catalyzed Domino Strategy. ; _journal_issue 17 _journal_name_full 'Organic letters' _journal_page_first 4236 _journal_page_last 4239 _journal_paper_doi 10.1021/acs.orglett.5b02020 _journal_volume 17 _journal_year 2015 _chemical_formula_sum 'C14 H11 N3' _chemical_formula_weight 221.26 _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/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 106.898(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 14.857(4) _cell_length_b 12.127(3) _cell_length_c 13.289(4) _cell_measurement_reflns_used 8222 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 32.00 _cell_measurement_theta_min 2.21 _cell_volume 2290.9(11) _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, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w 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 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 9807 _diffrn_reflns_theta_full 28.00 _diffrn_reflns_theta_max 28.00 _diffrn_reflns_theta_min 2.21 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_correction_T_min 0.9843 _exptl_absorpt_correction_type none _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 928 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.240 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.072 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 160 _refine_ls_number_reflns 2761 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0421 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0674P)^2^+1.3927P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1175 _refine_ls_wR_factor_ref 0.1202 _reflns_number_gt 2560 _reflns_number_total 2761 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ol5b02020_si_001.cif _cod_data_source_block g:\150113l\work\mo_150113l_0m _cod_depositor_comments ; The following automatic conversions were performed: data item '_symmetry_cell_setting' value 'Monoclinic' was changed to 'monoclinic' in accordance with the /home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas ; _cod_original_cell_volume 2291.0(10) _cod_original_sg_symbol_H-M C2/c _cod_database_code 1555216 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 C1 C 0.21867(6) 1.02919(8) 0.21653(7) 0.0159(2) Uani 1 1 d . C2 C 0.27962(7) 1.10228(8) 0.28706(8) 0.0196(2) Uani 1 1 d . H2 H 0.2686 1.1201 0.3521 0.024 Uiso 1 1 calc R C3 C 0.35513(7) 1.14781(9) 0.26169(9) 0.0226(2) Uani 1 1 d . H3 H 0.3963 1.1967 0.3094 0.027 Uiso 1 1 calc R C4 C 0.37129(7) 1.12209(9) 0.16521(9) 0.0235(2) Uani 1 1 d . H4 H 0.4229 1.1548 0.1477 0.028 Uiso 1 1 calc R C5 C 0.31335(7) 1.05015(9) 0.09594(8) 0.0209(2) Uani 1 1 d . H5 H 0.3253 1.0332 0.0312 0.025 Uiso 1 1 calc R C6 C 0.23600(6) 1.00138(8) 0.12061(7) 0.0161(2) Uani 1 1 d . C7 C 0.10367(6) 0.89417(8) 0.07323(7) 0.0148(2) Uani 1 1 d . C8 C 0.13505(7) 0.98193(8) 0.23364(7) 0.0164(2) Uani 1 1 d . C9 C 0.04107(7) 0.81517(8) -0.00052(7) 0.0161(2) Uani 1 1 d . C10 C 0.07919(7) 0.73801(9) -0.05462(8) 0.0229(2) Uani 1 1 d . H10 H 0.1448 0.7383 -0.0471 0.027 Uiso 1 1 calc R C11 C 0.02128(8) 0.66086(10) -0.11932(9) 0.0296(3) Uani 1 1 d . H11 H 0.0477 0.6075 -0.1548 0.036 Uiso 1 1 calc R C12 C -0.07507(8) 0.66093(9) -0.13270(9) 0.0278(3) Uani 1 1 d . H12 H -0.1143 0.6081 -0.1774 0.033 Uiso 1 1 calc R C13 C -0.11369(7) 0.73848(9) -0.08054(8) 0.0229(2) Uani 1 1 d . H13 H -0.1797 0.7398 -0.0906 0.028 Uiso 1 1 calc R C14 C -0.05583(7) 0.81419(8) -0.01358(8) 0.0190(2) Uani 1 1 d . H14 H -0.0823 0.8657 0.0237 0.023 Uiso 1 1 calc R N1 N 0.17901(6) 0.92963(7) 0.04909(6) 0.01646(19) Uani 1 1 d . N2 N 0.07708(6) 0.91926(7) 0.16021(6) 0.01644(19) Uani 1 1 d . N3 N 0.11198(6) 0.99878(8) 0.32231(7) 0.0225(2) Uani 1 1 d D H3B H 0.1464(9) 1.0377(11) 0.3748(9) 0.027 Uiso 1 1 d D H3A H 0.0608(8) 0.9682(11) 0.3297(11) 0.027 Uiso 1 1 d 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 C1 0.0168(4) 0.0159(4) 0.0141(4) 0.0009(3) 0.0033(3) 0.0012(3) C2 0.0213(5) 0.0191(5) 0.0172(5) -0.0023(4) 0.0037(4) 0.0006(4) C3 0.0203(5) 0.0202(5) 0.0245(5) -0.0032(4) 0.0021(4) -0.0024(4) C4 0.0193(5) 0.0245(5) 0.0270(5) 0.0015(4) 0.0072(4) -0.0031(4) C5 0.0197(5) 0.0251(5) 0.0186(5) 0.0011(4) 0.0070(4) -0.0002(4) C6 0.0173(4) 0.0160(4) 0.0143(4) 0.0017(3) 0.0036(3) 0.0016(3) C7 0.0176(4) 0.0147(4) 0.0117(4) 0.0018(3) 0.0034(3) 0.0018(3) C8 0.0192(4) 0.0166(4) 0.0131(4) 0.0008(3) 0.0043(3) 0.0013(3) C9 0.0199(5) 0.0159(4) 0.0114(4) 0.0017(3) 0.0028(3) -0.0002(3) C10 0.0219(5) 0.0251(5) 0.0196(5) -0.0044(4) 0.0029(4) 0.0030(4) C11 0.0317(6) 0.0264(5) 0.0268(6) -0.0109(4) 0.0023(4) 0.0054(4) C12 0.0309(6) 0.0218(5) 0.0250(5) -0.0062(4) -0.0008(4) -0.0036(4) C13 0.0212(5) 0.0234(5) 0.0218(5) 0.0006(4) 0.0024(4) -0.0037(4) C14 0.0207(5) 0.0190(5) 0.0168(5) 0.0004(3) 0.0045(4) -0.0002(3) N1 0.0176(4) 0.0186(4) 0.0131(4) 0.0003(3) 0.0042(3) 0.0007(3) N2 0.0188(4) 0.0182(4) 0.0126(4) 0.0002(3) 0.0050(3) -0.0010(3) N3 0.0238(4) 0.0308(5) 0.0141(4) -0.0052(3) 0.0075(3) -0.0067(3) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C1 C6 119.95(9) C2 C1 C8 124.04(9) C6 C1 C8 115.97(8) C3 C2 C1 120.03(9) C3 C2 H2 120.0 C1 C2 H2 120.0 C2 C3 C4 120.08(9) C2 C3 H3 120.0 C4 C3 H3 120.0 C5 C4 C3 120.78(9) C5 C4 H4 119.6 C3 C4 H4 119.6 C4 C5 C6 120.23(9) C4 C5 H5 119.9 C6 C5 H5 119.9 N1 C6 C1 122.34(9) N1 C6 C5 118.75(9) C1 C6 C5 118.90(9) N1 C7 N2 127.49(9) N1 C7 C9 117.43(8) N2 C7 C9 115.05(8) N3 C8 N2 117.10(9) N3 C8 C1 122.09(9) N2 C8 C1 120.81(9) C10 C9 C14 119.15(9) C10 C9 C7 120.08(9) C14 C9 C7 120.72(8) C11 C10 C9 119.98(10) C11 C10 H10 120.0 C9 C10 H10 120.0 C10 C11 C12 120.59(10) C10 C11 H11 119.7 C12 C11 H11 119.7 C13 C12 C11 119.76(10) C13 C12 H12 120.1 C11 C12 H12 120.1 C12 C13 C14 119.96(10) C12 C13 H13 120.0 C14 C13 H13 120.0 C13 C14 C9 120.53(9) C13 C14 H14 119.7 C9 C14 H14 119.7 C7 N1 C6 115.50(8) C8 N2 C7 117.61(8) C8 N3 H3B 123.1(9) C8 N3 H3A 119.2(10) H3B N3 H3A 117.7(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.4110(13) C1 C6 1.4126(13) C1 C8 1.4449(13) C2 C3 1.3772(15) C2 H2 0.9500 C3 C4 1.4064(16) C3 H3 0.9500 C4 C5 1.3743(15) C4 H4 0.9500 C5 C6 1.4132(14) C5 H5 0.9500 C6 N1 1.3819(12) C7 N1 1.3227(13) C7 N2 1.3602(12) C7 C9 1.4878(13) C8 N3 1.3352(13) C8 N2 1.3353(13) C9 C10 1.3964(14) C9 C14 1.3992(14) C10 C11 1.3874(15) C10 H10 0.9500 C11 C12 1.3902(17) C11 H11 0.9500 C12 C13 1.3876(16) C12 H12 0.9500 C13 C14 1.3889(14) C13 H13 0.9500 C14 H14 0.9500 N3 H3B 0.874(9) N3 H3A 0.877(9) 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 N3 H3B N1 0.874(9) 2.259(11) 3.0139(14) 144.6(12) 6_576 N3 H3A N2 0.877(9) 2.174(9) 3.0420(14) 170.4(14) 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 C6 C1 C2 C3 1.01(15) C8 C1 C2 C3 -176.62(9) C1 C2 C3 C4 0.39(16) C2 C3 C4 C5 -1.10(16) C3 C4 C5 C6 0.40(16) C2 C1 C6 N1 179.51(8) C8 C1 C6 N1 -2.68(13) C2 C1 C6 C5 -1.68(14) C8 C1 C6 C5 176.13(9) C4 C5 C6 N1 179.84(9) C4 C5 C6 C1 0.99(15) C2 C1 C8 N3 -4.39(15) C6 C1 C8 N3 177.90(9) C2 C1 C8 N2 175.38(9) C6 C1 C8 N2 -2.33(14) N1 C7 C9 C10 34.05(13) N2 C7 C9 C10 -144.30(9) N1 C7 C9 C14 -148.43(9) N2 C7 C9 C14 33.22(12) C14 C9 C10 C11 -0.77(15) C7 C9 C10 C11 176.79(10) C9 C10 C11 C12 1.36(18) C10 C11 C12 C13 -0.30(18) C11 C12 C13 C14 -1.33(17) C12 C13 C14 C9 1.91(15) C10 C9 C14 C13 -0.86(14) C7 C9 C14 C13 -178.40(9) N2 C7 N1 C6 -0.82(14) C9 C7 N1 C6 -178.94(8) C1 C6 N1 C7 4.17(13) C5 C6 N1 C7 -174.64(9) N3 C8 N2 C7 -174.80(9) C1 C8 N2 C7 5.41(14) N1 C7 N2 C8 -4.01(15) C9 C7 N2 C8 174.15(8)