#------------------------------------------------------------------------------ #$Date: 2012-03-01 15:39:10 +0200 (Thu, 01 Mar 2012) $ #$Revision: 37125 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/32/1503245.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_1503245 loop_ _publ_author_name 'Chen, Zhiyuan' 'Wu, Jie' _publ_section_title ; Efficient generation of biologically active H-pyrazolo[5,1-a]isoquinolines via multicomponent reaction. ; _journal_issue 21 _journal_name_full 'Organic letters' _journal_page_first 4856 _journal_page_last 4859 _journal_volume 12 _journal_year 2010 _chemical_formula_sum 'C22 H20 N2 O' _chemical_formula_weight 328.40 _chemical_name_systematic ; ? ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _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 100.141(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 21.376(5) _cell_length_b 9.2038(18) _cell_length_c 17.855(4) _cell_measurement_reflns_used 1756 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 22.43 _cell_measurement_theta_min 2.32 _cell_volume 3457.9(13) _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 296(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 0.0881 _diffrn_reflns_av_sigmaI/netI 0.0905 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 8901 _diffrn_reflns_theta_full 26.01 _diffrn_reflns_theta_max 26.01 _diffrn_reflns_theta_min 1.94 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6681 _exptl_absorpt_correction_type multi-scan _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.33 _refine_diff_density_max 0.231 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.055 _refine_ls_extinction_coef 0.0015(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.921 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 228 _refine_ls_number_reflns 3413 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.921 _refine_ls_R_factor_all 0.1062 _refine_ls_R_factor_gt 0.0570 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0781P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1374 _refine_ls_wR_factor_ref 0.1596 _reflns_number_gt 1823 _reflns_number_total 3413 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file ol101988q_si_002.cif _[local]_cod_data_source_block 100122wu_0ma _[local]_cod_cif_authors_sg_H-M C2/c _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 3457.9(12) _cod_database_code 1503245 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 N1 N 0.06930(8) 0.7153(2) 0.12281(10) 0.0446(5) Uani 1 1 d . C7 C 0.11058(9) 0.6331(2) 0.08989(12) 0.0410(6) Uani 1 1 d . O1 O 0.25781(7) 0.5406(2) 0.09582(9) 0.0582(5) Uani 1 1 d . N2 N 0.09110(9) 0.7444(2) 0.19797(10) 0.0551(6) Uani 1 1 d . C6 C 0.09378(9) 0.5994(3) 0.01011(11) 0.0403(6) Uani 1 1 d . C11 C 0.00947(10) 0.7642(3) 0.08565(13) 0.0491(6) Uani 1 1 d . C5 C 0.03473(10) 0.6513(3) -0.02900(12) 0.0465(6) Uani 1 1 d . C4 C 0.01759(12) 0.6193(3) -0.10736(12) 0.0591(7) Uani 1 1 d . H4 H -0.0215 0.6504 -0.1339 0.071 Uiso 1 1 calc R C16 C 0.21953(10) 0.5077(3) 0.15122(13) 0.0504(6) Uani 1 1 d . H16 H 0.2461 0.5207 0.2014 0.061 Uiso 1 1 calc R C10 C -0.00578(11) 0.7303(3) 0.01188(13) 0.0534(7) Uani 1 1 d . H10 H -0.0452 0.7601 -0.0144 0.064 Uiso 1 1 calc R C17 C 0.20195(10) 0.3484(3) 0.14338(12) 0.0471(6) Uani 1 1 d . C1 C 0.13315(11) 0.5219(3) -0.02978(12) 0.0504(6) Uani 1 1 d . H1 H 0.1722 0.4882 -0.0043 0.061 Uiso 1 1 calc R C3 C 0.05754(12) 0.5436(3) -0.14435(13) 0.0630(8) Uani 1 1 d . H3 H 0.0458 0.5248 -0.1961 0.076 Uiso 1 1 calc R C12 C -0.02934(11) 0.8414(3) 0.13297(15) 0.0630(7) Uani 1 1 d . H12 H -0.0300 0.7957 0.1824 0.076 Uiso 1 1 calc R C22 C 0.15950(11) 0.2897(3) 0.18557(14) 0.0626(8) Uani 1 1 d . H22 H 0.1419 0.3494 0.2184 0.075 Uiso 1 1 calc R C2 C 0.11532(12) 0.4945(3) -0.10591(13) 0.0603(7) Uani 1 1 d . H2 H 0.1422 0.4427 -0.1318 0.072 Uiso 1 1 calc R C9 C 0.14694(11) 0.6768(3) 0.21078(12) 0.0534(7) Uani 1 1 d . H9 H 0.1736 0.6777 0.2580 0.064 Uiso 1 1 calc R C8 C 0.16245(10) 0.6045(3) 0.14801(12) 0.0445(6) Uani 1 1 d . C18 C 0.22831(11) 0.2553(3) 0.09687(14) 0.0589(7) Uani 1 1 d . H18 H 0.2580 0.2905 0.0691 0.071 Uiso 1 1 calc R C20 C 0.16830(13) 0.0540(3) 0.13211(17) 0.0718(8) Uani 1 1 d . H20 H 0.1568 -0.0435 0.1278 0.086 Uiso 1 1 calc R C21 C 0.14283(13) 0.1447(4) 0.17980(17) 0.0717(8) Uani 1 1 d . H21 H 0.1141 0.1081 0.2085 0.086 Uiso 1 1 calc R C19 C 0.21108(13) 0.1101(3) 0.09096(16) 0.0708(8) Uani 1 1 d . H19 H 0.2288 0.0497 0.0585 0.085 Uiso 1 1 calc R C15 C 0.28535(13) 0.6809(3) 0.10293(17) 0.0784(9) Uani 1 1 d . H15A H 0.2526 0.7528 0.0910 0.118 Uiso 1 1 calc R H15B H 0.3149 0.6901 0.0685 0.118 Uiso 1 1 calc R H15C H 0.3072 0.6949 0.1542 0.118 Uiso 1 1 calc R C13 C -0.08819(15) 0.9144(5) 0.1003(2) 0.1104(14) Uani 1 1 d . H13A H -0.1234 0.9090 0.1279 0.133 Uiso 1 1 calc R H13B H -0.1003 0.9149 0.0454 0.133 Uiso 1 1 calc R C14 C -0.03284(18) 0.9992(4) 0.1338(2) 0.1029(12) Uani 1 1 d . H14A H -0.0336 1.0465 0.1821 0.123 Uiso 1 1 calc R H14B H -0.0106 1.0524 0.0996 0.123 Uiso 1 1 calc R 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 N1 0.0382(10) 0.0529(13) 0.0445(10) 0.0024(10) 0.0123(8) 0.0028(9) C7 0.0335(11) 0.0473(15) 0.0449(12) 0.0014(11) 0.0142(10) 0.0007(10) O1 0.0390(9) 0.0682(13) 0.0699(11) 0.0003(10) 0.0168(8) -0.0047(9) N2 0.0543(13) 0.0699(16) 0.0443(11) -0.0006(10) 0.0177(9) 0.0036(11) C6 0.0338(11) 0.0453(14) 0.0429(12) 0.0038(11) 0.0096(10) 0.0010(10) C11 0.0377(13) 0.0514(16) 0.0618(15) 0.0084(13) 0.0186(12) 0.0074(11) C5 0.0378(12) 0.0527(16) 0.0488(13) 0.0068(12) 0.0070(10) -0.0004(12) C4 0.0504(15) 0.072(2) 0.0510(14) 0.0054(14) -0.0033(12) 0.0019(14) C16 0.0361(12) 0.0696(19) 0.0453(13) 0.0073(13) 0.0063(10) -0.0017(12) C10 0.0361(13) 0.0602(18) 0.0629(16) 0.0077(13) 0.0062(12) 0.0060(12) C17 0.0311(11) 0.0612(18) 0.0470(13) 0.0104(12) 0.0013(10) 0.0046(11) C1 0.0392(12) 0.0635(17) 0.0488(14) -0.0020(12) 0.0081(11) 0.0036(12) C3 0.0650(17) 0.079(2) 0.0433(14) -0.0020(13) 0.0036(13) -0.0032(15) C12 0.0534(15) 0.0667(19) 0.0744(17) 0.0088(15) 0.0262(14) 0.0159(14) C22 0.0495(15) 0.074(2) 0.0664(16) 0.0100(15) 0.0168(13) 0.0063(14) C2 0.0555(15) 0.079(2) 0.0483(14) -0.0083(14) 0.0158(13) 0.0029(15) C9 0.0491(14) 0.0679(19) 0.0429(13) 0.0016(13) 0.0076(11) 0.0027(13) C8 0.0387(12) 0.0530(16) 0.0427(12) 0.0016(11) 0.0097(10) 0.0013(11) C18 0.0467(14) 0.064(2) 0.0683(16) 0.0083(15) 0.0177(13) 0.0002(13) C20 0.0646(18) 0.059(2) 0.089(2) 0.0119(17) 0.0075(16) -0.0040(15) C21 0.0562(16) 0.076(2) 0.0865(19) 0.0238(18) 0.0228(15) -0.0063(16) C19 0.0656(17) 0.064(2) 0.0854(19) 0.0025(17) 0.0217(16) 0.0051(16) C15 0.0647(18) 0.074(2) 0.098(2) 0.0054(18) 0.0195(17) -0.0169(17) C13 0.0605(19) 0.143(4) 0.124(3) -0.035(3) 0.006(2) 0.052(2) C14 0.115(3) 0.070(2) 0.142(3) -0.005(2) 0.071(3) 0.009(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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N2 N1 C7 113.27(18) N2 N1 C11 121.64(19) C7 N1 C11 125.08(19) N1 C7 C8 105.73(18) N1 C7 C6 118.41(19) C8 C7 C6 135.9(2) C15 O1 C16 114.4(2) C9 N2 N1 102.57(18) C1 C6 C5 119.2(2) C1 C6 C7 123.3(2) C5 C6 C7 117.5(2) C10 C11 N1 115.7(2) C10 C11 C12 128.0(2) N1 C11 C12 116.3(2) C4 C5 C6 118.1(2) C4 C5 C10 122.5(2) C6 C5 C10 119.3(2) C3 C4 C5 120.8(2) C3 C4 H4 119.6 C5 C4 H4 119.6 O1 C16 C8 114.17(19) O1 C16 C17 107.80(19) C8 C16 C17 112.56(18) O1 C16 H16 107.3 C8 C16 H16 107.3 C17 C16 H16 107.3 C11 C10 C5 123.9(2) C11 C10 H10 118.0 C5 C10 H10 118.0 C18 C17 C22 117.4(3) C18 C17 C16 122.4(2) C22 C17 C16 120.2(2) C2 C1 C6 121.0(2) C2 C1 H1 119.5 C6 C1 H1 119.5 C4 C3 C2 120.7(2) C4 C3 H3 119.7 C2 C3 H3 119.7 C13 C12 C14 60.0(2) C13 C12 C11 122.0(3) C14 C12 C11 121.6(2) C13 C12 H12 114.2 C14 C12 H12 114.2 C11 C12 H12 114.2 C21 C22 C17 121.4(3) C21 C22 H22 119.3 C17 C22 H22 119.3 C1 C2 C3 120.1(2) C1 C2 H2 119.9 C3 C2 H2 119.9 N2 C9 C8 114.8(2) N2 C9 H9 122.6 C8 C9 H9 122.6 C9 C8 C7 103.66(19) C9 C8 C16 124.0(2) C7 C8 C16 132.0(2) C17 C18 C19 120.9(2) C17 C18 H18 119.6 C19 C18 H18 119.6 C21 C20 C19 118.6(3) C21 C20 H20 120.7 C19 C20 H20 120.7 C20 C21 C22 120.6(3) C20 C21 H21 119.7 C22 C21 H21 119.7 C20 C19 C18 121.1(3) C20 C19 H19 119.5 C18 C19 H19 119.5 O1 C15 H15A 109.5 O1 C15 H15B 109.5 H15A C15 H15B 109.5 O1 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C12 C13 C14 60.0(2) C12 C13 H13A 117.8 C14 C13 H13A 117.8 C12 C13 H13B 117.8 C14 C13 H13B 117.8 H13A C13 H13B 114.9 C13 C14 C12 60.0(2) C13 C14 H14A 117.8 C12 C14 H14A 117.8 C13 C14 H14B 117.8 C12 C14 H14B 117.8 H14A C14 H14B 114.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 N2 1.367(2) N1 C7 1.371(3) N1 C11 1.407(3) C7 C8 1.404(3) C7 C6 1.440(3) O1 C15 1.415(3) O1 C16 1.423(2) N2 C9 1.330(3) C6 C1 1.391(3) C6 C5 1.414(3) C11 C10 1.337(3) C11 C12 1.468(3) C5 C4 1.414(3) C5 C10 1.426(3) C4 C3 1.360(3) C4 H4 0.9300 C16 C8 1.504(3) C16 C17 1.514(4) C16 H16 0.9800 C10 H10 0.9300 C17 C18 1.381(3) C17 C22 1.387(3) C1 C2 1.369(3) C1 H1 0.9300 C3 C2 1.379(3) C3 H3 0.9300 C12 C13 1.455(4) C12 C14 1.455(4) C12 H12 0.9800 C22 C21 1.381(4) C22 H22 0.9300 C2 H2 0.9300 C9 C8 1.393(3) C9 H9 0.9300 C18 C19 1.385(4) C18 H18 0.9300 C20 C21 1.372(4) C20 C19 1.371(4) C20 H20 0.9300 C21 H21 0.9300 C19 H19 0.9300 C15 H15A 0.9600 C15 H15B 0.9600 C15 H15C 0.9600 C13 C14 1.455(5) C13 H13A 0.9700 C13 H13B 0.9700 C14 H14A 0.9700 C14 H14B 0.9700 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 N2 N1 C7 C8 1.1(3) C11 N1 C7 C8 -177.5(2) N2 N1 C7 C6 -177.98(19) C11 N1 C7 C6 3.4(3) C7 N1 N2 C9 -0.5(3) C11 N1 N2 C9 178.2(2) N1 C7 C6 C1 177.3(2) C8 C7 C6 C1 -1.4(4) N1 C7 C6 C5 -1.2(3) C8 C7 C6 C5 -179.9(3) N2 N1 C11 C10 179.0(2) C7 N1 C11 C10 -2.5(3) N2 N1 C11 C12 -3.0(3) C7 N1 C11 C12 175.4(2) C1 C6 C5 C4 1.3(3) C7 C6 C5 C4 179.9(2) C1 C6 C5 C10 179.8(2) C7 C6 C5 C10 -1.6(3) C6 C5 C4 C3 -1.5(4) C10 C5 C4 C3 -180.0(2) C15 O1 C16 C8 62.5(3) C15 O1 C16 C17 -171.68(19) N1 C11 C10 C5 -0.6(4) C12 C11 C10 C5 -178.3(2) C4 C5 C10 C11 -178.9(2) C6 C5 C10 C11 2.6(4) O1 C16 C17 C18 8.4(3) C8 C16 C17 C18 135.2(2) O1 C16 C17 C22 -173.71(18) C8 C16 C17 C22 -46.9(3) C5 C6 C1 C2 -0.5(4) C7 C6 C1 C2 -179.0(2) C5 C4 C3 C2 1.0(4) C10 C11 C12 C13 -10.7(5) N1 C11 C12 C13 171.7(3) C10 C11 C12 C14 -82.8(4) N1 C11 C12 C14 99.6(3) C18 C17 C22 C21 -1.7(3) C16 C17 C22 C21 -179.7(2) C6 C1 C2 C3 -0.1(4) C4 C3 C2 C1 -0.1(4) N1 N2 C9 C8 -0.4(3) N2 C9 C8 C7 1.0(3) N2 C9 C8 C16 -173.1(2) N1 C7 C8 C9 -1.2(2) C6 C7 C8 C9 177.6(3) N1 C7 C8 C16 172.2(2) C6 C7 C8 C16 -9.0(5) O1 C16 C8 C9 -129.0(2) C17 C16 C8 C9 107.7(3) O1 C16 C8 C7 58.7(3) C17 C16 C8 C7 -64.6(3) C22 C17 C18 C19 2.2(4) C16 C17 C18 C19 -179.9(2) C19 C20 C21 C22 0.7(4) C17 C22 C21 C20 0.4(4) C21 C20 C19 C18 -0.2(4) C17 C18 C19 C20 -1.2(4) C11 C12 C13 C14 -110.7(3) C11 C12 C14 C13 111.3(3)