#------------------------------------------------------------------------------ #$Date: 2008-06-25 12:31:45 +0300 (Wed, 25 Jun 2008) $ #$Revision: 403 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/7101888.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_7101888 loop_ _publ_author_name 'Batchu, Venkateswara Rao' 'Barange, Deepak Kumar' 'Kumar, Dinesh' 'Sreekanth, Bukkapattanam R' 'Vyas, K' 'Reddy, E Amarender' 'Pal, Manojit' _publ_section_title ; Tandem C-C coupling--intramolecular acetylenic Schmidt reaction under Pd/C-Cu catalysis. ; _journal_issue 19 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 1966 _journal_page_last 1968 _journal_year 2007 _chemical_formula_moiety 'C14 H14 N2 O2 ' _chemical_formula_sum 'C14 H14 N2 O2 ' _chemical_formula_weight 242.28 _space_group_IT_number 29 _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 29 _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 23.78(1) _cell_length_b 4.560(3) _cell_length_c 11.134(7) _cell_measurement_reflns_used 4826 _cell_measurement_temperature 298 _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 1.8 _cell_volume 1207.3(12) _diffrn_detector_area_resol_mean 7.31 _diffrn_measured_fraction_theta_full 0.9801 _diffrn_measured_fraction_theta_max 0.9635 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 13936 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 27.46 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_correction_T_min 0.974 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_description platelet _exptl_crystal_F_000 512.00 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.33 _refine_diff_density_min -0.37 _refine_ls_extinction_coef 275.7(20) _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 178 _refine_ls_number_reflns 1231 _refine_ls_R_factor_gt 0.0560 _refine_ls_shift/su_max 0.0000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 3861.1500 5318.8000 1509.9700 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.0650 _reflns_number_gt 917 _reflns_number_total 1401 _reflns_threshold_expression F^2^>2.0\s(F^2^) _[local]_cod_data_source_file b617823e.txt _[local]_cod_data_source_block '__DKB_006' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,+Y,1/2+Z 3 1/2+X,-Y,+Z 4 -X,-Y,1/2+Z loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.35992(11) -0.0544(7) 0.3052(2) 1.000 0.0673(8) . . O2 O Uani 0.54862(9) 0.5287(6) 0.0515(2) 1.000 0.0594(10) . . N1 N Uani 0.35389(9) 0.2670(5) 0.1579(2) 1.000 0.0378(6) . . N2 N Uani 0.2861(2) 0.8568(11) -0.3099(3) 1.000 0.0877(18) . . C1 C Uani 0.38530(10) 0.1032(8) 0.2346(3) 1.000 0.0500(12) . . C2 C Uani 0.44615(13) 0.1327(8) 0.2282(3) 1.000 0.0450(12) . . C3 C Uani 0.48020(10) -0.0256(9) 0.3089(3) 1.000 0.0547(12) . . C4 C Uani 0.53760(10) 0.0013(9) 0.3000(3) 1.000 0.0557(12) . . C5 C Uani 0.5620(2) 0.1859(8) 0.2149(3) 1.000 0.0517(12) . . C6 C Uani 0.52865(13) 0.3411(7) 0.1369(3) 1.000 0.0457(12) . . C7 C Uani 0.46951(13) 0.3176(7) 0.1427(3) 1.000 0.0413(12) . . C8 C Uani 0.43364(13) 0.4782(8) 0.0638(3) 1.000 0.0440(12) . . C9 C Uani 0.37800(10) 0.4503(8) 0.0736(3) 1.000 0.0470(12) . . C10 C Uani 0.33400(10) 0.6066(7) 0.0004(3) 1.000 0.0537(12) . . C11 C Uani 0.2925(2) 0.3947(8) -0.0609(4) 1.000 0.0650(14) . . C12 C Uani 0.2465(2) 0.5532(8) -0.1292(4) 1.000 0.0680(14) . . C13 C Uani 0.2687(2) 0.7245(10) -0.2341(4) 1.000 0.0657(16) . . C14 C Uani 0.60840(10) 0.5672(10) 0.0443(4) 1.000 0.0690(16) . . H1 H Uiso 0.31410 0.25610 0.16320 1.000 0.0460 calc R H2 H Uiso 0.46360 -0.15190 0.36680 1.000 0.0650 calc R H3 H Uiso 0.56100 -0.10970 0.35220 1.000 0.0670 calc R H4 H Uiso 0.60170 0.20860 0.21280 1.000 0.0620 calc R H5 H Uiso 0.44920 0.60310 0.00420 1.000 0.0530 calc R H6 H Uiso 0.31310 0.73010 0.05280 1.000 0.0640 calc R H7 H Uiso 0.35200 0.72260 -0.05910 1.000 0.0640 calc R H8 H Uiso 0.27540 0.27390 -0.00170 1.000 0.0780 calc R H9 H Uiso 0.31310 0.27590 -0.11540 1.000 0.0780 calc R H10 H Uiso 0.22080 0.41120 -0.15890 1.000 0.0820 calc R H11 H Uiso 0.22750 0.68270 -0.07620 1.000 0.0820 calc R H12 H Uiso 0.61940 0.72630 0.09420 1.000 0.0830 calc R H13 H Uiso 0.61870 0.60740 -0.03650 1.000 0.0830 calc R H14 H Uiso 0.62730 0.39410 0.06930 1.000 0.0830 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 O1 0.0590(10) 0.086(2) 0.0570(10) 0.014(2) 0.0014(13) -0.0210(10) O2 0.0441(13) 0.079(2) 0.055(2) 0.008(2) 0.0047(12) -0.0062(13) N1 0.0240(10) 0.0500(10) 0.0394(13) 0.0029(12) -0.0019(12) -0.0049(10) N2 0.061(2) 0.131(4) 0.071(3) 0.012(3) 0.002(2) 0.005(2) C1 0.048(2) 0.060(2) 0.042(2) -0.003(2) 0.002(2) -0.008(2) C2 0.044(2) 0.049(2) 0.042(2) -0.004(2) -0.002(2) -0.0060(10) C3 0.059(2) 0.054(2) 0.051(2) 0.007(2) -0.006(2) -0.005(2) C4 0.050(2) 0.061(2) 0.056(2) 0.004(2) -0.012(2) 0.002(2) C5 0.046(2) 0.059(2) 0.050(2) -0.004(2) -0.005(2) 0.001(2) C6 0.039(2) 0.051(2) 0.047(2) -0.005(2) 0.003(2) -0.0040(10) C7 0.044(2) 0.045(2) 0.035(2) -0.003(2) 0.0000(10) -0.0004(13) C8 0.044(2) 0.050(2) 0.038(2) -0.003(2) 0.0000(10) 0.0010(10) C9 0.047(2) 0.052(2) 0.042(2) -0.005(2) 0.001(2) 0.002(2) C10 0.050(2) 0.053(2) 0.058(2) 0.000(2) -0.011(2) 0.008(2) C11 0.060(2) 0.058(2) 0.077(3) 0.000(2) -0.019(2) 0.001(2) C12 0.045(2) 0.078(2) 0.081(3) 0.002(3) -0.014(2) -0.002(2) C13 0.046(2) 0.081(3) 0.070(3) -0.011(2) -0.013(2) 0.012(2) C14 0.045(2) 0.089(3) 0.073(3) 0.007(3) 0.008(2) -0.007(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.224(4) yes O2 C6 1.364(4) yes O2 C14 1.435(3) yes N1 C1 1.358(4) yes N1 C9 1.381(4) yes N2 C13 1.117(6) yes N1 H1 0.9500 no C1 C2 1.455(4) no C2 C3 1.409(5) no C2 C7 1.388(5) no C3 C4 1.374(4) no C4 C5 1.394(5) no C5 C6 1.373(5) no C6 C7 1.412(4) no C7 C8 1.427(5) no C8 C9 1.334(4) no C9 C10 1.506(4) no C10 C11 1.541(5) no C11 C12 1.516(6) no C12 C13 1.501(6) no C3 H2 0.9500 no C4 H3 0.9500 no C5 H4 0.9500 no C8 H5 0.9500 no C10 H6 0.9500 no C10 H7 0.9500 no C11 H8 0.9500 no C11 H9 0.9500 no C12 H10 0.9500 no C12 H11 0.9500 no C14 H12 0.9500 no C14 H13 0.9500 no C14 H14 0.9500 no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C6 O2 C14 117.4(3) yes C1 N1 C9 122.1(2) yes C1 N1 H1 119.00 no C9 N1 H1 119.00 no O1 C1 N1 117.1(2) yes N1 C1 C2 117.7(3) yes O1 C1 C2 125.2(3) yes C1 C2 C7 119.2(3) no C1 C2 C3 119.5(3) no C3 C2 C7 121.3(3) no C2 C3 C4 118.6(3) no C3 C4 C5 121.1(3) no C4 C5 C6 120.1(4) no C5 C6 C7 120.5(3) no O2 C6 C7 115.2(3) yes O2 C6 C5 124.3(3) yes C2 C7 C6 118.4(3) no C2 C7 C8 119.7(3) no C6 C7 C8 121.9(3) no C7 C8 C9 119.6(3) no C8 C9 C10 126.9(3) no N1 C9 C8 121.7(3) yes N1 C9 C10 111.5(2) yes C9 C10 C11 112.8(3) no C10 C11 C12 112.7(3) no C11 C12 C13 112.6(4) no N2 C13 C12 178.0(5) yes C2 C3 H2 120.00 no C4 C3 H2 121.00 no C3 C4 H3 119.00 no C5 C4 H3 120.00 no C4 C5 H4 120.00 no C6 C5 H4 120.00 no C7 C8 H5 120.00 no C9 C8 H5 120.00 no C9 C10 H6 108.00 no C9 C10 H7 109.00 no C11 C10 H6 108.00 no C11 C10 H7 109.00 no H6 C10 H7 109.00 no C10 C11 H8 109.00 no C10 C11 H9 108.00 no C12 C11 H8 108.00 no C12 C11 H9 109.00 no H8 C11 H9 109.00 no C11 C12 H10 108.00 no C11 C12 H11 109.00 no C13 C12 H10 108.00 no C13 C12 H11 109.00 no H10 C12 H11 110.00 no O2 C14 H12 109.00 no O2 C14 H13 109.00 no O2 C14 H14 111.00 no H12 C14 H13 110.00 no H12 C14 H14 109.00 no H13 C14 H14 108.00 no 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 _geom_torsion_publ_flag C14 O2 C6 C5 -0.7(5) no C14 O2 C6 C7 178.2(3) no C9 N1 C1 O1 -179.3(3) no C9 N1 C1 C2 1.9(5) no C1 N1 C9 C8 -0.6(5) no C1 N1 C9 C10 -179.9(3) no O1 C1 C2 C3 -0.9(6) no O1 C1 C2 C7 179.3(3) no N1 C1 C2 C3 177.8(3) no N1 C1 C2 C7 -2.0(5) no C1 C2 C3 C4 178.9(3) no C7 C2 C3 C4 -1.4(5) no C1 C2 C7 C6 -179.3(3) no C1 C2 C7 C8 0.8(5) no C3 C2 C7 C6 0.9(5) no C3 C2 C7 C8 -179.0(3) no C2 C3 C4 C5 1.4(6) no C3 C4 C5 C6 -1.0(6) no C4 C5 C6 O2 179.4(3) no C4 C5 C6 C7 0.6(5) no O2 C6 C7 C2 -179.4(3) no O2 C6 C7 C8 0.4(5) no C5 C6 C7 C2 -0.5(5) no C5 C6 C7 C8 179.3(3) no C2 C7 C8 C9 0.4(5) no C6 C7 C8 C9 -179.4(3) no C7 C8 C9 N1 -0.6(5) no C7 C8 C9 C10 178.6(3) no N1 C9 C10 C11 -55.5(4) no C8 C9 C10 C11 125.3(4) no C9 C10 C11 C12 177.0(3) no C10 C11 C12 C13 65.3(5) no 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_publ_flag C11 H8 N1 0.9500 2.5800 2.899(5) 100.00 yes