#------------------------------------------------------------------------------ #$Date: 2015-01-07 16:25:02 +0000 (Wed, 07 Jan 2015) $ #$Revision: 129439 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/49/2204960.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2204960 loop_ _publ_author_name 'Ravikumar, K.' 'Sridhar, B.' 'Mahesh, M.' 'Narayana Reddy, V. V.' _publ_section_title ; A diastereoisomer of furo[3,2-c]quinoline ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o195 _journal_page_last o197 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C17 H16 Cl N O' _chemical_formula_moiety 'C17 H16 Cl N O' _chemical_formula_sum 'C17 H16 Cl N O' _chemical_formula_weight 285.76 _chemical_name_systematic ; 4-(4-chlorophenyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 14.1068(9) _cell_length_b 9.5526(6) _cell_length_c 21.1298(13) _cell_measurement_reflns_used 5262 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 27.858 _cell_measurement_theta_min 2.409 _cell_volume 2847.4(3) _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL-PC (Sheldrick, 1990)' _computing_publication_material 'SHELXL97 and PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_device_type 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method \w _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 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0133 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 30760 _diffrn_reflns_theta_full 28.02 _diffrn_reflns_theta_max 28.02 _diffrn_reflns_theta_min 1.93 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.263 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_meas ? _exptl_crystal_density_method . _exptl_crystal_description needle _exptl_crystal_F_000 1200 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.438 _refine_diff_density_min -0.243 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 185 _refine_ls_number_reflns 3412 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.136 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0564 _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^)+(0.0667P)^2^+0.9682P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1456 _refine_ls_wR_factor_ref 0.1503 _reflns_number_gt 3010 _reflns_number_total 3412 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file rz6035.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2204960 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol Cl1 0.73739(5) 0.13204(8) 0.44457(3) 0.0814(3) Uani d . 1 Cl O1 0.28980(9) 0.10167(16) 0.74049(7) 0.0619(4) Uani d . 1 O N1 0.57431(10) 0.08259(17) 0.74260(7) 0.0457(4) Uani d . 1 N C1 0.43501(15) 0.0678(2) 0.91723(10) 0.0586(5) Uani d . 1 C H1 0.4041 0.0661 0.9561 0.070 Uiso calc R 1 H C2 0.38578(13) 0.0441(2) 0.86199(9) 0.0516(4) Uani d . 1 C H2 0.3210 0.0266 0.8641 0.062 Uiso calc R 1 H C3 0.43004(11) 0.04555(17) 0.80327(8) 0.0416(4) Uani d . 1 C C4 0.37363(11) 0.01643(19) 0.74395(9) 0.0475(4) Uani d . 1 C H4 0.3556 -0.0826 0.7429 0.057 Uiso calc R 1 H C5 0.31865(13) 0.2338(2) 0.71568(12) 0.0623(5) Uani d . 1 C H5A 0.3316 0.2988 0.7499 0.075 Uiso calc R 1 H H5B 0.2689 0.2730 0.6893 0.075 Uiso calc R 1 H C6 0.40784(13) 0.2095(2) 0.67667(10) 0.0566(5) Uani d . 1 C H6A 0.4603 0.2647 0.6928 0.068 Uiso calc R 1 H H6B 0.3974 0.2337 0.6326 0.068 Uiso calc R 1 H C7 0.42753(11) 0.05282(19) 0.68395(8) 0.0436(4) Uani d . 1 C H7 0.3988 0.0028 0.6483 0.052 Uiso calc R 1 H C8 0.53218(10) 0.01237(17) 0.68851(8) 0.0406(4) Uani d . 1 C H8 0.5359 -0.0888 0.6958 0.049 Uiso calc R 1 H C9 0.52748(10) 0.07396(17) 0.80020(8) 0.0396(4) Uani d . 1 C C10 0.57695(13) 0.0977(2) 0.85662(9) 0.0506(4) Uani d . 1 C H10 0.6416 0.1163 0.8553 0.061 Uiso calc R 1 H C11 0.53125(15) 0.0940(2) 0.91392(9) 0.0568(5) Uani d . 1 C H11 0.5654 0.1092 0.9509 0.068 Uiso calc R 1 H C12 0.58525(11) 0.04536(17) 0.62813(8) 0.0415(4) Uani d . 1 C C13 0.58729(16) -0.0527(2) 0.57999(11) 0.0606(5) Uani d . 1 C H13 0.5574 -0.1385 0.5859 0.073 Uiso calc R 1 H C14 0.63258(17) -0.0262(2) 0.52357(10) 0.0659(6) Uani d . 1 C H14 0.6333 -0.0933 0.4917 0.079 Uiso calc R 1 H C15 0.67653(13) 0.0999(2) 0.51499(9) 0.0535(5) Uani d . 1 C C16 0.67550(15) 0.1999(2) 0.56133(10) 0.0600(5) Uani d . 1 C H16 0.7052 0.2857 0.5549 0.072 Uiso calc R 1 H C17 0.62967(14) 0.1720(2) 0.61793(9) 0.0538(5) Uani d . 1 C H17 0.6289 0.2396 0.6496 0.065 Uiso calc R 1 H H1N 0.6370(18) 0.076(2) 0.7445(10) 0.058(6) Uiso d . 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0698(4) 0.1275(6) 0.0469(3) 0.0022(3) 0.0102(2) 0.0009(3) O1 0.0247(5) 0.0870(10) 0.0740(9) -0.0009(6) -0.0033(6) 0.0072(8) N1 0.0254(6) 0.0636(9) 0.0480(8) -0.0038(6) -0.0029(5) -0.0008(7) C1 0.0628(12) 0.0631(12) 0.0499(10) 0.0036(10) 0.0098(9) 0.0102(9) C2 0.0412(9) 0.0531(10) 0.0606(11) -0.0018(8) 0.0073(8) 0.0114(8) C3 0.0325(7) 0.0395(8) 0.0528(9) -0.0019(6) -0.0003(6) 0.0068(7) C4 0.0286(7) 0.0512(10) 0.0627(10) -0.0091(7) -0.0034(7) 0.0021(8) C5 0.0385(9) 0.0689(13) 0.0795(14) 0.0091(9) -0.0062(9) -0.0033(11) C6 0.0413(9) 0.0584(11) 0.0702(12) 0.0083(8) -0.0002(8) 0.0135(9) C7 0.0299(7) 0.0516(9) 0.0495(9) -0.0055(6) -0.0075(6) -0.0022(7) C8 0.0331(7) 0.0390(8) 0.0498(9) -0.0006(6) -0.0032(6) -0.0003(7) C9 0.0312(7) 0.0393(8) 0.0483(9) 0.0007(6) -0.0032(6) 0.0039(7) C10 0.0393(8) 0.0592(11) 0.0533(10) -0.0010(8) -0.0082(7) 0.0041(8) C11 0.0611(11) 0.0611(11) 0.0480(10) 0.0029(9) -0.0096(8) 0.0045(8) C12 0.0337(7) 0.0423(8) 0.0484(9) 0.0054(6) -0.0030(6) -0.0022(7) C13 0.0674(12) 0.0455(10) 0.0689(13) -0.0013(9) 0.0050(10) -0.0115(9) C14 0.0741(14) 0.0672(13) 0.0564(12) 0.0077(11) 0.0047(10) -0.0206(10) C15 0.0413(9) 0.0751(13) 0.0441(9) 0.0100(9) 0.0011(7) 0.0004(8) C16 0.0617(12) 0.0606(12) 0.0577(11) -0.0101(9) 0.0089(9) 0.0004(9) C17 0.0580(11) 0.0529(10) 0.0505(10) -0.0098(8) 0.0084(8) -0.0091(8) 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 C5 O1 C4 106.58(13) C9 N1 C8 117.91(13) C9 N1 H1N 115.5(14) C8 N1 H1N 114.3(14) C2 C1 C11 118.83(18) C2 C1 H1 120.6 C11 C1 H1 120.6 C1 C2 C3 121.93(17) C1 C2 H2 119.0 C3 C2 H2 119.0 C2 C3 C9 118.93(16) C2 C3 C4 120.17(15) C9 C3 C4 120.90(15) O1 C4 C3 111.80(15) O1 C4 C7 103.87(14) C3 C4 C7 112.76(13) O1 C4 H4 109.4 C3 C4 H4 109.4 C7 C4 H4 109.4 O1 C5 C6 107.46(16) O1 C5 H5A 110.2 C6 C5 H5A 110.2 O1 C5 H5B 110.2 C6 C5 H5B 110.2 H5A C5 H5B 108.5 C5 C6 C7 104.16(16) C5 C6 H6A 110.9 C7 C6 H6A 110.9 C5 C6 H6B 110.9 C7 C6 H6B 110.9 H6A C6 H6B 108.9 C4 C7 C8 111.90(14) C4 C7 C6 102.54(14) C8 C7 C6 115.38(14) C4 C7 H7 108.9 C8 C7 H7 108.9 C6 C7 H7 108.9 N1 C8 C12 111.41(13) N1 C8 C7 109.15(13) C12 C8 C7 111.85(13) N1 C8 H8 108.1 C12 C8 H8 108.1 C7 C8 H8 108.1 N1 C9 C10 120.01(14) N1 C9 C3 121.25(15) C10 C9 C3 118.72(16) C11 C10 C9 120.86(16) C11 C10 H10 119.6 C9 C10 H10 119.6 C10 C11 C1 120.72(18) C10 C11 H11 119.6 C1 C11 H11 119.6 C17 C12 C13 118.00(17) C17 C12 C8 122.65(15) C13 C12 C8 119.32(16) C14 C13 C12 121.49(19) C14 C13 H13 119.3 C12 C13 H13 119.3 C15 C14 C13 119.18(18) C15 C14 H14 120.4 C13 C14 H14 120.4 C14 C15 C16 121.04(18) C14 C15 Cl1 119.42(16) C16 C15 Cl1 119.51(17) C15 C16 C17 119.21(19) C15 C16 H16 120.4 C17 C16 H16 120.4 C12 C17 C16 121.07(18) C12 C17 H17 119.5 C16 C17 H17 119.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C15 1.7450(19) y O1 C5 1.426(3) y O1 C4 1.438(2) y N1 C9 1.387(2) y N1 C8 1.452(2) y N1 H1N 0.89(3) ? C1 C2 1.377(3) ? C1 C11 1.382(3) ? C1 H1 0.9300 ? C2 C3 1.389(2) ? C2 H2 0.9300 ? C3 C9 1.403(2) ? C3 C4 1.510(2) ? C4 C7 1.519(2) ? C4 H4 0.9800 ? C5 C6 1.522(3) ? C5 H5A 0.9700 ? C5 H5B 0.9700 ? C6 C7 1.530(3) ? C6 H6A 0.9700 ? C6 H6B 0.9700 ? C7 C8 1.529(2) ? C7 H7 0.9800 ? C8 C12 1.512(2) ? C8 H8 0.9800 ? C9 C10 1.400(2) ? C10 C11 1.372(3) ? C10 H10 0.9300 ? C11 H11 0.9300 ? C12 C17 1.379(2) ? C12 C13 1.383(3) ? C13 C14 1.376(3) ? C13 H13 0.9300 ? C14 C15 1.367(3) ? C14 H14 0.9300 ? C15 C16 1.368(3) ? C16 C17 1.386(3) ? C16 H16 0.9300 ? C17 H17 0.9300 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1N O1 6_657 0.89(3) 2.19(3) 3.066(2) 168(2) C6 H6A N1 . 0.97 2.60 2.988(2) 105 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 C11 C1 C2 C3 0.1(3) C1 C2 C3 C9 -0.9(3) C1 C2 C3 C4 178.88(18) C5 O1 C4 C3 82.63(18) C5 O1 C4 C7 -39.23(19) C2 C3 C4 O1 51.0(2) C9 C3 C4 O1 -129.20(16) C2 C3 C4 C7 167.60(16) C9 C3 C4 C7 -12.6(2) C4 O1 C5 C6 25.6(2) O1 C5 C6 C7 -1.8(2) O1 C4 C7 C8 160.88(14) C3 C4 C7 C8 39.7(2) O1 C4 C7 C6 36.64(16) C3 C4 C7 C6 -84.58(17) C5 C6 C7 C4 -20.90(18) C5 C6 C7 C8 -142.80(17) C9 N1 C8 C12 173.43(14) C9 N1 C8 C7 49.4(2) C4 C7 C8 N1 -57.68(18) C6 C7 C8 N1 59.05(19) C4 C7 C8 C12 178.58(14) C6 C7 C8 C12 -64.70(19) C8 N1 C9 C10 159.12(16) C8 N1 C9 C3 -22.7(2) C2 C3 C9 N1 -177.22(16) C4 C3 C9 N1 3.0(2) C2 C3 C9 C10 1.0(2) C4 C3 C9 C10 -178.84(16) N1 C9 C10 C11 177.95(17) C3 C9 C10 C11 -0.3(3) C9 C10 C11 C1 -0.6(3) C2 C1 C11 C10 0.6(3) N1 C8 C12 C17 -32.0(2) C7 C8 C12 C17 90.48(19) N1 C8 C12 C13 150.18(17) C7 C8 C12 C13 -87.35(19) C17 C12 C13 C14 0.4(3) C8 C12 C13 C14 178.35(18) C12 C13 C14 C15 0.0(3) C13 C14 C15 C16 -0.4(3) C13 C14 C15 Cl1 177.92(17) C14 C15 C16 C17 0.5(3) Cl1 C15 C16 C17 -177.90(16) C13 C12 C17 C16 -0.4(3) C8 C12 C17 C16 -178.25(18) C15 C16 C17 C12 0.0(3) _cod_database_fobs_code 2204960 _journal_paper_doi 10.1107/S1600536804033550