#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/25/2012588.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_2012588 loop_ _publ_author_name 'Subbiah Pandi, A.' 'Rajakannan, V.' 'Velmurugan, D.' 'Parvez, Masood' 'Kim, Moon-Jib' 'Senthilvelan, A.' 'Narasinga Rao, S.' _publ_section_title ; Three tetrahydroisoquinolinedione derivatives ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o164 _journal_page_last o167 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C16 H12 Br1 N1 O2' _chemical_formula_structural 'C16 H12 Br1 N1 O2' _chemical_formula_sum 'C16 H12 Br N O2' _chemical_formula_weight 330.18 _chemical_name_systematic ; N-(2-Bromo-4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 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 _cell_angle_beta 94.750(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.847(2) _cell_length_b 7.9190(7) _cell_length_c 11.0602(11) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 10.2 _cell_measurement_theta_min 5.0 _cell_volume 1383.2(3) _computing_cell_refinement 'CAD-4 EXPRESS' _computing_data_collection 'CAD-4 EXPRESS (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD-4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1997)' _computing_publication_material 'SHELXL97 and PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf-Nonius FR-590' _diffrn_measurement_method 'non-profiled \w/2\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .019 _diffrn_reflns_av_sigmaI/netI .029 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2554 _diffrn_reflns_theta_full 24.97 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 2.2 _diffrn_standards_decay_% 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 2.972 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 664 _exptl_crystal_size_max .35 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .30 _refine_diff_density_max .59 _refine_diff_density_min -.83 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 2421 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.017 _refine_ls_R_factor_all .068 _refine_ls_R_factor_gt .042 _refine_ls_shift/su_max .002 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .114 _refine_ls_wR_factor_ref .126 _reflns_number_gt 1818 _reflns_number_total 2421 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file na1552.cif _[local]_cod_data_source_block II _[local]_cod_cif_authors_sg_H-M 'P 21/n' _[local]_cod_chemical_formula_sum_orig 'C16 H12 Br1 N1 O2' _cod_database_code 2012588 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Br1 .18497(3) .23293(5) .67278(4) .0643(2) Uani d . 1 . . Br N1 .15445(17) .1708(4) .9412(3) .0396(7) Uani d . 1 . . N O1 .03927(15) .3324(3) .8949(2) .0502(7) Uani d . 1 . . O O2 .26553(19) .0036(4) .9991(3) .0748(10) Uani d . 1 . . O C1 .1095(2) .3218(4) .9440(3) .0377(8) Uani d . 1 . . C C2 .1520(2) .4689(5) 1.0072(4) .0481(9) Uani d . 1 . . C H2A .1132 .5169 1.0611 .058 Uiso calc R 1 . . H H2B .1616 .5538 .9467 .058 Uiso calc R 1 . . H C3 .2748(2) .5659(5) 1.1457(4) .0536(10) Uani d . 1 . . C H3 .2505 .6727 1.1456 .064 Uiso calc R 1 . . H C4 .3506(2) .5368(7) 1.2113(4) .0645(12) Uani d . 1 . . C H4 .3774 .6242 1.2557 .077 Uiso calc R 1 . . H C5 .3873(2) .3804(7) 1.2121(4) .0606(12) Uani d . 1 . . C H5 .4386 .3618 1.2571 .073 Uiso calc R 1 . . H C6 .3485(3) .2511(5) 1.1468(4) .0533(10) Uani d . 1 . . C H6 .3736 .1449 1.1471 .064 Uiso calc R 1 . . H C7 .2332(2) .1397(5) 1.0058(3) .0459(9) Uani d . 1 . . C C8 .2714(2) .2792(5) 1.0797(3) .0413(8) Uani d . 1 . . C C9 .2346(2) .4363(5) 1.0797(3) .0406(8) Uani d . 1 . . C C10 .1205(2) .0402(4) .8621(3) .0391(8) Uani d . 1 . . C C11 .1288(2) .0497(5) .7388(3) .0425(8) Uani d . 1 . . C C12 .0964(2) -.0765(5) .6620(4) .0495(9) Uani d . 1 . . C H12 .1023 -.0688 .5792 .059 Uiso calc R 1 . . H C13 .0555(2) -.2129(5) .7065(4) .0502(9) Uani d . 1 . . C C14 .0476(2) -.2220(4) .8305(4) .0491(9) Uani d . 1 . . C H14 .0205 -.3144 .8620 .059 Uiso calc R 1 . . H C15 .0791(2) -.0966(4) .9071(4) .0453(9) Uani d . 1 . . C H15 .0725 -.1039 .9897 .054 Uiso calc R 1 . . H C16 .0203(3) -.3502(6) .6226(5) .0729(13) Uani d . 1 . . C H16A -.0331 -.3144 .5834 .109 Uiso calc R 1 . . H H16B .0122 -.4510 .6685 .109 Uiso calc R 1 . . H H16C .0592 -.3725 .5625 .109 Uiso calc R 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 Br1 .0802(4) .0542(3) .0610(3) -.0184(2) .0208(2) -.0017(2) N1 .0401(16) .0360(15) .0415(16) .0036(13) -.0045(13) -.0057(13) O1 .0405(15) .0467(15) .0611(17) .0058(12) -.0096(13) -.0079(13) O2 .0702(19) .0551(18) .094(2) .0302(15) -.0255(17) -.0209(16) C1 .0379(19) .0358(17) .0388(19) .0019(15) -.0015(16) -.0025(15) C2 .042(2) .0380(19) .062(3) .0027(16) -.0102(17) -.0098(18) C3 .046(2) .056(2) .058(2) -.0056(18) .0012(19) -.010(2) C4 .049(2) .085(3) .059(3) -.014(2) -.006(2) -.019(2) C5 .041(2) .092(3) .046(2) -.006(2) -.0104(18) -.001(2) C6 .041(2) .070(3) .048(2) .0097(19) -.0035(17) .0005(19) C7 .046(2) .046(2) .045(2) .0105(17) -.0027(16) -.0026(17) C8 .0344(18) .052(2) .0373(18) .0039(15) -.0003(15) .0012(16) C9 .0341(17) .048(2) .0392(19) .0005(15) -.0015(14) -.0029(16) C10 .0357(18) .0354(18) .045(2) .0059(14) -.0025(15) -.0032(15) C11 .0406(19) .0405(19) .047(2) -.0015(15) .0058(16) -.0015(16) C12 .055(2) .049(2) .044(2) -.0007(18) .0029(17) -.0082(18) C13 .046(2) .045(2) .060(2) -.0016(17) .0020(18) -.0162(18) C14 .048(2) .0334(18) .065(3) -.0022(16) -.0001(19) .0000(18) C15 .051(2) .0397(19) .045(2) .0079(17) .0002(16) .0064(16) C16 .078(3) .059(3) .081(3) -.020(2) .003(3) -.027(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 C11 . 1.881(4) yes N1 C1 . 1.393(4) yes N1 C7 . 1.407(5) yes N1 C10 . 1.431(4) yes O1 C1 . 1.200(4) yes O2 C7 . 1.198(4) yes C1 C2 . 1.490(5) ? C2 C9 . 1.498(5) ? C2 H2A . .9700 ? C2 H2B . .9700 ? C3 C4 . 1.370(6) ? C3 C9 . 1.385(5) ? C3 H3 . .9300 ? C4 C5 . 1.368(7) ? C4 H4 . .9300 ? C5 C6 . 1.369(6) ? C5 H5 . .9300 ? C6 C8 . 1.394(5) ? C6 H6 . .9300 ? C7 C8 . 1.474(5) ? C8 C9 . 1.374(5) ? C10 C15 . 1.381(5) ? C10 C11 . 1.383(5) ? C11 C12 . 1.383(5) ? C12 C13 . 1.372(5) ? C12 H12 . .9300 ? C13 C14 . 1.389(6) ? C13 C16 . 1.506(6) ? C14 C15 . 1.372(5) ? C14 H14 . .9300 ? C15 H15 . .9300 ? C16 H16A . .9600 ? C16 H16B . .9600 ? C16 H16C . .9600 ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0030 .0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0060 .0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0110 .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 C1 N1 C7 124.9(3) C1 N1 C10 117.8(3) C7 N1 C10 117.2(3) O1 C1 N1 120.4(3) O1 C1 C2 121.6(3) N1 C1 C2 118.0(3) C1 C2 C9 117.2(3) C1 C2 H2A 108.0 C9 C2 H2A 108.0 C1 C2 H2B 108.0 C9 C2 H2B 108.0 H2A C2 H2B 107.2 C4 C3 C9 120.0(4) C4 C3 H3 120.0 C9 C3 H3 120.0 C5 C4 C3 120.6(4) C5 C4 H4 119.7 C3 C4 H4 119.7 C6 C5 C4 120.1(4) C6 C5 H5 119.9 C4 C5 H5 119.9 C5 C6 C8 119.8(4) C5 C6 H6 120.1 C8 C6 H6 120.1 O2 C7 N1 119.5(3) O2 C7 C8 123.4(3) N1 C7 C8 117.1(3) C9 C8 C6 119.9(3) C9 C8 C7 121.6(3) C6 C8 C7 118.5(3) C8 C9 C3 119.6(3) C8 C9 C2 120.5(3) C3 C9 C2 119.9(3) C15 C10 C11 119.0(3) C15 C10 N1 120.8(3) C11 C10 N1 120.1(3) C10 C11 C12 120.3(3) C10 C11 Br1 120.8(3) C12 C11 Br1 118.9(3) C13 C12 C11 120.8(4) C13 C12 H12 119.6 C11 C12 H12 119.6 C12 C13 C14 118.6(3) C12 C13 C16 120.6(4) C14 C13 C16 120.8(4) C15 C14 C13 120.9(4) C15 C14 H14 119.5 C13 C14 H14 119.5 C14 C15 C10 120.3(4) C14 C15 H15 119.8 C10 C15 H15 119.8 C13 C16 H16A 109.5 C13 C16 H16B 109.5 H16A C16 H16B 109.5 C13 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 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 C6 H6 O2 1 .93 2.53 2.808(5) 98 C5 H5 O1 4_666 .93 2.61 3.451(5) 151 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 C7 N1 C1 O1 -173.2(3) ? C10 N1 C1 O1 10.2(5) ? C7 N1 C1 C2 8.1(5) ? C10 N1 C1 C2 -168.5(3) ? O1 C1 C2 C9 171.9(3) ? N1 C1 C2 C9 -9.4(5) ? C9 C3 C4 C5 .1(7) ? C3 C4 C5 C6 .2(7) ? C4 C5 C6 C8 -.2(6) ? C1 N1 C7 O2 178.3(4) ? C10 N1 C7 O2 -5.1(5) ? C1 N1 C7 C8 -1.4(5) ? C10 N1 C7 C8 175.2(3) ? C5 C6 C8 C9 -.2(6) ? C5 C6 C8 C7 177.2(4) ? O2 C7 C8 C9 176.4(4) ? N1 C7 C8 C9 -4.0(5) ? O2 C7 C8 C6 -1.0(6) ? N1 C7 C8 C6 178.6(3) ? C6 C8 C9 C3 .6(6) ? C7 C8 C9 C3 -176.8(4) ? C6 C8 C9 C2 179.5(4) ? C7 C8 C9 C2 2.2(5) ? C4 C3 C9 C8 -.5(6) ? C4 C3 C9 C2 -179.5(3) ? C1 C2 C9 C8 4.5(5) ? C1 C2 C9 C3 -176.5(3) ? C1 N1 C10 C15 -102.7(4) yes C7 N1 C10 C15 80.4(4) ? C1 N1 C10 C11 77.3(4) ? C7 N1 C10 C11 -99.5(4) ? C15 C10 C11 C12 -.2(5) ? N1 C10 C11 C12 179.7(3) ? C15 C10 C11 Br1 -179.7(2) ? N1 C10 C11 Br1 .2(4) ? C10 C11 C12 C13 .0(6) ? Br1 C11 C12 C13 179.5(3) ? C11 C12 C13 C14 -.2(6) ? C11 C12 C13 C16 -180.0(4) ? C12 C13 C14 C15 .7(6) ? C16 C13 C14 C15 -179.6(4) ? C13 C14 C15 C10 -.9(6) ? C11 C10 C15 C14 .7(5) ? N1 C10 C15 C14 -179.3(3) ?