#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2008588.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_2008588 loop_ _publ_author_name 'Chinnakali, K.' 'Fun, H.-K.' 'Sriraghavan, K.' 'Ramakrishnan, V. T.' _publ_section_title ; 9-Hydroxy-8-iodo-4-methyl-7,8,9,10-tetrahydrobenzo[h]coumarin ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 946 _journal_page_last 948 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C14 H13 I O3' _chemical_formula_weight 356.14 _chemical_name_systematic ; 9-hydroxy-8-iodo-4-methyl-7,8,9,10-tetrahydro-7,8-benzocoumarin ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 104.2300(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.49310(10) _cell_length_b 22.2521(3) _cell_length_c 11.0350(2) _cell_measurement_reflns_used 2021 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.99 _cell_measurement_theta_min 2.64 _cell_volume 1307.45(4) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and PARST (Nardelli, 1995)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measurement_device ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\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 0.021 _diffrn_reflns_av_sigmaI/netI 0.025 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 8143 _diffrn_reflns_theta_max 26.99 _diffrn_reflns_theta_min 2.64 _exptl_absorpt_coefficient_mu 2.446 _exptl_absorpt_correction_T_max 0.415 _exptl_absorpt_correction_T_min 0.361 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; empirical (SADABS; Sheldrick, 1997) ; _exptl_crystal_colour 'light brown' _exptl_crystal_density_diffrn 1.809 _exptl_crystal_density_method 'not measured' _exptl_crystal_description parallelepiped _exptl_crystal_F_000 696 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.36 _refine_diff_density_max 1.03 _refine_diff_density_min -1.08 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.208 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 165 _refine_ls_number_reflns 2824 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.208 _refine_ls_R_factor_all 0.060 _refine_ls_R_factor_gt 0.053 _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^)+(0.0530P)^2^+4.5488P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.151 _reflns_number_gt 2463 _reflns_number_total 2824 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file na1400.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2008588 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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_type_symbol I1 0.10963(9) 0.44208(2) 0.36910(5) 0.0661(2) Uani d . 1 I O1 0.8061(7) 0.29106(16) 0.0041(4) 0.0412(8) Uani d . 1 O C2 0.9557(11) 0.2687(3) -0.0675(6) 0.0467(13) Uani d . 1 C C3 0.9369(12) 0.2966(3) -0.1867(6) 0.0488(14) Uani d . 1 C H3 1.0371 0.2820 -0.2368 0.059 Uiso calc R 1 H C4 0.7806(12) 0.3433(3) -0.2302(5) 0.0475(13) Uani d . 1 C C5 0.4648(13) 0.4169(3) -0.1800(6) 0.0507(14) Uani d . 1 C H5 0.4476 0.4369 -0.2557 0.061 Uiso calc R 1 H C6 0.3343(12) 0.4360(3) -0.0978(6) 0.0506(14) Uani d . 1 C H6 0.2275 0.4689 -0.1189 0.061 Uiso calc R 1 H C7 0.3555(10) 0.4079(2) 0.0179(5) 0.0408(11) Uani d . 1 C C8 0.5083(10) 0.3577(2) 0.0494(5) 0.0374(11) Uani d . 1 C C9 0.6438(10) 0.3392(2) -0.0362(5) 0.0368(11) Uani d . 1 C C10 0.6280(11) 0.3664(2) -0.1515(5) 0.0420(12) Uani d . 1 C O11 1.0953(9) 0.2281(2) -0.0213(5) 0.0587(11) Uani d . 1 O C12 0.2125(11) 0.4320(3) 0.1101(6) 0.0456(13) Uani d . 1 C H12A 0.2125 0.4756 0.1078 0.055 Uiso calc R 1 H H12B 0.0394 0.4185 0.0851 0.055 Uiso calc R 1 H C13 0.3280(11) 0.4112(3) 0.2414(6) 0.0467(13) Uani d . 1 C H13 0.4965 0.4286 0.2681 0.056 Uiso calc R 1 H C14 0.3540(11) 0.3428(3) 0.2479(5) 0.0434(12) Uani d . 1 C H14 0.1898 0.3245 0.2119 0.052 Uiso calc R 1 H C15 0.5373(10) 0.3241(2) 0.1710(5) 0.0397(11) Uani d . 1 C H15A 0.7072 0.3300 0.2212 0.048 Uiso calc R 1 H H15B 0.5158 0.2815 0.1527 0.048 Uiso calc R 1 H O16 0.4509(8) 0.3195(2) 0.3674(4) 0.0540(11) Uani d . 1 O H16 0.3351 0.3099 0.3981 0.081 Uiso calc R 1 H C17 0.7711(19) 0.3711(4) -0.3545(7) 0.074(2) Uani d . 1 C H17A 0.8840 0.3502 -0.3939 0.110 Uiso calc R 1 H H17B 0.8200 0.4126 -0.3432 0.110 Uiso calc R 1 H H17C 0.6033 0.3685 -0.4064 0.110 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 I1 0.0643(3) 0.0663(3) 0.0735(4) 0.0078(2) 0.0280(2) -0.0052(2) O1 0.046(2) 0.0357(18) 0.042(2) 0.0059(16) 0.0106(16) -0.0024(15) C2 0.050(3) 0.041(3) 0.053(3) -0.006(2) 0.019(3) -0.011(2) C3 0.061(4) 0.043(3) 0.048(3) -0.011(3) 0.024(3) -0.012(2) C4 0.064(4) 0.039(3) 0.039(3) -0.015(3) 0.011(3) -0.009(2) C5 0.065(4) 0.047(3) 0.038(3) 0.001(3) 0.009(3) 0.010(2) C6 0.053(3) 0.037(3) 0.056(4) 0.007(2) 0.004(3) 0.007(2) C7 0.038(3) 0.032(2) 0.050(3) -0.002(2) 0.006(2) 0.000(2) C8 0.036(2) 0.033(2) 0.041(3) -0.002(2) 0.006(2) -0.002(2) C9 0.039(3) 0.029(2) 0.039(3) -0.0040(19) 0.004(2) -0.004(2) C10 0.052(3) 0.035(3) 0.036(3) -0.007(2) 0.006(2) -0.006(2) O11 0.065(3) 0.049(2) 0.070(3) 0.013(2) 0.030(2) 0.000(2) C12 0.040(3) 0.039(3) 0.058(3) 0.005(2) 0.014(3) 0.000(2) C13 0.038(3) 0.046(3) 0.058(3) 0.002(2) 0.014(2) -0.006(3) C14 0.039(3) 0.041(3) 0.049(3) -0.002(2) 0.009(2) 0.002(2) C15 0.043(3) 0.034(2) 0.044(3) 0.004(2) 0.012(2) 0.004(2) O16 0.047(2) 0.070(3) 0.047(2) 0.000(2) 0.0151(18) 0.013(2) C17 0.118(7) 0.063(4) 0.044(4) -0.002(4) 0.028(4) -0.003(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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 _geom_angle_publ_flag C2 O1 C9 121.6(5) ? O11 C2 O1 115.8(6) yes O11 C2 C3 127.1(6) yes O1 C2 C3 117.0(5) ? C4 C3 C2 123.5(6) ? C4 C3 H3 118.3 ? C2 C3 H3 118.3 ? C3 C4 C10 118.1(5) ? C3 C4 C17 121.2(6) ? C10 C4 C17 120.7(6) ? C6 C5 C10 120.5(5) ? C6 C5 H5 119.7 ? C10 C5 H5 119.7 ? C5 C6 C7 122.0(5) ? C5 C6 H6 119.0 ? C7 C6 H6 119.0 ? C8 C7 C6 119.8(6) ? C8 C7 C12 119.6(5) ? C6 C7 C12 120.6(5) ? C7 C8 C9 117.1(5) ? C7 C8 C15 123.1(5) ? C9 C8 C15 119.8(5) ? C10 C9 O1 121.0(5) ? C10 C9 C8 124.4(5) ? O1 C9 C8 114.5(5) yes C9 C10 C5 116.0(5) ? C9 C10 C4 118.7(5) ? C5 C10 C4 125.2(5) yes C13 C12 C7 111.6(5) ? C13 C12 H12A 109.3 ? C7 C12 H12A 109.3 ? C13 C12 H12B 109.3 ? C7 C12 H12B 109.3 ? H12A C12 H12B 108.0 ? C12 C13 C14 111.4(5) ? C12 C13 I1 110.9(4) ? C14 C13 I1 110.2(4) ? C12 C13 H13 108.1 ? C14 C13 H13 108.1 ? I1 C13 H13 108.1 ? O16 C14 C15 105.9(4) ? O16 C14 C13 115.1(5) ? C15 C14 C13 108.2(5) ? O16 C14 H14 109.2 ? C15 C14 H14 109.2 ? C13 C14 H14 109.2 ? C8 C15 C14 114.8(4) ? C8 C15 H15A 108.6 ? C14 C15 H15A 108.6 ? C8 C15 H15B 108.6 ? C14 C15 H15B 108.6 ? H15A C15 H15B 107.5 ? C14 O16 H16 109.5 ? C4 C17 H17A 109.5 ? C4 C17 H17B 109.5 ? H17A C17 H17B 109.5 ? C4 C17 H17C 109.5 ? H17A C17 H17C 109.5 ? H17B C17 H17C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag I1 C13 2.175(6) yes O1 C2 1.366(7) ? O1 C9 1.395(6) ? C2 O11 1.214(8) ? C2 C3 1.435(9) ? C3 C4 1.357(9) yes C3 H3 0.9300 ? C4 C10 1.442(8) ? C4 C17 1.495(9) ? C5 C6 1.356(10) yes C5 C10 1.424(8) ? C5 H5 0.9300 ? C6 C7 1.401(9) ? C6 H6 0.9300 ? C7 C8 1.390(7) ? C7 C12 1.528(8) yes C8 C9 1.400(8) ? C8 C15 1.509(7) yes C9 C10 1.393(8) ? C12 C13 1.505(9) yes C12 H12A 0.9700 ? C12 H12B 0.9700 ? C13 C14 1.527(8) yes C13 H13 0.9800 ? C14 O16 1.395(7) yes C14 C15 1.526(8) yes C14 H14 0.9800 ? C15 H15A 0.9700 ? C15 H15B 0.9700 ? O16 H16 0.8200 ? C17 H17A 0.9600 ? C17 H17B 0.9600 ? C17 H17C 0.9600 ? 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 _geom_hbond_publ_flag O16 H16 O11 4_455 0.82 1.95 2.761(7) 168 yes 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 C9 O1 C2 O11 177.7(5) ? C9 O1 C2 C3 -0.5(7) ? O11 C2 C3 C4 -177.9(6) ? O1 C2 C3 C4 0.1(8) ? C2 C3 C4 C10 0.8(9) ? C2 C3 C4 C17 179.2(6) ? C10 C5 C6 C7 0.7(10) ? C5 C6 C7 C8 -2.0(9) ? C5 C6 C7 C12 177.9(6) ? C6 C7 C8 C9 2.7(8) ? C12 C7 C8 C9 -177.1(5) ? C6 C7 C8 C15 -178.8(5) ? C12 C7 C8 C15 1.3(8) yes C2 O1 C9 C10 0.1(7) ? C2 O1 C9 C8 -178.5(5) ? C7 C8 C9 C10 -2.5(8) ? C15 C8 C9 C10 179.0(5) ? C7 C8 C9 O1 176.0(4) ? C15 C8 C9 O1 -2.5(7) ? O1 C9 C10 C5 -177.1(5) ? C8 C9 C10 C5 1.3(8) ? O1 C9 C10 C4 0.9(7) ? C8 C9 C10 C4 179.3(5) ? C6 C5 C10 C9 -0.3(9) ? C6 C5 C10 C4 -178.2(6) ? C3 C4 C10 C9 -1.3(8) ? C17 C4 C10 C9 -179.7(6) ? C3 C4 C10 C5 176.5(6) ? C17 C4 C10 C5 -1.9(9) ? C8 C7 C12 C13 20.6(7) yes C6 C7 C12 C13 -159.3(5) ? C7 C12 C13 C14 -53.9(6) yes C7 C12 C13 I1 -177.0(4) ? C12 C13 C14 O16 -177.7(5) ? I1 C13 C14 O16 -54.2(6) ? C12 C13 C14 C15 64.2(6) yes I1 C13 C14 C15 -172.3(4) ? C7 C8 C15 C14 9.7(7) yes C9 C8 C15 C14 -171.9(5) ? O16 C14 C15 C8 -164.6(5) ? C13 C14 C15 C8 -40.7(6) yes