#------------------------------------------------------------------------------ #$Date: 2015-01-23 12:30:19 +0000 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/71/2007150.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_2007150 loop_ _publ_author_name 'Kandasamy Chinnakali' 'Hoong-Kun Fun' 'Kamaraj Sriraghavan' 'Vaylakkavoor T.Ramakrishnan' _publ_section_title ; 4-Methyl-7,10-dihydrobenzo[h]coumarin and 4-Methyl-7,8,9,10-tetrahydro-8,9-epoxybenzo[h]coumarin ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 542 _journal_page_last 544 _journal_paper_doi 10.1107/S0108270197016508 _journal_volume 54 _journal_year 1998 _chemical_formula_sum 'C14 H12 O2' _chemical_formula_weight 212.24 _chemical_name_systematic ; 4-Methyl-7,10-dihydro-7,8-benzocoumarin ; _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' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 96.781(9) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.2178(8) _cell_length_b 13.3450(10) _cell_length_c 9.7934(9) _cell_measurement_reflns_used 39 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12.42 _cell_measurement_theta_min 5.45 _cell_volume 1066.50(16) _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Siemens P4 diffractometer' _diffrn_measurement_method '\q/2\q 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 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 3194 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.59 _diffrn_standards_decay_% <3 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_meas ? _exptl_crystal_description 'rectangular tablet' _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.133 _refine_diff_density_min -0.115 _refine_ls_extinction_coef 0.0036(14) _refine_ls_extinction_method SHELXL93_(Sheldrick,_1993) _refine_ls_goodness_of_fit_all 0.852 _refine_ls_goodness_of_fit_obs 1.061 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 194 _refine_ls_number_reflns 2451 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.852 _refine_ls_restrained_S_obs 1.061 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_obs .0379 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.0505P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all 0.1039 _refine_ls_wR_factor_obs .0902 _reflns_number_observed 1286 _reflns_number_total 2451 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file cf1186.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 1066.4(2) _cod_database_code 2007150 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_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 O1 .0584(7) .0516(6) .0389(5) -.0003(5) .0069(5) -.0031(5) O11 .1089(11) .0829(9) .0441(6) .0023(8) .0055(7) -.0105(7) C2 .0598(10) .0651(11) .0417(8) -.0073(9) .0027(8) .0025(8) C3 .0595(11) .0632(11) .0502(9) -.0075(9) -.0021(9) .0127(9) C4 .0416(8) .0501(9) .0636(10) -.0066(8) .0047(8) .0123(8) C5 .0555(10) .0434(9) .0685(11) -.0001(8) .0169(8) -.0061(8) C6 .0632(11) .0531(10) .0546(10) -.0088(9) .0182(9) -.0136(8) C7 .0481(9) .0534(10) .0432(8) -.0136(8) .0105(7) -.0024(7) C8 .0423(8) .0436(9) .0433(8) -.0075(7) .0102(7) .0014(6) C9 .0414(8) .0438(8) .0417(8) -.0068(7) .0126(7) -.0024(6) C10 .0416(8) .0418(8) .0548(9) -.0051(7) .0122(7) .0016(7) C12 .0705(13) .0777(13) .0433(9) -.0153(11) .0078(9) -.0012(9) C13 .0751(13) .0745(13) .0481(9) -.0136(11) -.0044(9) .0174(10) C14 .0570(11) .0584(11) .0671(11) -.0001(9) .0030(9) .0161(9) C15 .0514(10) .0505(10) .0520(9) .0007(8) .0120(8) .0053(7) C16 .0661(13) .0574(12) .096(2) .0062(11) .0089(13) .0214(11) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O1 .25121(13) .42615(7) .32124(9) .0495(3) Uani d . 1 . O O11 .1987(2) .39496(10) .09998(11) .0789(4) Uani d . 1 . O C2 .1806(2) .45357(13) .1917(2) .0558(4) Uani d . 1 . C C3 .0935(2) .54661(13) .1794(2) .0583(5) Uani d . 1 . C C4 .0775(2) .60623(12) .2867(2) .0519(4) Uani d . 1 . C C5 .1418(2) .63040(13) .5427(2) .0550(4) Uani d . 1 . C C6 .2158(2) .59644(13) .6656(2) .0561(4) Uani d . 1 . C C7 .3046(2) .50641(12) .67658(15) .0479(4) Uani d . 1 . C C8 .3165(2) .44962(11) .55884(14) .0426(4) Uani d . 1 . C C9 .2372(2) .48586(11) .43436(13) .0417(4) Uani d . 1 . C C10 .1504(2) .57545(11) .42176(15) .0455(4) Uani d . 1 . C C12 .3863(3) .4731(2) .8131(2) .0638(5) Uani d . 1 . C C13 .4845(3) .3822(2) .8107(2) .0668(5) Uani d . 1 . C C14 .4959(2) .32831(15) .6988(2) .0612(5) Uani d . 1 . C C15 .4110(2) .35393(13) .5622(2) .0508(4) Uani d . 1 . C C16 -.0144(3) .7034(2) .2682(3) .0732(6) Uani d . 1 . C H3 .047(2) .5613(12) .0898(19) .069(5) Uiso d . 1 . H H5 .082(2) .6901(13) .5371(17) .070(5) Uiso d . 1 . H H6 .2122(19) .6332(12) .7489(16) .057(5) Uiso d . 1 . H H12A .457(3) .5272(16) .858(2) .098(7) Uiso d . 1 . H H12B .305(3) .4682(16) .878(2) .108(8) Uiso d . 1 . H H13 .544(2) .3602(13) .8931(19) .074(6) Uiso d . 1 . H H14 .567(2) .2698(13) .7008(16) .063(5) Uiso d . 1 . H H15A .331(2) .2960(13) .5254(16) .073(5) Uiso d . 1 . H H15B .489(2) .3538(13) .4967(18) .073(5) Uiso d . 1 . H H16A -.072(3) .7082(19) .173(3) .140(10) Uiso d . 1 . H H16B .061(3) .7572(16) .2962(19) .090(7) Uiso d . 1 . H H16C -.097(3) .7084(18) .335(2) .121(9) Uiso d . 1 . H 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C9 O1 C2 121.24(12) O11 C2 O1 115.7(2) O11 C2 C3 126.9(2) O1 C2 C3 117.30(15) C4 C3 C2 123.1(2) C3 C4 C10 118.8(2) C3 C4 C16 121.0(2) C10 C4 C16 120.3(2) C6 C5 C10 120.7(2) C5 C6 C7 121.8(2) C8 C7 C6 119.27(14) C8 C7 C12 120.8(2) C6 C7 C12 119.9(2) C7 C8 C9 117.53(14) C7 C8 C15 122.32(14) C9 C8 C15 120.15(13) O1 C9 C10 121.05(13) O1 C9 C8 115.17(13) C10 C9 C8 123.78(13) C9 C10 C5 116.85(15) C9 C10 C4 118.59(14) C5 C10 C4 124.6(2) C13 C12 C7 115.1(2) C14 C13 C12 124.0(2) C13 C14 C15 123.6(2) C14 C15 C8 114.0(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 O1 C9 . 1.380(2) ? O1 C2 . 1.381(2) ? O11 C2 . 1.213(2) ? C2 C3 . 1.431(2) ? C3 C4 . 1.337(2) ? C4 C10 . 1.446(2) ? C4 C16 . 1.500(2) ? C5 C6 . 1.361(2) ? C5 C10 . 1.402(2) ? C6 C7 . 1.403(2) ? C7 C8 . 1.393(2) ? C7 C12 . 1.491(2) ? C8 C9 . 1.399(2) ? C8 C15 . 1.493(2) ? C9 C10 . 1.390(2) ? C12 C13 . 1.459(3) ? C13 C14 . 1.324(3) ? C14 C15 . 1.474(2) ? 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 C3 H3 O11 3_565 0.94(2) 2.64(2) 3.509(2) 154.0(10) C12 H12B O11 1_556 0.98(2) 2.62(2) 3.519(2) 152(2) 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 C9 O1 C2 O11 -179.07(14) C9 O1 C2 C3 0.5(2) O11 C2 C3 C4 179.0(2) O1 C2 C3 C4 -0.5(2) C2 C3 C4 C10 -0.3(3) C2 C3 C4 C16 179.7(2) C10 C5 C6 C7 0.7(3) C5 C6 C7 C8 -0.5(2) C5 C6 C7 C12 178.9(2) C6 C7 C8 C9 -0.4(2) C12 C7 C8 C9 -179.74(15) C6 C7 C8 C15 179.03(15) C12 C7 C8 C15 -0.3(2) C2 O1 C9 C10 0.4(2) C2 O1 C9 C8 -179.19(13) C7 C8 C9 O1 -179.26(12) C15 C8 C9 O1 1.3(2) C7 C8 C9 C10 1.2(2) C15 C8 C9 C10 -178.26(14) O1 C9 C10 C5 179.41(13) C8 C9 C10 C5 -1.0(2) O1 C9 C10 C4 -1.2(2) C8 C9 C10 C4 178.32(13) C6 C5 C10 C9 0.1(2) C6 C5 C10 C4 -179.2(2) C3 C4 C10 C9 1.2(2) C16 C4 C10 C9 -178.8(2) C3 C4 C10 C5 -179.5(2) C16 C4 C10 C5 0.5(2) C8 C7 C12 C13 3.5(2) C6 C7 C12 C13 -175.9(2) C7 C12 C13 C14 -3.6(3) C12 C13 C14 C15 0.3(3) C13 C14 C15 C8 2.9(3) C7 C8 C15 C14 -2.8(2) C9 C8 C15 C14 176.55(14)