#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/01/2200143.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_2200143 loop_ _publ_author_name 'Vijayalakshmi, L ' 'Parthasarathi, V ' 'Varu, Bharat' 'Shah, Anamik' _publ_section_title ; 3-Cyano-4-[2-(4-methoxyphenyl)ethenyl]-6-methyl-2H-1-benzopyran-2-one ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o245 _journal_page_last o246 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C20 H15 N O3' _chemical_formula_moiety 'C20 H15 N O3' _chemical_formula_sum 'C20 H15 N O3' _chemical_formula_weight 317.33 _chemical_name_common 2-(3-cyano-6-methylcoumarin-4-yl)-1-(4-methoxyphenyl)ethene _chemical_name_systematic ; 3-cyano-4-[2-(4-methoxyphenyl)ethenyl]-6-methyl-2H-1-benzopyran-2-one ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.8683(12) _cell_length_b 7.913(2) _cell_length_c 26.0869(11) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25 _cell_measurement_theta_min 2 _cell_volume 1624.2(5) _computing_cell_refinement 'MolEN (Fair, 1990)' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction MolEN _computing_molecular_graphics 'ZORTEP97 (Zsolnai, 1997)' _computing_publication_material 'SHELXL97 and PARST95 (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .999 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54175 _diffrn_reflns_av_R_equivalents .000 _diffrn_reflns_av_sigmaI/netI .012 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1805 _diffrn_reflns_theta_full 69.84 _diffrn_reflns_theta_max 69.84 _diffrn_reflns_theta_min 3.39 _diffrn_standards_decay_% .058 _diffrn_standards_interval_count 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .712 _exptl_absorpt_correction_T_max .930 _exptl_absorpt_correction_T_min .875 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 664 _exptl_crystal_size_max .20 _exptl_crystal_size_mid .12 _exptl_crystal_size_min .10 _refine_diff_density_max .26 _refine_diff_density_min -.20 _refine_ls_extinction_coef .0079(11) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.17 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 222 _refine_ls_number_reflns 1804 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.17 _refine_ls_R_factor_all .057 _refine_ls_R_factor_gt .051 _refine_ls_shift/su_max .009 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0837P)^2^+0.2613P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .144 _reflns_number_gt 1626 _reflns_number_total 1804 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ci6005.cif _[local]_cod_data_source_block 1 _cod_original_cell_volume 1624.1(5) _cod_database_code 2200143 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, 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 O1 .5438(3) .1758(3) .12170(9) .0672(7) Uani d . 1 . . O O2 .3666(3) .0550(4) .17594(13) .0942(10) Uani d . 1 . . O C2 .5083(4) .1108(4) .16893(15) .0649(9) Uani d . 1 . . C C3 .6427(4) .1127(4) .20688(12) .0536(7) Uani d . 1 . . C C4 .8000(4) .1806(4) .19728(11) .0475(6) Uani d . 1 . . C C5 .9887(4) .3146(4) .13108(12) .0529(7) Uani d . 1 . . C H5 1.0766 .3215 .1548 .067(4) Uiso calc R 1 . . H C6 1.0157(5) .3723(4) .08248(12) .0604(8) Uani d . 1 . . C C7 .8824(5) .3648(5) .04749(13) .0697(10) Uani d . 1 . . C H7 .8988 .4041 .0143 .067(4) Uiso calc R 1 . . H C8 .7263(5) .3001(5) .06136(13) .0681(9) Uani d . 1 . . C H8 .6377 .2967 .0378 .067(4) Uiso calc R 1 . . H C9 .7032(4) .2410(4) .11011(13) .0557(8) Uani d . 1 . . C C10 .8323(4) .2450(4) .14645(11) .0482(7) Uani d . 1 . . C C11 .9320(3) .1890(4) .23647(11) .0499(7) Uani d . 1 . . C H11 1.0412 .1533 .2282 .067(4) Uiso calc R 1 . . H C12 .9023(4) .2455(4) .28332(11) .0496(7) Uani d . 1 . . C H12 .7910 .2776 .2904 .067(4) Uiso calc R 1 . . H C13 .9767(4) .3503(4) .36948(11) .0515(7) Uani d . 1 . . C H13 .8686 .3973 .3713 .067(4) Uiso calc R 1 . . H C14 1.0833(4) .3690(4) .41012(12) .0567(8) Uani d . 1 . . C H14 1.0475 .4263 .4393 .067(4) Uiso calc R 1 . . H C15 1.2475(4) .3010(4) .40758(11) .0530(7) Uani d . 1 . . C C16 1.2980(4) .2143(4) .36462(11) .0537(7) Uani d . 1 . . C H16 1.4065 .1679 .3631 .067(4) Uiso calc R 1 . . H C17 1.1884(4) .1956(4) .32378(11) .0518(7) Uani d . 1 . . C H17 1.2242 .1372 .2948 .067(4) Uiso calc R 1 . . H C18 1.0237(4) .2633(4) .32530(11) .0473(6) Uani d . 1 . . C O19 1.3445(3) .3271(4) .45007(8) .0732(7) Uani d . 1 . . O C20 1.5138(5) .2619(7) .44906(15) .0834(12) Uani d . 1 . . C H201 1.5107 .1434 .4413 .123(8) Uiso calc R 1 . . H H202 1.5660 .2786 .4819 .123(8) Uiso calc R 1 . . H H203 1.5783 .3200 .4233 .123(8) Uiso calc R 1 . . H C21 .5997(4) .0334(5) .25419(15) .0645(9) Uani d . 1 . . C N21 .5661(5) -.0349(5) .29175(15) .0883(10) Uani d . 1 . . N C22 1.1854(5) .4455(6) .06776(15) .0783(11) Uani d . 1 . . C H221 1.2285 .5125 .0955 .123(8) Uiso calc R 1 . . H H222 1.1724 .5151 .0379 .123(8) Uiso calc R 1 . . H H223 1.2635 .3555 .0605 .123(8) 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 O1 .0383(11) .0745(14) .0888(16) -.0068(11) -.0153(10) -.0109(13) O2 .0425(13) .098(2) .142(2) -.0279(15) -.0157(15) .0056(19) C2 .0411(16) .0581(18) .096(2) -.0096(15) -.0065(17) -.0073(17) C3 .0366(14) .0476(15) .0765(19) -.0042(13) -.0016(14) -.0058(14) C4 .0348(13) .0418(13) .0658(16) -.0007(12) -.0022(12) -.0061(12) C5 .0412(14) .0519(15) .0654(16) -.0036(14) -.0017(14) -.0053(13) C6 .0595(19) .0605(17) .0611(17) -.0042(17) .0021(15) -.0052(15) C7 .080(2) .074(2) .0556(17) -.001(2) -.0048(17) -.0017(16) C8 .061(2) .076(2) .068(2) .0018(19) -.0197(16) -.0107(17) C9 .0421(15) .0526(16) .0723(18) -.0002(14) -.0083(14) -.0116(14) C10 .0380(14) .0471(14) .0595(15) .0001(13) -.0050(12) -.0111(12) C11 .0313(12) .0528(15) .0657(16) -.0014(12) -.0017(12) .0004(14) C12 .0361(13) .0492(14) .0634(16) .0004(13) .0001(12) .0022(12) C13 .0431(14) .0548(15) .0566(15) .0070(13) .0054(13) .0035(13) C14 .0567(18) .0570(17) .0563(15) .0134(16) .0064(15) -.0019(14) C15 .0520(16) .0559(16) .0510(14) .0032(15) -.0057(13) .0057(13) C16 .0413(14) .0578(16) .0618(17) .0082(14) .0003(13) .0047(13) C17 .0413(14) .0567(16) .0576(15) .0069(14) .0025(13) -.0060(13) C18 .0383(13) .0454(13) .0581(15) .0005(12) .0014(12) .0040(12) O19 .0648(15) .0912(17) .0638(13) .0191(15) -.0148(11) -.0054(12) C20 .058(2) .107(3) .085(2) .013(2) -.0243(19) .000(2) C21 .0432(16) .0580(17) .092(2) -.0076(16) .0087(17) -.0055(18) N21 .073(2) .081(2) .111(2) -.018(2) .025(2) .009(2) C22 .067(2) .094(3) .074(2) -.018(2) .0129(19) .002(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 C2 . 1.364(4) ? O1 C9 . 1.389(4) ? O2 C2 . 1.213(4) ? C2 C3 . 1.449(5) ? C3 C4 . 1.372(4) ? C3 C21 . 1.426(5) ? C4 C10 . 1.443(4) ? C4 C11 . 1.459(4) ? C5 C6 . 1.364(4) ? C5 C10 . 1.407(4) ? C5 H5 . .9300 ? C6 C7 . 1.392(5) ? C6 C22 . 1.505(5) ? C7 C8 . 1.379(6) ? C7 H7 . .9300 ? C8 C9 . 1.367(5) ? C8 H8 . .9300 ? C9 C10 . 1.390(4) ? C11 C12 . 1.322(4) ? C11 H11 . .9300 ? C12 C18 . 1.460(4) ? C12 H12 . .9300 ? C13 C14 . 1.360(4) ? C13 C18 . 1.392(4) ? C13 H13 . .9300 ? C14 C15 . 1.401(4) ? C14 H14 . .9300 ? C15 O19 . 1.362(4) ? C15 C16 . 1.373(4) ? C16 C17 . 1.378(4) ? C16 H16 . .9300 ? C17 C18 . 1.403(4) ? C17 H17 . .9300 ? O19 C20 . 1.428(5) ? C20 H201 . .9600 ? C20 H202 . .9600 ? C20 H203 . .9600 ? C21 N21 . 1.150(5) ? C22 H221 . .9600 ? C22 H222 . .9600 ? C22 H223 . .9600 ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 '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' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 '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 C2 O1 C9 121.4(2) O2 C2 O1 117.5(3) O2 C2 C3 124.9(4) O1 C2 C3 117.6(3) C4 C3 C21 123.0(3) C4 C3 C2 122.5(3) C21 C3 C2 114.4(3) C3 C4 C10 117.7(3) C3 C4 C11 122.2(3) C10 C4 C11 120.1(2) C6 C5 C10 122.2(3) C6 C5 H5 118.9 C10 C5 H5 118.9 C5 C6 C7 118.6(3) C5 C6 C22 120.3(3) C7 C6 C22 121.2(3) C8 C7 C6 121.0(3) C8 C7 H7 119.5 C6 C7 H7 119.5 C9 C8 C7 119.3(3) C9 C8 H8 120.3 C7 C8 H8 120.3 C8 C9 O1 116.7(3) C8 C9 C10 121.9(3) O1 C9 C10 121.3(3) C9 C10 C5 117.0(3) C9 C10 C4 119.3(3) C5 C10 C4 123.7(3) C12 C11 C4 122.5(3) C12 C11 H11 118.7 C4 C11 H11 118.7 C11 C12 C18 127.6(3) C11 C12 H12 116.2 C18 C12 H12 116.2 C14 C13 C18 122.4(3) C14 C13 H13 118.8 C18 C13 H13 118.8 C13 C14 C15 119.3(3) C13 C14 H14 120.3 C15 C14 H14 120.3 O19 C15 C16 125.3(3) O19 C15 C14 114.8(3) C16 C15 C14 119.8(3) C15 C16 C17 120.2(3) C15 C16 H16 119.9 C17 C16 H16 119.9 C16 C17 C18 121.0(3) C16 C17 H17 119.5 C18 C17 H17 119.5 C13 C18 C17 117.2(3) C13 C18 C12 119.7(3) C17 C18 C12 123.1(3) C15 O19 C20 116.9(3) O19 C20 H201 109.5 O19 C20 H202 109.5 H201 C20 H202 109.5 O19 C20 H203 109.5 H201 C20 H203 109.5 H202 C20 H203 109.5 N21 C21 C3 178.1(4) C6 C22 H221 109.5 C6 C22 H222 109.5 H221 C22 H222 109.5 C6 C22 H223 109.5 H221 C22 H223 109.5 H222 C22 H223 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 _geom_hbond_publ_flag C12 H12 O2 3_655 .93 2.67 3.406(4) 137 yes C13 H13 O2 3_655 .93 2.55 3.365(4) 147 yes C22 H222 O19 4_764 .96 2.61 3.566(4) 173 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 C9 O1 C2 O2 -179.4(3) C9 O1 C2 C3 .2(5) O2 C2 C3 C4 -178.6(3) O1 C2 C3 C4 1.7(5) O2 C2 C3 C21 3.3(5) O1 C2 C3 C21 -176.3(3) C21 C3 C4 C10 175.0(3) C2 C3 C4 C10 -2.8(4) C21 C3 C4 C11 -5.1(5) C2 C3 C4 C11 177.1(3) C10 C5 C6 C7 1.4(5) C10 C5 C6 C22 -179.9(3) C5 C6 C7 C8 -.2(6) C22 C6 C7 C8 -179.0(3) C6 C7 C8 C9 -.6(6) C7 C8 C9 O1 -179.3(3) C7 C8 C9 C10 .4(5) C2 O1 C9 C8 178.8(3) C2 O1 C9 C10 -.9(5) C8 C9 C10 C5 .7(5) O1 C9 C10 C5 -179.6(2) C8 C9 C10 C4 -180.0(3) O1 C9 C10 C4 -.2(4) C6 C5 C10 C9 -1.6(4) C6 C5 C10 C4 179.1(3) C3 C4 C10 C9 2.0(4) C11 C4 C10 C9 -177.9(3) C3 C4 C10 C5 -178.6(3) C11 C4 C10 C5 1.5(4) C3 C4 C11 C12 -47.6(4) C10 C4 C11 C12 132.3(3) C4 C11 C12 C18 -178.6(3) C18 C13 C14 C15 1.0(5) C13 C14 C15 O19 179.7(3) C13 C14 C15 C16 -1.0(5) O19 C15 C16 C17 179.9(3) C14 C15 C16 C17 .8(5) C15 C16 C17 C18 -.4(5) C14 C13 C18 C17 -.6(4) C14 C13 C18 C12 179.0(3) C16 C17 C18 C13 .3(4) C16 C17 C18 C12 -179.3(3) C11 C12 C18 C13 169.6(3) C11 C12 C18 C17 -10.7(5) C16 C15 O19 C20 1.6(5) C14 C15 O19 C20 -179.2(3)