#------------------------------------------------------------------------------ #$Date: 2008-04-03 13:11:48 +0300 (Thu, 03 Apr 2008) $ #$Revision: 326 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2205420.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_2205420 loop_ _publ_author_name 'K. Ravikumar' 'B. Sridhar' 'P. Aparna' 'J. Madhusudana Rao' _publ_section_title ; A polymorph of bavachalcone ; _journal_issue 4 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o1020 _journal_page_last o1022 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C21 H22 O4' _chemical_formula_moiety 'C21 H22 O4' _chemical_formula_sum 'C21 H22 O4' _chemical_formula_weight 338.39 _chemical_name_systematic ; 1-[2-hydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop- 2-en-1-one ; _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 101.6390(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.5025(5) _cell_length_b 22.5080(15) _cell_length_c 11.1960(7) _cell_measurement_reflns_used 5568 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 27.04 _cell_measurement_theta_min 2.59 _cell_volume 1851.8(2) _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 0.999 _diffrn_measured_fraction_theta_max 0.968 _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_device_type '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 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 15814 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 28.00 _diffrn_reflns_theta_min 1.81 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.214 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Needle _exptl_crystal_F_000 720 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.258 _refine_diff_density_min -0.149 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 231 _refine_ls_number_reflns 4328 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0527 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0863P)^2^+0.1910P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1457 _refine_ls_wR_factor_ref 0.1584 _reflns_number_gt 3210 _reflns_number_total 4328 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bt6625.cif 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_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_ _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 O1 0.93913(17) 0.56235(4) 0.21775(10) 0.0721(3) Uani d . 1 O O2 0.80513(18) 0.63025(4) 0.04795(10) 0.0719(3) Uani d . 1 O H2A 0.8622 0.6201 0.1152 0.108 Uiso calc R 1 H O3 1.2333(2) 0.23790(5) 0.56933(11) 0.0921(5) Uani d . 1 O H3 1.2124 0.2090 0.5242 0.138 Uiso calc R 1 H O4 0.48216(16) 0.54349(5) -0.32069(10) 0.0719(3) Uani d . 1 O C1 1.0777(2) 0.34042(6) 0.31741(12) 0.0557(3) Uani d . 1 C H1 1.0414 0.3399 0.2329 0.067 Uiso calc R 1 H C2 1.1304(2) 0.28837(6) 0.37819(13) 0.0609(4) Uani d . 1 C H2 1.1310 0.2532 0.3347 0.073 Uiso calc R 1 H C3 1.1826(2) 0.28814(6) 0.50438(13) 0.0608(4) Uani d . 1 C C4 1.1857(2) 0.34084(7) 0.56738(13) 0.0668(4) Uani d . 1 C H4 1.2220 0.3412 0.6519 0.080 Uiso calc R 1 H C5 1.1356(2) 0.39271(6) 0.50595(13) 0.0607(4) Uani d . 1 C H5 1.1405 0.4280 0.5497 0.073 Uiso calc R 1 H C6 1.07762(18) 0.39404(6) 0.37976(12) 0.0502(3) Uani d . 1 C C7 1.0223(2) 0.45003(6) 0.31922(13) 0.0550(3) Uani d . 1 C H7 1.0503 0.4841 0.3661 0.066 Uiso calc R 1 H C8 0.9365(2) 0.45818(6) 0.20486(13) 0.0554(3) Uani d . 1 C H8 0.9048 0.4251 0.1552 0.066 Uiso calc R 1 H C9 0.8897(2) 0.51742(6) 0.15390(13) 0.0536(3) Uani d . 1 C C10 0.78545(19) 0.52406(5) 0.02972(12) 0.0494(3) Uani d . 1 C C11 0.7430(2) 0.58132(5) -0.01834(13) 0.0534(3) Uani d . 1 C C12 0.6389(2) 0.58928(6) -0.13391(13) 0.0556(3) Uani d . 1 C H12 0.6082 0.6274 -0.1632 0.067 Uiso calc R 1 H C13 0.58063(19) 0.54042(6) -0.20554(13) 0.0536(3) Uani d . 1 C C14 0.62374(19) 0.48215(6) -0.16250(13) 0.0537(3) Uani d . 1 C C15 0.72286(19) 0.47579(6) -0.04657(13) 0.0514(3) Uani d . 1 C H15 0.7502 0.4376 -0.0168 0.062 Uiso calc R 1 H C16 0.5641(3) 0.43009(6) -0.24531(16) 0.0748(5) Uani d . 1 C H16A 0.4398 0.4368 -0.2880 0.090 Uiso calc R 1 H H16B 0.6397 0.4284 -0.3060 0.090 Uiso calc R 1 H C17 0.5731(2) 0.37133(6) -0.18241(16) 0.0668(4) Uani d . 1 C H17 0.5227 0.3699 -0.1131 0.080 Uiso calc R 1 H C18 0.6432(2) 0.32150(7) -0.21259(15) 0.0681(4) Uani d . 1 C C19 0.6263(4) 0.26485(8) -0.1447(2) 0.1055(7) Uani d . 1 C H19A 0.5603 0.2724 -0.0812 0.158 Uiso calc R 1 H H19B 0.7455 0.2502 -0.1095 0.158 Uiso calc R 1 H H19C 0.5624 0.2358 -0.2001 0.158 Uiso calc R 1 H C20 0.7356(4) 0.31540(10) -0.3181(2) 0.1080(8) Uani d . 1 C H20A 0.7712 0.3539 -0.3416 0.162 Uiso calc R 1 H H20B 0.6537 0.2975 -0.3854 0.162 Uiso calc R 1 H H20C 0.8416 0.2908 -0.2951 0.162 Uiso calc R 1 H C21 0.4255(3) 0.60019(8) -0.37100(17) 0.0791(5) Uani d . 1 C H21A 0.5305 0.6233 -0.3777 0.119 Uiso calc R 1 H H21B 0.3581 0.6203 -0.3188 0.119 Uiso calc R 1 H H21C 0.3498 0.5951 -0.4504 0.119 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 0.1065(9) 0.0460(6) 0.0590(6) 0.0034(5) 0.0052(6) -0.0082(5) O2 0.1073(9) 0.0365(5) 0.0673(7) 0.0017(5) 0.0070(6) -0.0040(4) O3 0.1522(13) 0.0476(6) 0.0630(7) 0.0041(7) -0.0105(7) 0.0071(5) O4 0.0863(8) 0.0547(6) 0.0654(7) 0.0067(5) -0.0069(5) 0.0092(5) C1 0.0711(9) 0.0487(7) 0.0440(7) -0.0016(6) 0.0037(6) -0.0030(6) C2 0.0825(10) 0.0427(7) 0.0533(8) -0.0042(6) 0.0035(7) -0.0085(6) C3 0.0775(10) 0.0434(7) 0.0558(8) -0.0022(6) 0.0005(7) 0.0027(6) C4 0.0941(11) 0.0562(8) 0.0434(7) 0.0029(8) -0.0022(7) -0.0035(6) C5 0.0809(10) 0.0466(7) 0.0498(7) 0.0052(7) 0.0019(7) -0.0084(6) C6 0.0553(7) 0.0456(7) 0.0480(7) 0.0003(5) 0.0064(5) -0.0024(5) C7 0.0664(8) 0.0447(7) 0.0530(8) 0.0045(6) 0.0101(6) -0.0038(6) C8 0.0708(9) 0.0428(7) 0.0519(7) 0.0005(6) 0.0110(6) -0.0001(6) C9 0.0671(8) 0.0437(7) 0.0516(7) 0.0030(6) 0.0155(6) -0.0015(6) C10 0.0600(8) 0.0380(6) 0.0520(7) 0.0036(5) 0.0155(6) 0.0009(5) C11 0.0678(8) 0.0361(6) 0.0591(8) 0.0032(6) 0.0194(6) -0.0006(5) C12 0.0668(8) 0.0382(6) 0.0634(8) 0.0079(6) 0.0168(7) 0.0077(6) C13 0.0560(8) 0.0473(7) 0.0570(8) 0.0047(6) 0.0100(6) 0.0061(6) C14 0.0603(8) 0.0404(6) 0.0584(8) 0.0021(6) 0.0075(6) -0.0005(6) C15 0.0632(8) 0.0351(6) 0.0555(7) 0.0042(5) 0.0114(6) 0.0033(5) C16 0.0964(12) 0.0467(8) 0.0690(10) 0.0002(7) -0.0128(9) -0.0038(7) C17 0.0755(10) 0.0483(8) 0.0720(10) -0.0073(7) 0.0043(8) -0.0038(7) C18 0.0753(10) 0.0483(8) 0.0745(10) 0.0008(7) 0.0005(8) 0.0000(7) C19 0.1276(18) 0.0540(10) 0.1344(19) 0.0016(11) 0.0254(15) 0.0178(11) C20 0.148(2) 0.0847(14) 0.0940(15) 0.0314(13) 0.0309(14) 0.0016(12) C21 0.0805(11) 0.0665(10) 0.0821(11) 0.0058(8) -0.0036(9) 0.0267(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C9 1.2506(16) y O2 C11 1.3570(16) ? O2 H2A 0.8200 ? O3 C3 1.3568(17) y O3 H3 0.8200 ? O4 C13 1.3521(17) y O4 C21 1.4248(18) ? C1 C2 1.3723(19) ? C1 C6 1.3943(18) ? C1 H1 0.9300 ? C2 C3 1.388(2) ? C2 H2 0.9300 ? C3 C4 1.378(2) ? C4 C5 1.369(2) ? C4 H4 0.9300 ? C5 C6 1.3922(18) ? C5 H5 0.9300 ? C6 C7 1.4514(18) ? C7 C8 1.3246(19) ? C7 H7 0.9300 ? C8 C9 1.4649(18) ? C8 H8 0.9300 ? C9 C10 1.4588(19) ? C10 C15 1.4033(18) ? C10 C11 1.4081(17) ? C11 C12 1.382(2) ? C12 C13 1.379(2) ? C12 H12 0.9300 ? C13 C14 1.4121(18) ? C14 C15 1.3670(19) ? C14 C16 1.5053(19) y C15 H15 0.9300 ? C16 C17 1.493(2) ? C16 H16A 0.9700 ? C16 H16B 0.9700 ? C17 C18 1.312(2) y C17 H17 0.9300 ? C18 C20 1.492(3) ? C18 C19 1.503(2) ? C19 H19A 0.9600 ? C19 H19B 0.9600 ? C19 H19C 0.9600 ? C20 H20A 0.9600 ? C20 H20B 0.9600 ? C20 H20C 0.9600 ? C21 H21A 0.9600 ? C21 H21B 0.9600 ? C21 H21C 0.9600 ? 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 C11 O2 H2A 109.5 ? C3 O3 H3 109.5 ? C13 O4 C21 118.99(13) ? C2 C1 C6 121.32(12) ? C2 C1 H1 119.3 ? C6 C1 H1 119.3 ? C1 C2 C3 120.13(12) ? C1 C2 H2 119.9 ? C3 C2 H2 119.9 ? O3 C3 C4 117.98(13) ? O3 C3 C2 122.67(13) ? C4 C3 C2 119.34(13) ? C5 C4 C3 120.17(13) ? C5 C4 H4 119.9 ? C3 C4 H4 119.9 ? C4 C5 C6 121.75(13) ? C4 C5 H5 119.1 ? C6 C5 H5 119.1 ? C5 C6 C1 117.25(12) ? C5 C6 C7 119.61(12) y C1 C6 C7 123.14(12) ? C8 C7 C6 127.53(13) ? C8 C7 H7 116.2 ? C6 C7 H7 116.2 ? C7 C8 C9 122.28(13) ? C7 C8 H8 118.9 ? C9 C8 H8 118.9 ? O1 C9 C10 120.14(12) ? O1 C9 C8 119.55(13) ? C10 C9 C8 120.31(12) ? C15 C10 C11 117.00(13) ? C15 C10 C9 123.37(11) ? C11 C10 C9 119.63(12) y O2 C11 C12 118.29(12) ? O2 C11 C10 120.51(13) ? C12 C11 C10 121.20(12) ? C13 C12 C11 119.62(12) ? C13 C12 H12 120.2 ? C11 C12 H12 120.2 ? O4 C13 C12 124.18(12) ? O4 C13 C14 114.60(12) ? C12 C13 C14 121.21(13) ? C15 C14 C13 117.69(12) ? C15 C14 C16 122.71(12) y C13 C14 C16 119.58(13) ? C14 C15 C10 123.23(12) ? C14 C15 H15 118.4 ? C10 C15 H15 118.4 ? C17 C16 C14 114.80(14) y C17 C16 H16A 108.6 ? C14 C16 H16A 108.6 ? C17 C16 H16B 108.6 ? C14 C16 H16B 108.6 ? H16A C16 H16B 107.5 ? C18 C17 C16 128.19(18) y C18 C17 H17 115.9 ? C16 C17 H17 115.9 ? C17 C18 C20 123.87(17) ? C17 C18 C19 121.10(18) ? C20 C18 C19 114.97(17) ? C18 C19 H19A 109.5 ? C18 C19 H19B 109.5 ? H19A C19 H19B 109.5 ? C18 C19 H19C 109.5 ? H19A C19 H19C 109.5 ? H19B C19 H19C 109.5 ? C18 C20 H20A 109.5 ? C18 C20 H20B 109.5 ? H20A C20 H20B 109.5 ? C18 C20 H20C 109.5 ? H20A C20 H20C 109.5 ? H20B C20 H20C 109.5 ? O4 C21 H21A 109.5 ? O4 C21 H21B 109.5 ? H21A C21 H21B 109.5 ? O4 C21 H21C 109.5 ? H21A C21 H21C 109.5 ? H21B C21 H21C 109.5 ? 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 C6 C1 C2 C3 0.9(3) C1 C2 C3 O3 179.02(15) C1 C2 C3 C4 -1.7(3) O3 C3 C4 C5 -179.95(16) C2 C3 C4 C5 0.8(3) C3 C4 C5 C6 1.1(3) C4 C5 C6 C1 -1.9(2) C4 C5 C6 C7 178.70(14) C2 C1 C6 C5 0.9(2) C2 C1 C6 C7 -179.71(14) C5 C6 C7 C8 -167.96(15) C1 C6 C7 C8 12.7(2) C6 C7 C8 C9 -179.30(13) C7 C8 C9 O1 3.4(2) C7 C8 C9 C10 -176.27(13) O1 C9 C10 C15 -178.95(14) C8 C9 C10 C15 0.8(2) O1 C9 C10 C11 0.9(2) C8 C9 C10 C11 -179.41(13) C15 C10 C11 O2 -177.26(13) C9 C10 C11 O2 2.9(2) C15 C10 C11 C12 2.2(2) C9 C10 C11 C12 -177.59(12) O2 C11 C12 C13 177.13(13) C10 C11 C12 C13 -2.4(2) C21 O4 C13 C12 -3.3(2) C21 O4 C13 C14 177.59(13) C11 C12 C13 O4 -178.31(13) C11 C12 C13 C14 0.7(2) O4 C13 C14 C15 -179.87(12) C12 C13 C14 C15 1.0(2) O4 C13 C14 C16 1.6(2) C12 C13 C14 C16 -177.53(15) C13 C14 C15 C10 -1.1(2) C16 C14 C15 C10 177.37(15) C11 C10 C15 C14 -0.5(2) C9 C10 C15 C14 179.37(13) C15 C14 C16 C17 16.7(2) C13 C14 C16 C17 -164.79(15) C14 C16 C17 C18 -132.30(19) C16 C17 C18 C20 2.1(3) C16 C17 C18 C19 -174.69(17) 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 O2 H2A O1 . 0.82 1.75 2.488(2) 148 O3 H3 O2 2_745 0.82 1.94 2.743(2) 166 C17 H17 O2 3_665 0.93 2.70 3.470(2) 140