#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202197.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_2202197 loop_ _publ_author_name 'T. Ravishankar' 'K. Chinnakali' 'S. Nanjundan' 'S. Radhakrishnan' 'Anwar Usman' 'Hoong-Kun Fun' _publ_section_title ; 1-(4-Methacryloyloxyphenyl)-3-(3-bromophenyl)prop-2-en-1-one ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o138 _journal_page_last o140 _journal_paper_doi 10.1107/S1600536803000126 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C19 H15 Br O3' _chemical_formula_sum 'C19 H15 Br O3' _chemical_formula_weight 371.22 _chemical_name_systematic ; 1-(4-Methacryloyloxyphenyl)-3-(3-bromophenyl)prop-2-en-1-one ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.8096(2) _cell_length_b 5.6168(2) _cell_length_c 37.2120(10) _cell_measurement_reflns_used 3329 _cell_measurement_temperature 203(2) _cell_measurement_theta_max 28.32 _cell_measurement_theta_min 3.28 _cell_volume 1632.30(8) _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 PLATON (Spek, 1990) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 203(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type ; 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 0.129 _diffrn_reflns_av_sigmaI/netI 0.1626 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_limit_l_min -49 _diffrn_reflns_number 9099 _diffrn_reflns_theta_full 28.26 _diffrn_reflns_theta_max 28.26 _diffrn_reflns_theta_min 3.28 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.530 _exptl_absorpt_correction_T_max 0.906 _exptl_absorpt_correction_T_min 0.431 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_description slab _exptl_crystal_F_000 752 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.68 _refine_diff_density_min -1.04 _refine_ls_abs_structure_details '(Flack, 1983)' _refine_ls_abs_structure_Flack 0.02(2) _refine_ls_extinction_coef 0.0196(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXTL _refine_ls_goodness_of_fit_ref 0.93 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 3381 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.93 _refine_ls_R_factor_all 0.136 _refine_ls_R_factor_gt 0.069 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0757P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.142 _refine_ls_wR_factor_ref 0.169 _reflns_number_gt 1860 _reflns_number_total 3381 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6130.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2202197 _cod_database_fobs_code 2202197 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, 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 0.60774(10) 0.14355(15) 0.26916(3) 0.0420(3) Uani d . 1 . . Br O1 0.6432(8) 0.6434(11) 0.45790(16) 0.0367(16) Uani d . 1 . . O O2 0.2936(6) 0.5582(9) 0.61016(12) 0.0219(12) Uani d . 1 . . O O3 0.4186(10) 0.2211(14) 0.63066(17) 0.057(2) Uani d . 1 . . O C1 0.5657(9) 0.1984(14) 0.34480(19) 0.0200(17) Uani d . 1 . . C H1 0.6252 0.3400 0.3413 0.024 Uiso calc R 1 . . H C2 0.5305(9) 0.0506(15) 0.3154(2) 0.0230(18) Uani d . 1 . . C C3 0.4436(10) -0.1614(14) 0.3204(2) 0.0283(19) Uani d . 1 . . C H3 0.4191 -0.2585 0.3009 0.034 Uiso calc R 1 . . H C4 0.3929(10) -0.2295(15) 0.3547(2) 0.0271(18) Uani d . 1 . . C H4 0.3348 -0.3723 0.3581 0.033 Uiso calc R 1 . . H C5 0.4290(9) -0.0845(15) 0.3839(2) 0.0237(18) Uani d . 1 . . C H5 0.3975 -0.1335 0.4068 0.028 Uiso calc R 1 . . H C6 0.5122(9) 0.1353(13) 0.37940(19) 0.0191(16) Uani d . 1 . . C C7 0.5464(10) 0.3037(13) 0.4088(2) 0.0209(17) Uani d . 1 . . C H7 0.6102 0.4373 0.4026 0.025 Uiso calc R 1 . . H C8 0.4984(10) 0.2905(14) 0.4429(2) 0.0249(18) Uani d . 1 . . C H8 0.4358 0.1605 0.4511 0.030 Uiso calc R 1 . . H C9 0.5455(10) 0.4855(16) 0.4680(2) 0.0221(18) Uani d . 1 . . C C10 0.4756(9) 0.4913(13) 0.50563(18) 0.0150(15) Uani d . 1 . . C C11 0.3703(9) 0.3112(13) 0.5199(2) 0.0193(17) Uani d . 1 . . C H11 0.3383 0.1826 0.5056 0.023 Uiso calc R 1 . . H C12 0.3144(10) 0.3257(13) 0.5553(2) 0.0206(17) Uani d . 1 . . C H12 0.2487 0.2043 0.5652 0.025 Uiso calc R 1 . . H C13 0.3575(9) 0.5214(13) 0.5753(2) 0.0153(16) Uani d . 1 . . C C14 0.4597(10) 0.7053(15) 0.5618(2) 0.0225(18) Uani d . 1 . . C H14 0.4873 0.8362 0.5759 0.027 Uiso calc R 1 . . H C15 0.5186(10) 0.6881(13) 0.5269(2) 0.0203(17) Uani d . 1 . . C H15 0.5873 0.8079 0.5174 0.024 Uiso calc R 1 . . H C16 0.3358(10) 0.3949(16) 0.6364(2) 0.028(2) Uani d . 1 . . C C17 0.2640(10) 0.4738(16) 0.6715(2) 0.0279(19) Uani d . 1 . . C C18 0.3066(14) 0.3351(17) 0.7002(2) 0.048(3) Uani d . 1 . . C H18A 0.2683 0.3753 0.7231 0.057 Uiso calc R 1 . . H H18B 0.3740 0.2003 0.6970 0.057 Uiso calc R 1 . . H C19 0.1600(11) 0.6873(15) 0.6733(2) 0.034(2) Uani d . 1 . . C H19A 0.1347 0.7229 0.6980 0.051 Uiso calc R 1 . . H H19B 0.0552 0.6625 0.6604 0.051 Uiso calc R 1 . . H H19C 0.2214 0.8180 0.6628 0.051 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 0.0517(5) 0.0607(6) 0.0136(4) -0.0036(5) 0.0052(6) -0.0037(6) O1 0.047(4) 0.041(4) 0.021(3) -0.022(3) 0.010(3) -0.007(3) O2 0.033(3) 0.025(3) 0.008(3) 0.003(2) 0.002(2) 0.003(2) O3 0.089(5) 0.059(5) 0.022(4) 0.040(4) -0.001(4) 0.008(3) C1 0.025(4) 0.021(5) 0.014(4) 0.003(3) 0.000(3) -0.006(3) C2 0.020(4) 0.032(5) 0.017(4) 0.005(3) 0.003(3) -0.008(3) C3 0.029(4) 0.032(5) 0.023(4) 0.008(4) -0.004(3) -0.014(4) C4 0.027(4) 0.020(4) 0.035(5) -0.002(4) 0.001(4) -0.012(3) C5 0.019(4) 0.035(5) 0.017(4) 0.004(3) 0.003(3) 0.002(3) C6 0.017(4) 0.028(4) 0.012(4) 0.002(3) 0.000(3) -0.006(3) C7 0.022(4) 0.023(5) 0.018(4) -0.003(3) -0.004(3) -0.004(3) C8 0.027(4) 0.025(5) 0.023(4) -0.005(3) -0.001(3) -0.007(3) C9 0.019(4) 0.030(5) 0.017(4) -0.007(4) -0.004(4) 0.003(4) C10 0.016(4) 0.011(4) 0.017(4) -0.003(3) 0.001(3) -0.006(3) C11 0.020(4) 0.020(4) 0.018(4) 0.001(3) 0.003(3) -0.003(3) C12 0.021(4) 0.015(4) 0.025(4) -0.006(3) 0.004(3) 0.001(3) C13 0.019(4) 0.013(4) 0.015(4) 0.003(3) 0.001(3) 0.004(3) C14 0.029(4) 0.020(5) 0.018(4) 0.000(3) -0.005(3) -0.004(3) C15 0.022(4) 0.017(4) 0.022(4) -0.007(3) -0.004(3) 0.002(3) C16 0.025(4) 0.044(6) 0.015(4) -0.001(4) -0.004(3) 0.006(4) C17 0.033(5) 0.037(5) 0.014(4) -0.008(4) -0.002(3) 0.007(4) C18 0.084(7) 0.046(6) 0.013(4) 0.007(5) -0.003(5) -0.009(4) C19 0.044(5) 0.040(5) 0.017(4) 0.008(4) 0.010(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' Br Br -0.2901 2.4595 '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 C16 O2 C13 118.0(6) ? C6 C1 C2 120.7(7) ? C6 C1 H1 119.7 ? C2 C1 H1 119.7 ? C3 C2 C1 120.0(7) ? C3 C2 Br1 121.1(6) ? C1 C2 Br1 118.9(6) ? C2 C3 C4 120.1(7) ? C2 C3 H3 119.9 ? C4 C3 H3 119.9 ? C5 C4 C3 119.9(8) ? C5 C4 H4 120.0 ? C3 C4 H4 120.0 ? C4 C5 C6 121.1(8) ? C4 C5 H5 119.4 ? C6 C5 H5 119.4 ? C1 C6 C5 118.1(7) ? C1 C6 C7 117.8(7) ? C5 C6 C7 124.1(7) yes C8 C7 C6 128.7(7) yes C8 C7 H7 115.7 ? C6 C7 H7 115.7 ? C7 C8 C9 119.4(8) ? C7 C8 H8 120.3 ? C9 C8 H8 120.3 ? O1 C9 C8 119.7(8) ? O1 C9 C10 119.6(7) ? C8 C9 C10 120.7(7) ? C15 C10 C11 119.7(6) ? C15 C10 C9 117.1(6) yes C11 C10 C9 123.2(6) yes C12 C11 C10 119.9(7) ? C12 C11 H11 120.1 ? C10 C11 H11 120.1 ? C13 C12 C11 119.1(7) ? C13 C12 H12 120.5 ? C11 C12 H12 120.5 ? C12 C13 C14 122.4(7) yes C12 C13 O2 122.2(7) yes C14 C13 O2 115.3(6) yes C15 C14 C13 118.5(7) ? C15 C14 H14 120.7 ? C13 C14 H14 120.7 ? C14 C15 C10 120.4(7) ? C14 C15 H15 119.8 ? C10 C15 H15 119.8 ? O3 C16 O2 123.3(7) yes O3 C16 C17 127.2(7) yes O2 C16 C17 109.4(7) yes C18 C17 C19 124.8(8) yes C18 C17 C16 115.2(8) yes C19 C17 C16 119.9(7) ? C17 C18 H18A 120.0 ? C17 C18 H18B 120.0 ? H18A C18 H18B 120.0 ? C17 C19 H19A 109.5 ? C17 C19 H19B 109.5 ? H19A C19 H19B 109.5 ? C17 C19 H19C 109.5 ? H19A C19 H19C 109.5 ? H19B C19 H19C 109.5 ? 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 C2 . 1.896(8) ? O1 C9 . 1.228(10) ? O2 C16 . 1.379(9) ? O2 C13 . 1.404(9) ? O3 C16 . 1.190(10) ? C1 C6 . 1.399(10) ? C1 C2 . 1.401(10) ? C1 H1 . 0.93 ? C2 C3 . 1.383(11) ? C3 C4 . 1.389(12) ? C3 H3 . 0.93 ? C4 C5 . 1.386(11) ? C4 H4 . 0.93 ? C5 C6 . 1.405(10) ? C5 H5 . 0.93 ? C6 C7 . 1.470(10) ? C7 C8 . 1.326(11) ? C7 H7 . 0.93 ? C8 C9 . 1.485(11) ? C8 H8 . 0.93 ? C9 C10 . 1.505(10) ? C10 C15 . 1.400(10) ? C10 C11 . 1.407(10) ? C11 C12 . 1.389(11) ? C11 H11 . 0.93 ? C12 C13 . 1.371(11) ? C12 H12 . 0.93 ? C13 C14 . 1.399(12) ? C14 C15 . 1.381(10) ? C14 H14 . 0.93 ? C15 H15 . 0.93 ? C16 C17 . 1.489(11) ? C17 C18 . 1.365(12) ? C17 C19 . 1.450(11) ? C18 H18A . 0.93 ? C18 H18B . 0.93 ? C19 H19A . 0.96 ? C19 H19B . 0.96 ? C19 H19C . 0.96 ? 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 C7 H7 O1 1_555 0.93 2.38 2.748(10) 104 yes C15 H15 O1 1_555 0.93 2.44 2.757(10) 100 yes C1 H1 CgA 3_555 0.93 2.95 3.690(8) 138 yes C4 H4 CgA 3_445 0.93 2.87 3.541(8) 130 yes C12 H12 CgB 3_455 0.93 3.00 3.670(8) 130 yes C15 H15 CgB 3_565 0.93 2.90 3.582(8) 131 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 C6 C1 C2 C3 -0.7(11) ? C6 C1 C2 Br1 -179.5(5) ? C1 C2 C3 C4 -0.8(12) ? Br1 C2 C3 C4 178.0(6) ? C2 C3 C4 C5 0.2(12) ? C3 C4 C5 C6 1.9(11) ? C2 C1 C6 C5 2.6(11) ? C2 C1 C6 C7 -177.2(7) ? C4 C5 C6 C1 -3.2(10) ? C4 C5 C6 C7 176.6(7) ? C1 C6 C7 C8 175.1(8) yes C5 C6 C7 C8 -4.8(13) ? C6 C7 C8 C9 -179.0(7) yes C7 C8 C9 O1 -7.7(13) yes C7 C8 C9 C10 172.6(7) yes O1 C9 C10 C15 3.7(11) ? C8 C9 C10 C15 -176.5(7) yes O1 C9 C10 C11 -176.6(8) ? C8 C9 C10 C11 3.2(12) ? C15 C10 C11 C12 -2.1(11) ? C9 C10 C11 C12 178.2(7) ? C10 C11 C12 C13 2.6(11) ? C11 C12 C13 C14 -1.6(12) ? C11 C12 C13 O2 174.4(7) ? C16 O2 C13 C12 62.9(10) ? C16 O2 C13 C14 -120.8(7) ? C12 C13 C14 C15 0.1(12) ? O2 C13 C14 C15 -176.2(7) ? C13 C14 C15 C10 0.4(11) ? C11 C10 C15 C14 0.5(11) ? C9 C10 C15 C14 -179.7(7) ? C13 O2 C16 O3 -2.6(12) ? C13 O2 C16 C17 176.8(6) ? O3 C16 C17 C18 3.5(14) ? O2 C16 C17 C18 -175.8(7) ? O3 C16 C17 C19 -177.7(10) ? O2 C16 C17 C19 2.9(11) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30654694 2 PubChem 101749976