#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/24/2012433.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_2012433 loop_ _publ_author_name 'Low, John N.' 'Cobo, Justo' 'Nogueras, Manuel' 'S\'anchez, Adolfo' 'Albornoz, Andrea' 'Abonia, Rodrigo' _publ_section_title ;A comparison of the supramolecular structures of 1-(6-amino-1,3-benzodioxol-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one and 1-(6-amino-1,3-benzodioxol-5-yl)-3-[4-(N,N-dimethylamino)phenyl]prop-2-en-1-one ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o42 _journal_page_last o45 _journal_paper_doi 10.1107/S0108270101018297 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C19 H19 N O6' _chemical_formula_sum 'C19 H19 N O6' _chemical_formula_weight 357.35 _chemical_melting_point 464 _chemical_name_systematic ; 1-(6-amino-1,3-benzodioxol-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 100.7020(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 23.5477(4) _cell_length_b 4.96050(10) _cell_length_c 14.2556(8) _cell_measurement_reflns_used 3622 _cell_measurement_temperature 150.0(10) _cell_measurement_theta_max 27.49 _cell_measurement_theta_min 3.11 _cell_volume 1636.21(10) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and PLATON (Spek, 2000)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150.0(10) _diffrn_measured_fraction_theta_full .981 _diffrn_measured_fraction_theta_max .959 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .048 _diffrn_reflns_av_sigmaI/netI .049 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 11152 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 3.11 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu .109 _exptl_absorpt_correction_T_max .989 _exptl_absorpt_correction_T_min .958 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.451 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 752 _exptl_crystal_size_max .4 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .1 _refine_diff_density_max .259 _refine_diff_density_min -.322 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 238 _refine_ls_number_reflns 3622 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.030 _refine_ls_R_factor_all .061 _refine_ls_R_factor_gt .044 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0675P)^2^+0.3552P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .108 _refine_ls_wR_factor_ref .124 _reflns_number_gt 2832 _reflns_number_total 3622 _reflns_threshold_expression I>2\s(I) _cod_data_source_file gd1178.cif _cod_data_source_block I _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_sg_symbol_H-M 'P 21/c' _cod_database_code 2012433 _cod_database_fobs_code 2012433 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 .16792(4) .9086(2) .04794(8) .0228(3) Uani d . 1 . . O C2 .12417(6) 1.0264(3) -.02328(11) .0216(3) Uani d . 1 . . C O3 .06873(4) .9492(2) -.00242(8) .0228(3) Uani d . 1 . . O C3a .07999(6) .7506(3) .06504(10) .0180(3) Uani d . 1 . . C C4 .04112(6) .5963(3) .10051(10) .0180(3) Uani d . 1 . . C C5 .06256(6) .3950(3) .16848(10) .0163(3) Uani d . 1 . . C N5 .02326(5) .2365(2) .20091(9) .0203(3) Uani d . 1 . . N C6 .12324(6) .3693(3) .20219(10) .0160(3) Uani d . 1 . . C C7 .16178(6) .5382(3) .16234(10) .0183(3) Uani d . 1 . . C C7a .13948(6) .7212(3) .09496(11) .0171(3) Uani d . 1 . . C C8 .14568(6) .1787(3) .27912(10) .0169(3) Uani d . 1 . . C O8 .11443(4) .0101(2) .30938(7) .0210(3) Uani d . 1 . . O C9 .20706(6) .2028(3) .32790(11) .0195(3) Uani d . 1 . . C C10 .22878(6) .0449(3) .40162(11) .0188(3) Uani d . 1 . . C C11 .28618(6) .0587(3) .46207(10) .0179(3) Uani d . 1 . . C C12 .32891(6) .2392(3) .44517(10) .0180(3) Uani d . 1 . . C C13 .38233(6) .2436(3) .50627(11) .0180(3) Uani d . 1 . . C O13 .42754(4) .4040(2) .49442(8) .0219(3) Uani d . 1 . . O C131 .42037(7) .5680(3) .41009(12) .0243(4) Uani d . 1 . . C C14 .39292(6) .0760(3) .58688(11) .0185(3) Uani d . 1 . . C O14 .44395(4) .1016(2) .65090(7) .0227(3) Uani d . 1 . . O C141 .48413(7) -.1152(3) .64751(12) .0252(4) Uani d . 1 . . C C15 .35021(7) -.1042(3) .60318(10) .0192(3) Uani d . 1 . . C O15 .36428(5) -.2597(2) .68360(8) .0255(3) Uani d . 1 . . O C151 .32121(7) -.4413(3) .70400(12) .0270(4) Uani d . 1 . . C C16 .29745(6) -.1155(3) .54069(10) .0187(3) Uani d . 1 . . C H2A .1280 .9611 -.0874 .026 Uiso calc R 1 . . H H2B .1280 1.2252 -.0222 .026 Uiso calc R 1 . . H H4 .0007 .6227 .0803 .022 Uiso calc R 1 . . H H5A .0356 .0908 .2337 .024 Uiso d R 1 . . H H5B -.0121 .2377 .1673 .024 Uiso d R 1 . . H H7 .2024 .5225 .1828 .022 Uiso calc R 1 . . H H9 .2312 .3330 .3062 .023 Uiso calc R 1 . . H H10 .2040 -.0932 .4167 .023 Uiso calc R 1 . . H H12 .3214 .3582 .3921 .022 Uiso calc R 1 . . H H13A .4094 .4538 .3535 .036 Uiso calc R 1 . . H H13B .4568 .6602 .4071 .036 Uiso calc R 1 . . H H13C .3900 .7020 .4121 .036 Uiso calc R 1 . . H H14A .4655 -.2873 .6568 .038 Uiso calc R 1 . . H H14B .5181 -.0905 .6981 .038 Uiso calc R 1 . . H H14C .4962 -.1154 .5853 .038 Uiso calc R 1 . . H H15A .2877 -.3387 .7159 .041 Uiso calc R 1 . . H H15B .3370 -.5480 .7607 .041 Uiso calc R 1 . . H H15C .3093 -.5620 .6495 .041 Uiso calc R 1 . . H H16 .2689 -.2416 .5513 .022 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 .0178(5) .0245(6) .0260(6) .0017(4) .0043(5) .0090(4) C2 .0208(8) .0234(8) .0200(8) .0017(6) .0028(6) .0049(6) O3 .0191(6) .0259(6) .0228(6) .0044(4) .0026(4) .0079(4) C3a .0196(8) .0185(7) .0150(7) .0039(6) .0009(6) -.0007(5) C4 .0136(7) .0203(7) .0188(8) .0026(5) -.0002(6) -.0022(6) C5 .0148(7) .0174(7) .0166(7) -.0004(5) .0023(6) -.0035(5) N5 .0147(6) .0198(6) .0258(7) -.0010(5) .0019(5) .0019(5) C6 .0165(7) .0142(7) .0168(7) .0018(5) .0018(6) -.0018(5) C7 .0129(7) .0218(7) .0195(8) .0019(6) .0012(6) -.0013(6) C7a .0164(7) .0175(7) .0180(8) -.0007(5) .0048(6) -.0005(5) C8 .0172(7) .0168(7) .0168(7) .0012(5) .0036(6) -.0029(5) O8 .0198(5) .0194(5) .0230(6) -.0021(4) .0021(4) .0026(4) C9 .0162(7) .0220(7) .0202(8) -.0009(6) .0028(6) .0022(6) C10 .0170(7) .0193(7) .0199(8) -.0003(6) .0026(6) -.0007(6) C11 .0163(7) .0209(7) .0164(8) .0031(6) .0026(6) -.0012(6) C12 .0180(7) .0190(7) .0163(8) .0028(6) .0016(6) .0004(6) C13 .0179(7) .0159(7) .0203(8) .0004(5) .0035(6) -.0027(6) O13 .0187(6) .0223(6) .0233(6) -.0044(4) -.0001(4) .0025(4) C131 .0238(8) .0217(8) .0272(9) -.0038(6) .0043(7) .0048(6) C14 .0159(7) .0203(7) .0176(8) .0019(6) -.0013(6) -.0034(6) O14 .0197(6) .0223(6) .0223(6) .0027(4) -.0059(4) -.0029(4) C141 .0187(8) .0256(8) .0284(9) .0033(6) -.0026(7) .0016(6) C15 .0217(8) .0188(7) .0167(8) .0040(6) .0027(6) .0009(6) O15 .0245(6) .0297(6) .0207(6) -.0004(5) -.0005(5) .0095(4) C151 .0289(9) .0262(8) .0267(9) .0020(7) .0070(7) .0085(6) C16 .0180(7) .0171(7) .0210(8) -.0001(5) .0036(6) .0003(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 '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 .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 _geom_angle_publ_flag C7a O1 C2 105.54(11) no O1 C2 O3 107.76(11) no O1 C2 H2A 110.2 no O3 C2 H2A 110.2 no O1 C2 H2B 110.2 no O3 C2 H2B 110.2 no H2A C2 H2B 108.5 no C3a O3 C2 105.75(11) no C4 C3a O3 127.62(13) no C4 C3a C7a 122.31(13) no O3 C3a C7a 110.06(12) no C3a C4 C5 118.13(13) no C3a C4 H4 120.9 no C5 C4 H4 120.9 no N5 C5 C4 117.48(13) no N5 C5 C6 122.44(13) no C4 C5 C6 120.06(13) no C5 N5 H5A 118.5 no C5 N5 H5B 116.5 no H5A N5 H5B 118.7 no C5 C6 C7 118.96(13) no C5 C6 C8 120.53(13) no C7 C6 C8 120.47(13) no C7a C7 C6 118.94(13) no C7a C7 H7 120.5 no C6 C7 H7 120.5 no C7 C7a O1 129.24(13) no C7 C7a C3a 121.48(13) no O1 C7a C3a 109.24(12) no O8 C8 C6 122.52(13) no O8 C8 C9 118.57(13) no C6 C8 C9 118.71(12) no C10 C9 C8 121.19(13) no C10 C9 H9 119.4 no C8 C9 H9 119.4 no C9 C10 C11 127.83(14) no C9 C10 H10 116.1 no C11 C10 H10 116.1 no C12 C11 C16 119.75(13) no C12 C11 C10 122.89(13) no C16 C11 C10 117.35(13) no C13 C12 C11 119.83(13) no C13 C12 H12 120.1 no C11 C12 H12 120.1 no O13 C13 C12 124.57(13) no O13 C13 C14 115.02(13) no C12 C13 C14 120.41(13) no C13 O13 C131 117.45(11) no O13 C131 H13A 109.5 no O13 C131 H13B 109.5 no H13A C131 H13B 109.5 no O13 C131 H13C 109.5 no H13A C131 H13C 109.5 no H13B C131 H13C 109.5 no O14 C14 C15 121.12(13) no O14 C14 C13 119.35(13) no C15 C14 C13 119.44(13) no C14 O14 C141 114.08(11) no O14 C141 H14A 109.5 no O14 C141 H14B 109.5 no H14A C141 H14B 109.5 no O14 C141 H14C 109.5 no H14A C141 H14C 109.5 no H14B C141 H14C 109.5 no O15 C15 C16 124.23(13) no O15 C15 C14 115.44(13) no C16 C15 C14 120.32(13) no C15 O15 C151 117.08(12) no O15 C151 H15A 109.5 no O15 C151 H15B 109.5 no H15A C151 H15B 109.5 no O15 C151 H15C 109.5 no H15A C151 H15C 109.5 no H15B C151 H15C 109.5 no C15 C16 C11 120.16(13) no C15 C16 H16 119.9 no C11 C16 H16 119.9 no 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 C7a . 1.3887(17) no O1 C2 . 1.4301(19) no C2 O3 . 1.4436(18) no C2 H2A . .9900 no C2 H2B . .9900 no O3 C3a . 1.3677(17) no C3a C4 . 1.361(2) no C3a C7a . 1.394(2) no C4 C5 . 1.417(2) no C4 H4 . .9500 no C5 N5 . 1.3594(18) no C5 C6 . 1.426(2) no N5 H5A . .8801 no N5 H5B . .8800 no C6 C7 . 1.428(2) no C6 C8 . 1.470(2) no C7 C7a . 1.355(2) no C7 H7 . .9500 no C8 O8 . 1.2431(17) no C8 C9 . 1.488(2) no C9 C10 . 1.334(2) no C9 H9 . .9500 no C10 C11 . 1.463(2) no C10 H10 . .9500 no C11 C12 . 1.401(2) no C11 C16 . 1.401(2) no C12 C13 . 1.391(2) no C12 H12 . .9500 no C13 O13 . 1.3646(17) no C13 C14 . 1.403(2) no O13 C131 . 1.4352(18) no C131 H13A . .9800 no C131 H13B . .9800 no C131 H13C . .9800 no C14 O14 . 1.3732(18) no C14 C15 . 1.397(2) no O14 C141 . 1.4392(18) no C141 H14A . .9800 no C141 H14B . .9800 no C141 H14C . .9800 no C15 O15 . 1.3704(18) no C15 C16 . 1.389(2) no O15 C151 . 1.4262(19) no C151 H15A . .9800 no C151 H15B . .9800 no C151 H15C . .9800 no C16 H16 . .9500 no 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 N5 H5A O8 . .88 2.01 2.651(2) 129 y C16 H16 O1 4_555 .95 2.51 3.398(2) 155 y 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 C7a O1 C2 O3 12.88(15) no O1 C2 O3 C3a -12.08(15) no C2 O3 C3a C4 -173.10(14) no C2 O3 C3a C7a 6.61(15) no O3 C3a C4 C5 178.10(13) no C7a C3a C4 C5 -1.6(2) no C3a C4 C5 N5 -177.85(12) no C3a C4 C5 C6 3.8(2) no N5 C5 C6 C7 178.10(13) no C4 C5 C6 C7 -3.6(2) no N5 C5 C6 C8 -4.0(2) no C4 C5 C6 C8 174.26(13) no C5 C6 C7 C7a 1.2(2) no C8 C6 C7 C7a -176.67(13) no C6 C7 C7a O1 178.55(13) no C6 C7 C7a C3a 1.0(2) no C2 O1 C7a C7 173.31(15) no C2 O1 C7a C3a -8.92(15) no C4 C3a C7a C7 -.8(2) no O3 C3a C7a C7 179.42(13) no C4 C3a C7a O1 -178.82(13) no O3 C3a C7a O1 1.45(16) no C5 C6 C8 O8 9.4(2) no C7 C6 C8 O8 -172.82(13) no C5 C6 C8 C9 -165.62(13) no C7 C6 C8 C9 12.2(2) no O8 C8 C9 C10 1.1(2) no C6 C8 C9 C10 176.25(13) no C8 C9 C10 C11 -174.20(13) no C9 C10 C11 C12 -4.3(2) no C9 C10 C11 C16 174.68(15) no C16 C11 C12 C13 .3(2) no C10 C11 C12 C13 179.21(13) no C11 C12 C13 O13 177.52(13) no C11 C12 C13 C14 -2.5(2) no C12 C13 O13 C131 -3.7(2) no C14 C13 O13 C131 176.36(12) no O13 C13 C14 O14 5.97(19) no C12 C13 C14 O14 -173.98(13) no O13 C13 C14 C15 -177.30(12) no C12 C13 C14 C15 2.7(2) no C15 C14 O14 C141 76.27(17) no C13 C14 O14 C141 -107.06(15) no O14 C14 C15 O15 -3.3(2) no C13 C14 C15 O15 -179.96(12) no O14 C14 C15 C16 175.99(13) no C13 C14 C15 C16 -.7(2) no C16 C15 O15 C151 -.8(2) no C14 C15 O15 C151 178.41(12) no O15 C15 C16 C11 177.63(13) no C14 C15 C16 C11 -1.6(2) no C12 C11 C16 C15 1.8(2) no C10 C11 C16 C15 -177.21(13) no