#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/15/2101561.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_2101561 loop_ _publ_author_name 'Antoli\'c, A.' 'Koji\'c-Prodi\'c, B.' 'Tomi\'c, S.' 'Nigovi\'c, B.' 'Magnus, V.' 'Cohen, J. D.' _publ_section_title ; Structural studies on monofluorinated derivatives of the phytohormone indole-3-acetic acid (auxin) ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 651 _journal_page_last 661 _journal_paper_doi 10.1107/S0108768195016302 _journal_volume 52 _journal_year 1996 _chemical_formula_sum 'C10 H8 F N O2' _chemical_formula_weight 193.18 _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_type_scat_source 'SHELX76 (Sheldrick, 1976)' _cell_angle_alpha 90.0 _cell_angle_beta 103.88(6) _cell_angle_gamma 90.0 _cell_formula_units_Z 8 _cell_length_a 17.294(5) _cell_length_b 13.875(4) _cell_length_c 7.442(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 295 _cell_measurement_theta_max 15 _cell_measurement_theta_min 6 _cell_volume 1733.6(13) _diffrn_measurement_device 'Enraf-Nonius CAD4' _diffrn_measurement_method \w-\q _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 2566 _diffrn_reflns_theta_max 25 _diffrn_standards_decay_% <1 _diffrn_standards_interval_count 100 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.11 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.480 _exptl_crystal_description prismatic _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.17 _refine_diff_density_min -0.24 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.13 _refine_ls_hydrogen_treatment refall _refine_ls_number_parameters 159 _refine_ls_number_reflns 823 _refine_ls_R_factor_obs 0.043 _refine_ls_shift/esd_max -0.007 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = k/[\s^2^(F~o~) + gF~o~^2^] where g = 0.000528' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.044 _reflns_number_observed 823 _reflns_number_total 1293 _reflns_observed_criterion I>3\s(I) _[local]_cod_data_source_file se0185.cif _[local]_cod_data_source_block se0185a _[local]_cod_chemical_formula_sum_orig 'C10 H8 F1 N1 O2' _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = k/[\s^2^(F~o~) + gF~o~^2^] where g = 0.000528' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = k/[\s^2^(F~o~) + gF~o~^2^] where g = 0.000528'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1734.0(10) _cod_database_code 2101561 loop_ _symmetry_equiv_pos_as_xyz x,y,z x,-y,1/2+z -x,-y,-z -x,y,1/2-z 1/2+x,1/2+y,z 1/2+x,1/2-y,1/2+z 1/2-x,1/2-y,-z 1/2-x,1/2+y,1/2-z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv F .24110(10) .0038(2) .9763(3) .0672(8) O1 .0858(2) .1096(2) .4472(3) .0465(9) O2 .07850(10) -.0072(2) .6455(3) .0471(9) N1 .2886(2) .2942(3) .7258(5) .0570(10) C2 .2088(3) .2797(3) .6967(5) .0500(10) C3 .1936(2) .1941(2) .7675(4) .0420(10) C4 .2962(2) .0676(3) .9441(5) .0500(10) C5 .3747(3) .0487(4) 1.0108(7) .065(2) C6 .4311(3) .1141(4) .9768(7) .073(2) C7 .4092(3) .1978(4) .8807(6) .064(2) C8 .1125(2) .1536(3) .7613(5) .0460(10) C9 .0904(2) .0763(3) .6159(4) .0380(10) C31 .2693(2) .1512(3) .8471(4) .0410(10) C71 .3283(2) .2158(3) .8162(5) .050(2) H1 .309(3) .340(4) .683(7) .09(2) H2 .173(2) .330(2) .630(4) .039(9) H5 .390(3) -.009(3) 1.073(6) .080(10) H6 .482(3) .100(3) 1.007(6) .080(10) H7 .446(2) .242(3) .855(5) .080(10) H11 .077(2) .066(3) .366(6) .060(10) H81 .111(2) .129(2) .884(5) .050(10) H82 .070(3) .206(3) .729(6) .090(10) 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 C2 N1 C71 109.3(4) yes N1 C2 C3 110.7(4) yes C2 C3 C8 125.8(4) yes C2 C3 C31 106.4(4) yes C31 C3 C8 127.8(3) yes C3 C31 C4 136.3(3) yes C3 C31 C71 107.0(3) yes C4 C31 C71 116.7(3) yes C31 C4 C5 122.3(4) yes C4 C5 C6 119.3(5) yes C5 C6 C7 121.8(5) yes C6 C7 C71 117.6(5) yes C31 C71 C7 122.3(4) yes N1 C71 C7 131.0(4) yes N1 C71 C31 106.6(3) yes C3 C8 C9 111.3(3) yes C8 C9 O1 112.4(3) yes C8 C9 O2 125.3(3) yes O1 C9 O2 122.3(3) yes C31 C4 F 118.3(3) yes C5 C4 F 119.4(4) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 1.360(6) yes N1 C71 1.373(6) yes C2 C3 1.350(5) yes C3 C31 1.431(5) yes C4 C31 1.386(6) yes C4 C5 1.355(6) yes C5 C6 1.399(8) yes C6 C7 1.369(8) yes C7 C71 1.389(6) yes C31 C71 1.418(5) yes C3 C8 1.501(5) yes C8 C9 1.506(5) yes O1 C9 1.322(4) yes O2 C9 1.206(5) yes F C4 1.363(4) yes