#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/25/2012507.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_2012507 loop_ _publ_author_name 'Ziyat, Hossni' 'Ait Itto, My Youssef' 'Ait Ali, Mustapha' 'Karim, Abdellah' 'Riahi, Abdelkhalek' 'Daran, Jean-Claude' _publ_section_title ; Stereochemistry of two new polyfunctionalized gem-dihalocyclopropanes ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o90 _journal_page_last o93 _journal_paper_doi 10.1107/S0108270101019680 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C11 H16 Br2 O3' _chemical_formula_structural 'C11 H16 Br2 O3' _chemical_formula_sum 'C11 H16 Br2 O3' _chemical_formula_weight 356.06 _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.4006(5) _cell_length_b 9.7511(10) _cell_length_c 18.0171(13) _cell_measurement_reflns_used 8000 _cell_measurement_temperature 180(2) _cell_measurement_theta_max 26.02 _cell_measurement_theta_min 2.3 _cell_volume 1300.19(19) _computing_cell_refinement 'IPDS software (Stoe, 1996)' _computing_data_collection 'IPDS software (Stoe, 1996)' _computing_data_reduction 'XRED (Stoe, 1.08, 1996)' _computing_molecular_graphics 'ORTEPIII( Burnett and Johnson,1996)' _computing_publication_material 'WINGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_structure_solution 'SIR97 (Altomare, et al.,1999)' _diffrn_measured_fraction_theta_full .925 _diffrn_measured_fraction_theta_max .925 _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method \f _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0737 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 9311 _diffrn_reflns_theta_full 26.06 _diffrn_reflns_theta_max 26.06 _diffrn_reflns_theta_min 2.26 _diffrn_standards_decay_% <0.1 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 6.225 _exptl_absorpt_correction_T_max .348 _exptl_absorpt_correction_T_min .162 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV, Blessing (1995)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.819 _exptl_crystal_density_method 'not measured' _exptl_crystal_description parallelepiped _exptl_crystal_F_000 704 _exptl_crystal_size_max .3 _exptl_crystal_size_mid .28 _exptl_crystal_size_min .18 _refine_diff_density_max .511 _refine_diff_density_min -.564 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -.03(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 148 _refine_ls_number_reflns 2376 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.089 _refine_ls_R_factor_all .0465 _refine_ls_R_factor_gt .0370 _refine_ls_shift/su_max .016 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0553P)^2^+0.1506P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .0869 _refine_ls_wR_factor_ref .0956 _reflns_number_gt 2070 _reflns_number_total 2376 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file jz1483.cif _cod_data_source_block 3 _cod_depositor_comments ; The following automatic conversions were performed: '_geom_bond_publ_flag' value 'YES' changed to 'yes' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (10 times). '_geom_bond_publ_flag' value 'NO' changed to 'no' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (6 times). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_geom_bond_publ_flag' value 'YES' changed to 'yes' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (10 times). '_geom_bond_publ_flag' value 'NO' changed to 'no' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (6 times). '_geom_angle_publ_flag' value 'NO' changed to 'no' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (9 times). '_geom_angle_publ_flag' value 'YES' changed to 'yes' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (16 times). '_geom_torsion_publ_flag' value 'YES' changed to 'yes' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (9 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2012507 _cod_database_fobs_code 2012507 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 Br1 .35714(9) .88593(6) .41179(3) .03788(17) Uani d . 1 . . Br Br2 .29276(10) .83970(7) .24107(3) .0465(2) Uani d . 1 . . Br O1 .7668(6) .4995(4) .4370(2) .0347(10) Uani d . 1 . . O O2 1.0233(7) .4611(4) .3769(3) .0399(10) Uani d . 1 . . O H2 1.0029 .3818 .3896 .060 Uiso calc R 1 . . H O3 .9632(7) 1.1939(4) .4001(2) .0405(11) Uani d . 1 . . O C1 .7587(8) .7810(5) .3802(3) .0270(12) Uani d . 1 . . C H1 .6928 .7664 .4267 .032 Uiso calc R 1 . . H C2 .6291(9) .7452(5) .3164(3) .0263(11) Uani d . 1 . . C C3 .4830(8) .6403(5) .3326(3) .0304(12) Uani d . 1 . . C H3A .4473 .5792 .2927 .036 Uiso calc R 1 . . H H3B .4799 .6000 .3818 .036 Uiso calc R 1 . . H C4 .4359(9) .7880(6) .3254(3) .0339(13) Uani d . 1 . . C C11 .8158(8) .9331(5) .3781(3) .0282(13) Uani d . 1 . . C H11A .9206 .9429 .3463 .034 Uiso calc R 1 . . H H11B .7185 .9871 .3569 .034 Uiso calc R 1 . . H C12 .8607(10) .9880(5) .4550(3) .0336(13) Uani d . 1 . . C H12A .7547 .9781 .4862 .040 Uiso calc R 1 . . H H12B .9555 .9315 .4761 .040 Uiso calc R 1 . . H C13 .9207(8) 1.1353(5) .4574(3) .0316(13) Uani d . 1 . . C C14 .9257(10) 1.2040(6) .5312(3) .0388(15) Uani d . 1 . . C H14A .9340 1.3014 .5245 .058 Uiso calc R 1 . . H H14B 1.0289 1.1722 .5586 .058 Uiso calc R 1 . . H H14C .8175 1.1825 .5582 .058 Uiso calc R 1 . . H C16 .9263(9) .6900(5) .3825(3) .0321(13) Uani d . 1 . . C H16A .9850 .6942 .3344 .039 Uiso calc R 1 . . H H16B 1.0096 .7276 .4187 .039 Uiso calc R 1 . . H C17 .8928(8) .5417(5) .4014(3) .0293(13) Uani d . 1 . . C C21 .7122(10) .7487(6) .2392(3) .0428(15) Uani d . 1 . . C H21A .8116 .6856 .2370 .064 Uiso calc R 1 . . H H21B .7547 .8397 .2288 .064 Uiso calc R 1 . . H H21C .6227 .7231 .2032 .064 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 .0343(3) .0354(3) .0439(3) .0003(2) .0014(3) -.0071(2) Br2 .0482(4) .0462(4) .0450(4) -.0071(3) -.0144(3) .0133(3) O1 .038(3) .0238(19) .042(2) -.0044(17) .0003(18) .0040(15) O2 .041(3) .0186(19) .061(3) .0012(18) .008(2) .0009(17) O3 .061(3) .021(2) .039(2) -.0048(18) .004(2) .0004(15) C1 .031(4) .016(2) .034(3) -.002(2) .000(2) .0023(18) C2 .033(3) .018(2) .028(3) .000(2) .001(2) .0009(17) C3 .035(4) .021(3) .035(3) -.007(2) -.002(2) .000(2) C4 .040(4) .025(3) .036(3) -.008(2) -.003(2) -.002(2) C11 .032(4) .018(2) .035(3) -.003(2) -.002(2) .0010(18) C12 .041(4) .024(3) .035(3) .001(3) .000(3) .001(2) C13 .033(4) .024(3) .038(3) .002(2) .001(2) .000(2) C14 .040(4) .033(3) .043(3) .002(3) -.005(3) -.008(2) C16 .038(4) .019(3) .040(3) .000(2) .003(2) .001(2) C17 .033(4) .020(3) .035(3) -.001(2) -.005(2) .001(2) C21 .054(4) .041(3) .033(3) .001(3) .008(3) .002(2) 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 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .006 '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 C17 O2 H2 109.5 ? C16 C1 C2 113.3(4) no C16 C1 C11 109.7(5) no C2 C1 C11 111.8(4) no C16 C1 H1 107.3 ? C2 C1 H1 107.3 ? C11 C1 H1 107.3 ? C4 C2 C3 59.1(4) yes C4 C2 C21 118.6(5) yes C3 C2 C21 118.7(5) yes C4 C2 C1 116.8(5) yes C3 C2 C1 117.0(4) yes C21 C2 C1 115.3(6) yes C4 C3 C2 59.9(4) yes C4 C3 H3A 117.8 ? C2 C3 H3A 117.8 ? C4 C3 H3B 117.8 ? C2 C3 H3B 117.8 ? H3A C3 H3B 114.9 ? C3 C4 C2 61.0(4) yes C3 C4 Br1 118.9(4) yes C2 C4 Br1 121.1(4) yes C3 C4 Br2 116.9(4) yes C2 C4 Br2 121.0(4) yes Br1 C4 Br2 110.1(3) yes C12 C11 C1 112.1(4) no C12 C11 H11A 109.2 ? C1 C11 H11A 109.2 ? C12 C11 H11B 109.2 ? C1 C11 H11B 109.2 ? H11A C11 H11B 107.9 ? C13 C12 C11 115.3(4) no C13 C12 H12A 108.5 ? C11 C12 H12A 108.5 ? C13 C12 H12B 108.5 ? C11 C12 H12B 108.5 ? H12A C12 H12B 107.5 ? O3 C13 C14 122.6(5) no O3 C13 C12 119.9(5) no C14 C13 C12 117.5(5) no C13 C14 H14A 109.5 ? C13 C14 H14B 109.5 ? H14A C14 H14B 109.5 ? C13 C14 H14C 109.5 ? H14A C14 H14C 109.5 ? H14B C14 H14C 109.5 ? C17 C16 C1 115.5(5) no C17 C16 H16A 108.4 ? C1 C16 H16A 108.4 ? C17 C16 H16B 108.4 ? C1 C16 H16B 108.4 ? H16A C16 H16B 107.5 ? O1 C17 O2 122.7(5) yes O1 C17 C16 125.1(5) yes O2 C17 C16 112.1(5) yes C2 C21 H21A 109.5 ? C2 C21 H21B 109.5 ? H21A C21 H21B 109.5 ? C2 C21 H21C 109.5 ? H21A C21 H21C 109.5 ? H21B C21 H21C 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 C4 . 1.917(6) yes Br2 C4 . 1.919(6) yes O1 C17 . 1.204(7) yes O2 C17 . 1.321(7) yes O2 H2 . .8200 ? O3 C13 . 1.220(7) yes C1 C16 . 1.525(8) no C1 C2 . 1.537(8) yes C1 C11 . 1.543(7) no C1 H1 . .9800 ? C2 C4 . 1.499(9) yes C2 C3 . 1.517(8) yes C2 C21 . 1.520(8) yes C3 C4 . 1.488(8) yes C3 H3A . .9700 ? C3 H3B . .9700 ? C11 C12 . 1.521(7) no C11 H11A . .9700 ? C11 H11B . .9700 ? C12 C13 . 1.504(8) no C12 H12A . .9700 ? C12 H12B . .9700 ? C13 C14 . 1.490(8) no C14 H14A . .9600 ? C14 H14B . .9600 ? C14 H14C . .9600 ? C16 C17 . 1.506(7) no C16 H16A . .9700 ? C16 H16B . .9700 ? C21 H21A . .9600 ? C21 H21B . .9600 ? C21 H21C . .9600 ? 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 H2 O3 1_545 .82 1.87 2.676(5) 169.5 C3 H3B O1 1_555 .97 2.54 3.136(7) 119.6 C1 H1 Br1 1_555 .98 2.76 3.194(6) 107.6 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 C16 C1 C2 C4 157.4(5) ? C11 C1 C2 C4 -78.1(6) ? C16 C1 C2 C3 90.2(6) ? C11 C1 C2 C3 -145.2(5) ? C16 C1 C2 C21 -56.4(6) ? C11 C1 C2 C21 68.1(6) ? C21 C2 C3 C4 -108.0(6) ? C1 C2 C3 C4 106.6(5) ? C2 C3 C4 Br1 -111.7(5) ? C2 C3 C4 Br2 112.2(5) ? C21 C2 C4 C3 108.1(5) ? C1 C2 C4 C3 -106.9(5) ? C3 C2 C4 Br1 108.1(5) ? C21 C2 C4 Br1 -143.8(5) ? C1 C2 C4 Br1 1.2(6) ? C3 C2 C4 Br2 -105.8(5) ? C21 C2 C4 Br2 2.3(7) ? C1 C2 C4 Br2 147.4(4) ? C16 C1 C11 C12 -81.8(6) yes C2 C1 C11 C12 151.7(5) yes C1 C11 C12 C13 179.0(6) yes C11 C12 C13 O3 -13.8(9) yes C11 C12 C13 C14 166.3(6) yes C2 C1 C16 C17 -67.1(6) yes C11 C1 C16 C17 167.2(4) yes C1 C16 C17 O1 -25.8(8) yes C1 C16 C17 O2 157.0(5) yes