data_2000647 _journal_name_full 'Acta Cryst.' _journal_year 1992 _journal_volume C48 _journal_page_first 1722 _journal_page_last 1727 _publ_section_title ; Enantiomerically Pure \a-Haloketals: Structure and Conformation of (2'S,4R,5R)- Dimethyl 2'-halo-1',2',3',4'-tetrahydro- spiro[1,3-dioxolane-2,1'-naphthalene]-4,5- dicarboxylates (Halo = Cl, Br, I) ; loop_ _publ_author_name 'Sandra Ianelli' 'Mario Nardelli *' 'Claudio Giordano' 'Laura Coppi' 'Angelo Restelli' _chemical_name_systematic ; 2'-S-Bromo-3',4'-dihydro-spiro[1,3-dioxolane-2,1'- (2'H)-naphthalene]-4,5-R,R-dicarboxylic Acid Dimethyl Ester ; _chemical_formula_moiety ' C16 H17 Br O6 ' _chemical_formula_sum ' C16 H17 Br O6 ' _chemical_formula_structural ? _chemical_formula_analytical ' C16 H17 Br O6 ' _chemical_formula_weight 385.21 loop_ _chemical_melting_point 135 137 _symmetry_cell_setting 'orthorhombic' _symmetry_space_group_name_H-M ' P 21 21 21 ' _symmetry_space_group_name_Hall ? _cell_length_a 15.054(3) _cell_length_b 14.924(2) _cell_length_c 7.207(2) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 1619.2(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 30 _cell_measurement_theta_min 26 _cell_measurement_theta_max 52 _cell_measurement_temperature 293(2) _exptl_crystal_description ; Prismatic crystals ; _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.21 _exptl_crystal_density_diffrn 1.580 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_F_000 784.0 _exptl_absorpt_coefficient_mu 3.729 _exptl_absorpt_correction_type 'not applied' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_type 'Cu-K\a~1~' _diffrn_radiation_wavelength 1.540562 _diffrn_radiation_source 'standard Cu anode' _diffrn_radiation_monochromator 'Ni-filter' _diffrn_measurement_device 'Siemens-AED diffractometer' _diffrn_measurement_method '\q--2\q' _diffrn_reflns_number 3451 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_theta_min 3 _diffrn_reflns_theta_max 70 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_reduction_process ; Standard. Lp correction. Equivalent reflections merged. ; _diffrn_standards_number 1 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 4 7 2 _reflns_observed_criterion 'I>2\s(I)' _refine_ls_structure_factor_coef 'F' _refine_ls_matrix_type 'full' _refine_ls_R_factor_all ? _refine_ls_R_factor_obs 0.0431 _refine_ls_wR_factor_obs 0.0558 _refine_ls_goodness_of_fit_obs 0.7118 _refine_ls_number_reflns 2808 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_hydrogen_treatment 'refall' _refine_ls_weighting_scheme ? _refine_ls_shift/esd_max 0.003 _refine_ls_shift/esd_mean ? _refine_diff_density_max 0.66 _refine_diff_density_min -1.7 _refine_ls_abs_structure_Flack ? _refine_ls_abs_structure_Rogers ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Br Bromine -.767 1.283 'IT.4 Tab.2.2A 2.3.1' O Oxygen .047 .032 'IT.4 Tab.2.2A 2.3.1' C Carbon .017 .009 'IT.4 Tab.2.2A 2.3.1' H Hydrogen .000 .000 'IT.4 Tab.2.2C ' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol Br .15288(3) .54124(2) .21313(7) .05530(10) Uani . . Br O1 .1338(2) .7483(2) .1487(4) .0450(8) Uani . . O O2 .0330(2) .7756(2) .3804(4) .0367(6) Uani . . O O3 -.0135(2) .7110(2) -.0767(5) .0611(10) Uani . . O O4 -.0300(2) .8589(2) -.1264(5) .0561(9) Uani . . O O5 .0794(2) .9344(2) .5329(4) .0543(9) Uani . . O O6 .1181(3) .9888(2) .2554(5) .0729(13) Uani . . O C1 .1816(2) .7311(2) .4672(6) .0402(9) Uani . . C C2 .2424(2) .8018(3) .4450(7) .0504(13) Uani . . C C3 .3030(3) .8220(3) .5824(9) .0672(19) Uani . . C C4 .3048(3) .7702(4) .7443(8) .0713(18) Uani . . C C5 .2480(3) .6981(4) .7625(7) .0618(16) Uani . . C C6 .1853(2) .6776(3) .6259(6) .0438(10) Uani . . C C7 .1266(3) .5972(3) .6490(6) .0516(12) Uani . . C C8 .0455(2) .5961(2) .5238(6) .0441(10) Uani . . C C9 .0680(2) .6254(2) .3280(5) .0383(9) Uani . . C C10 .1072(2) .7195(2) .3282(5) .0347(9) Uani . . C C11 .0775(2) .8186(2) .0870(5) .0401(10) Uani . . C C12 .0347(2) .8532(2) .2668(5) .0388(9) Uani . . C C13 .0078(2) .7873(2) -.0477(6) .0427(10) Uani . . C C14 -.1028(3) .8408(5) -.2555(8) .0725(16) Uani . . C C15 .0839(3) .9329(2) .3495(6) .0448(11) Uani . . C C16 .1254(4) 1.0072(3) .6254(8) .0713(18) Uani . . C H2 .241(4) .839(5) .317(11) .09(2) Uiso . C2 H H3 .354(4) .883(4) .589(9) .083(17) Uiso . C3 H H4 .346(5) .796(5) .843(10) .10(2) Uiso . C4 H H5 .247(4) .657(4) .881(9) .066(15) Uiso . C5 H H71 .104(3) .595(3) .791(6) .13(3) Uiso . C7 H H72 .166(3) .538(3) .620(6) .084(18) Uiso . C7 H H81 -.009(3) .641(3) .579(7) .046(11) Uiso . C8 H H82 .014(3) .532(3) .531(6) .034(9) Uiso . C8 H H12 -.021(3) .874(3) .241(6) .038(10) Uiso . C12 H H11 .112(3) .862(3) .025(7) .049(12) Uiso . C11 H H91 .007(2) .626(2) .248(5) .071(16) Uiso . C9 H H141 -.128(3) .903(4) -.310(8) .09(2) Uiso . C14 H H142 -.079(3) .800(4) -.368(8) .12(3) Uiso . C14 H H143 -.155(3) .806(4) -.183(8) .19(5) Uiso . C14 H H161 .117(4) 1.001(3) .774(8) .11(3) Uiso . C16 H H162 .195(4) 1.004(3) .592(8) .09(2) Uiso . C16 H H163 .098(4) 1.070(3) .579(8) .087(19) Uiso . C16 H