#------------------------------------------------------------------------------ #$Date: 2009-11-18 16:56:34 +0200 (Wed, 18 Nov 2009) $ #$Revision: 858 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2209999.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_2209999 loop_ _publ_author_name 'Constable, Edwin C.' 'Housecroft, Catherine E.' 'Mahmood, Azad' 'Neuburger, Markus' 'Schaffner, Silvia' _publ_section_title ; 2,3,5,-Tri-O-acetyl-1-(2-chloroethyl)-\b-D-ribofuranose ; _journal_coeditor_code SG2041 _journal_issue 8 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o3151 _journal_page_last o3153 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C13 H19 Cl1 O8' _chemical_formula_moiety 'C13 H19 Cl1 O8' _chemical_formula_sum 'C13 H19 Cl O8' _[local]_cod_chemical_formula_sum_orig 'C13 H19 Cl1 O8' _chemical_formula_weight 338.74 _chemical_name_systematic ; 2,3,5,-Tri-O-acetyl-1-(2-chloroethyl)-\b-D-ribofuranose ; _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 _audit_creation_method CRYSTALS_ver_12.84 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.3407(5) _cell_length_b 13.5532(14) _cell_length_c 15.4384(9) _cell_measurement_reflns_used 2300 _cell_measurement_temperature 173 _cell_measurement_theta_max 29 _cell_measurement_theta_min 3 _cell_volume 1536.0(2) _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 2001)' _computing_data_reduction DENZO/SCALEPACK _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material CRYSTALS _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 173 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.075 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 46023 _diffrn_reflns_theta_full 28.503 _diffrn_reflns_theta_max 28.503 _diffrn_reflns_theta_min 3.006 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.286 _exptl_absorpt_correction_T_max 0.94 _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.465 _exptl_crystal_description block _exptl_crystal_F_000 712 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.20 _refine_diff_density_min -0.18 _refine_ls_abs_structure_details 'Flack (1983), with 1663 Friedel-pairs' _refine_ls_abs_structure_Flack -0.01(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.0728 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 2801 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0290 _refine_ls_shift/su_max 0.000484 _refine_ls_structure_factor_coef F _refine_ls_weighting_details ; w = [1-(F~o~-F~c~)^2^/36\s^2^(F)]^2^/[2.46T~o~(x)- 0.945T~1~(x)+1.98T~2~(x)-0.132T~3~(x)+0.288T~4~(x)], where T~i~ are the Chebychev polynomials and x = F~c~/F~max~ (Prince, 1982; Watkin, 1994) ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0340 _refine_ls_wR_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0326 _reflns_number_gt 2801 _reflns_number_total 3896 _reflns_threshold_expression I>3\s(I) _[local]_cod_data_source_file sg2041.cif 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_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4' loop_ _atom_site_type_symbol _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_occupancy Cl Cl1 -0.17803(9) 0.77456(5) 0.70851(3) 0.0462 Uani 1.0000 C C1 -0.0403(2) 0.66542(13) 0.97976(10) 0.0218 Uani 1.0000 C C2 -0.1299(2) 0.56750(12) 0.99970(10) 0.0214 Uani 1.0000 C C3 0.0022(2) 0.49744(12) 0.95621(10) 0.0190 Uani 1.0000 C C4 0.1855(2) 0.54351(12) 0.97671(10) 0.0203 Uani 1.0000 C C5 0.3353(2) 0.52188(13) 0.91281(11) 0.0254 Uani 1.0000 C C6 -0.0506(3) 0.79044(13) 0.87353(12) 0.0250 Uani 1.0000 C C7 -0.1898(3) 0.83112(14) 0.81275(11) 0.0284 Uani 1.0000 C C8 0.3415(3) 0.63447(13) 0.79545(12) 0.0271 Uani 1.0000 C C9 0.2838(3) 0.64797(17) 0.70370(13) 0.0392 Uani 1.0000 C C10 -0.1312(2) 0.33920(13) 0.95749(10) 0.0221 Uani 1.0000 C C11 -0.1098(3) 0.23765(13) 0.99245(13) 0.0278 Uani 1.0000 C C12 -0.2618(3) 0.50901(14) 1.13072(11) 0.0263 Uani 1.0000 C C13 -0.2348(3) 0.50509(18) 1.22664(12) 0.0394 Uani 1.0000 O O1 -0.09964(18) 0.69256(9) 0.89716(8) 0.0253 Uani 1.0000 O O2 0.15018(16) 0.64701(9) 0.98146(8) 0.0236 Uani 1.0000 O O3 0.28216(16) 0.54702(9) 0.82603(8) 0.0249 Uani 1.0000 O O4 0.4309(2) 0.69079(12) 0.83609(10) 0.0433 Uani 1.0000 O O5 -0.00059(17) 0.39937(8) 0.99004(8) 0.0217 Uani 1.0000 O O6 -0.24413(18) 0.36722(10) 0.90784(9) 0.0292 Uani 1.0000 O O7 -0.12075(17) 0.55489(10) 1.09188(8) 0.0254 Uani 1.0000 O O8 -0.3907(2) 0.47818(12) 1.09234(9) 0.0400 Uani 1.0000 H H11 -0.0696 0.7170 1.0195 0.0220 Uiso 1.0000 H H21 -0.2546 0.5586 0.9826 0.0223 Uiso 1.0000 H H31 -0.0280 0.4906 0.8969 0.0203 Uiso 1.0000 H H41 0.2332 0.5153 1.0283 0.0211 Uiso 1.0000 H H51 0.4399 0.5610 0.9276 0.0273 Uiso 1.0000 H H52 0.3669 0.4531 0.9154 0.0273 Uiso 1.0000 H H61 -0.0414 0.8301 0.9241 0.0262 Uiso 1.0000 H H62 0.0651 0.7895 0.8448 0.0262 Uiso 1.0000 H H71 -0.1673 0.9007 0.8067 0.0298 Uiso 1.0000 H H72 -0.3079 0.8211 0.8378 0.0298 Uiso 1.0000 H H91 0.1637 0.6213 0.6961 0.0483 Uiso 1.0000 H H92 0.2829 0.7170 0.6898 0.0483 Uiso 1.0000 H H93 0.3673 0.6142 0.6661 0.0483 Uiso 1.0000 H H111 -0.0198 0.2029 0.9592 0.0346 Uiso 1.0000 H H112 -0.0718 0.2409 1.0519 0.0346 Uiso 1.0000 H H113 -0.2241 0.2035 0.9887 0.0346 Uiso 1.0000 H H131 -0.1188 0.5344 1.2399 0.0420 Uiso 1.0000 H H132 -0.3303 0.5423 1.2536 0.0420 Uiso 1.0000 H H133 -0.2373 0.4382 1.2470 0.0420 Uiso 1.0000 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 Cl1 0.0582(3) 0.0568(3) 0.0236(2) 0.0061(3) 0.0007(2) 0.0029(2) C1 0.0245(8) 0.0220(8) 0.0190(7) 0.0015(7) -0.0001(6) -0.0002(6) C2 0.0208(8) 0.0247(8) 0.0187(7) -0.0017(7) -0.0017(6) 0.0027(6) C3 0.0226(8) 0.0183(8) 0.0160(7) -0.0027(6) -0.0019(6) 0.0030(6) C4 0.0216(8) 0.0203(8) 0.0190(7) -0.0009(6) -0.0034(7) 0.0024(6) C5 0.0230(8) 0.0275(9) 0.0257(8) 0.0036(7) 0.0007(7) 0.0049(7) C6 0.0284(9) 0.0196(9) 0.0271(8) 0.0003(7) 0.0014(7) 0.0019(7) C7 0.0332(10) 0.0258(9) 0.0263(8) 0.0046(8) 0.0047(8) 0.0043(7) C8 0.0274(9) 0.0257(8) 0.0281(8) 0.0017(7) 0.0107(8) 0.0006(7) C9 0.0468(13) 0.0418(12) 0.0289(9) 0.0053(9) 0.0040(9) 0.0082(9) C10 0.0246(8) 0.0227(8) 0.0190(7) -0.0027(7) 0.0038(7) -0.0015(6) C11 0.0295(9) 0.0223(8) 0.0317(9) -0.0044(7) 0.0002(7) 0.0032(7) C12 0.0321(9) 0.0210(8) 0.0257(8) 0.0053(7) 0.0086(7) 0.0022(7) C13 0.0486(12) 0.0459(12) 0.0237(9) 0.0094(10) 0.0109(8) 0.0042(8) O1 0.0335(7) 0.0199(6) 0.0226(6) -0.0014(5) -0.0056(5) 0.0032(5) O2 0.0225(6) 0.0198(6) 0.0284(6) -0.0036(5) -0.0016(5) -0.0023(5) O3 0.0280(6) 0.0262(6) 0.0205(6) -0.0012(5) 0.0023(5) 0.0010(5) O4 0.0523(9) 0.0409(9) 0.0367(8) -0.0211(7) 0.0091(7) -0.0027(7) O5 0.0258(6) 0.0183(5) 0.0209(6) -0.0030(5) -0.0037(5) 0.0027(4) O6 0.0300(7) 0.0267(6) 0.0309(7) -0.0054(5) -0.0079(6) 0.0018(5) O7 0.0274(6) 0.0321(7) 0.0166(5) -0.0012(5) 0.0014(5) 0.0010(5) O8 0.0378(8) 0.0497(9) 0.0325(7) -0.0160(7) 0.0052(6) 0.0058(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C7 1.7847(19) yes C1 C2 1.513(2) yes C1 O1 1.397(2) yes C1 O2 1.421(2) yes C1 H11 0.955 no C2 C3 1.515(2) yes C2 O7 1.435(2) yes C2 H21 0.960 no C3 C4 1.516(2) yes C3 O5 1.428(2) yes C3 H31 0.946 no C4 C5 1.506(2) yes C4 O2 1.428(2) yes C4 H41 0.950 no C5 O3 1.436(2) yes C5 H52 0.961 no C6 C7 1.493(3) no C6 O1 1.422(2) no C6 H62 0.958 no C7 H72 0.959 no C8 C9 1.490(3) no C8 O3 1.348(2) no C8 O4 1.186(2) no C9 H91 0.960 no C9 H92 0.960 no C9 H93 0.960 no C10 C11 1.487(2) no C10 O5 1.355(2) no C10 O6 1.191(2) no C11 H111 0.960 no C11 H112 0.960 no C11 H113 0.960 no C12 C13 1.495(3) no C12 O7 1.348(2) no C12 O8 1.192(2) no C13 H132 0.958 no C13 H133 0.960 no 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 C1 O1 106.34(13) yes C2 C1 O2 105.66(14) yes O1 C1 O2 111.71(13) yes C2 C1 H11 114.5 no O1 C1 H11 108.9 no O2 C1 H11 109.8 no C1 C2 C3 100.45(14) yes C1 C2 O7 106.62(13) yes C3 C2 O7 109.57(13) yes C1 C2 H21 117.9 no C3 C2 H21 114.2 no O7 C2 H21 107.6 no C2 C3 C4 102.56(13) yes C2 C3 O5 114.33(13) yes C4 C3 O5 108.65(13) yes C2 C3 H31 109.9 no C4 C3 H31 116.8 no O5 C3 H31 105.0 no C3 C4 C5 115.53(14) yes C3 C4 O2 104.72(13) yes C5 C4 O2 110.94(13) yes C3 C4 H41 109.7 no C5 C4 H41 101.6 no O2 C4 H41 114.8 no C4 C5 O3 111.48(14) no C4 C5 H52 109.7 no O3 C5 H52 109.5 no C7 C6 O1 109.42(15) no C7 C6 H62 108.7 no O1 C6 H62 109.3 no C6 C7 Cl1 112.03(13) no C6 C7 H72 108.3 no Cl1 C7 H72 110.3 no C9 C8 O3 110.43(17) no C9 C8 O4 125.54(18) no O3 C8 O4 124.01(18) no C8 C9 H91 109.4 no C8 C9 H92 109.5 no H91 C9 H92 109.5 no C8 C9 H93 109.5 no H91 C9 H93 109.5 no H92 C9 H93 109.5 no C11 C10 O5 110.36(14) no C11 C10 O6 127.02(16) no O5 C10 O6 122.62(16) no C10 C11 H111 109.4 no C10 C11 H112 109.6 no H111 C11 H112 109.5 no C10 C11 H113 109.4 no H111 C11 H113 109.5 no H112 C11 H113 109.5 no C13 C12 O7 110.78(18) no C13 C12 O8 125.82(18) no O7 C12 O8 123.38(16) no C12 C13 H132 108.3 no C12 C13 H133 110.9 no H132 C13 H133 109.9 no C6 O1 C1 113.63(13) no C4 O2 C1 110.50(12) yes C5 O3 C8 116.57(14) no C3 O5 C10 115.77(13) no C2 O7 C12 117.38(14) no