#------------------------------------------------------------------------------ #$Date: 2021-11-06 20:36:17 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270346 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/91/7129105.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7129105 loop_ _publ_author_name 'Del R\'io-Rodr\'iguez, Roberto' 'Laina-Mart\'in, V\'ictor' 'Fern\'andez-Salas, Jose A' 'Alem\'an, Jos\'e' _publ_section_title ; Enantioselective vinylogous Mukaiyama aldol reaction of \a-ketoesters under bifunctional organocatalysis. ; _journal_issue 88 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 11665 _journal_page_last 11668 _journal_paper_doi 10.1039/d1cc04263g _journal_volume 57 _journal_year 2021 _chemical_absolute_configuration ad _chemical_formula_sum 'C12 H13 Br O3' _chemical_formula_weight 285.13 _chemical_name_common RR-626-F1_200K _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_block_doi 10.5517/ccdc.csd.cc28jcsz _audit_update_record ; 2021-08-03 deposited with the CCDC. 2021-10-11 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.8320(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.3815(2) _cell_length_b 7.13240(10) _cell_length_c 10.0251(2) _cell_measurement_reflns_used 9956 _cell_measurement_temperature 200.(2) _cell_measurement_theta_max 26.1462 _cell_measurement_theta_min 2.5026 _cell_volume 581.92(2) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'shelXle (C.B. Huebschle, rev 994)' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 200.(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker Kappa Apex II' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_unetI/netI 0.0192 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 22324 _diffrn_reflns_theta_full 25.35 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_min 2.09 _diffrn_source 'sealed tube' _exptl_absorpt_coefficient_mu 3.521 _exptl_absorpt_correction_T_max 0.80 _exptl_absorpt_correction_T_min 0.66 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour 'clear colourless' _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 288 _exptl_crystal_size_max 0.218 _exptl_crystal_size_mid 0.192 _exptl_crystal_size_min 0.065 _refine_diff_density_max 0.317 _refine_diff_density_min -0.295 _refine_ls_abs_structure_details ; Flack x determined using 906 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.016(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.183 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 2111 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.183 _refine_ls_R_factor_all 0.0195 _refine_ls_R_factor_gt 0.0183 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0223P)^2^+0.1857P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.0547 _reflns_number_gt 2051 _reflns_number_total 2111 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1cc04263g2.cif _cod_data_source_block 03363 _cod_depositor_comments 'Adding full bibliography for 7129105.cif.' _cod_database_code 7129105 _shelx_res_file ; TITL 03363_0m_a.res in P2(1) 03363_0m.res created by SHELXL-2018/3 at 10:20:00 on 03-Aug-2021 CELL 0.71073 8.3815 7.1324 10.0251 90.000 103.832 90.000 ZERR 2.000 0.0002 0.0001 0.0002 0.000 0.001 0.000 LATT -1 SYMM -X, 1/2+Y, -Z SFAC C H Br O UNIT 24 26 2 6 LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! L.S. 20 ACTA BOND FMAP 2 PLAN 3 EQIV $1 x+1, y, z HTAB C2 Br1_$1 EQIV $2 -x+1, y-1/2, -z+2 HTAB C4 O3_$2 EQIV $3 -x+1, y+1/2, -z+1 HTAB O3 O2_$3 CONF SIZE 0.065 0.192 0.218 TEMP -72.980 WGHT 0.022300 0.185700 FVAR 0.29814 BR1 3 -0.122208 0.019061 0.761302 11.00000 0.05133 0.04936 = 0.05208 0.00250 0.01619 -0.01124 C1 1 0.541482 0.598243 0.577523 11.00000 0.04358 0.02788 = 0.03885 -0.00656 0.01886 -0.00497 C2 1 0.676514 0.497582 0.675796 11.00000 0.04006 0.04138 = 0.05722 -0.00463 0.01736 0.00479 AFIX 23 H2A 2 0.776193 0.577061 0.693162 11.00000 -1.20000 H2B 2 0.701529 0.380941 0.631267 11.00000 -1.20000 AFIX 0 C3 1 0.641467 0.446380 0.813715 11.00000 0.03871 0.04494 = 0.04404 0.00613 0.00129 0.00603 AFIX 23 H3A 2 0.573179 0.331645 0.804012 11.00000 -1.20000 H3B 2 0.745843 0.421539 0.882118 11.00000 -1.20000 AFIX 0 C4 1 0.551654 0.608116 0.861385 11.00000 0.03714 0.04562 = 0.03164 0.00128 0.00386 -0.00192 AFIX 23 H4A 2 0.621211 0.721886 0.871835 11.00000 -1.20000 H4B 2 0.530989 0.577818 0.952154 11.00000 -1.20000 AFIX 0 C5 1 0.389475 0.646648 0.759491 11.00000 0.03736 0.03495 = 0.02381 0.00016 0.01096 0.00257 C6 1 0.263443 0.492770 0.756564 11.00000 0.03238 0.03012 = 0.02528 0.00222 0.00822 0.00495 C7 1 0.216360 0.445824 0.877207 11.00000 0.04466 0.04728 = 0.02741 -0.00239 0.00975 -0.00453 AFIX 43 H7 2 0.263725 0.511187 0.959742 11.00000 -1.20000 AFIX 0 C8 1 0.102113 0.306005 0.878720 11.00000 0.04444 0.05001 = 0.02921 0.00285 0.01302 -0.00211 AFIX 43 H8 2 0.071568 0.275225 0.961414 11.00000 -1.20000 AFIX 0 C9 1 0.033448 0.212262 0.758644 11.00000 0.03305 0.03364 = 0.03793 0.00422 0.00937 0.00363 C10 1 0.074092 0.256455 0.637976 11.00000 0.04183 0.04199 = 0.03040 -0.00358 0.00673 -0.00143 AFIX 43 H10 2 0.024327 0.191984 0.555614 11.00000 -1.20000 AFIX 0 C11 1 0.188740 0.396417 0.637475 11.00000 0.04032 0.03738 = 0.02693 0.00264 0.01073 0.00375 AFIX 43 H11 2 0.216902 0.427190 0.553785 11.00000 -1.20000 AFIX 0 C12 1 0.317705 0.835733 0.786387 11.00000 0.05808 0.03481 = 0.03712 -0.00064 0.02177 0.00559 AFIX 23 H12A 2 0.220153 0.862584 0.711072 11.00000 -1.20000 H12B 2 0.280777 0.828018 0.872937 11.00000 -1.20000 AFIX 0 O1 4 0.413194 0.668084 0.619616 11.00000 0.03970 0.03910 = 0.02580 0.00412 0.01400 0.00515 O2 4 0.542067 0.625684 0.458782 11.00000 0.07431 0.05932 = 0.04295 0.00286 0.03465 0.00733 O3 4 0.430623 0.985295 0.796305 11.00000 0.08418 0.03542 = 0.04059 -0.00499 0.02338 -0.00901 AFIX 147 H3O 2 0.435225 1.019407 0.717114 11.00000 -1.50000 AFIX 0 HKLF 4 REM 03363_0m_a.res in P2(1) REM wR2 = 0.054703, GooF = S = 1.18316, Restrained GooF = 1.18286 for all data REM R1 = 0.018327 for 2051 Fo > 4sig(Fo) and 0.019515 for all 2111 data REM 146 parameters refined using 1 restraints END WGHT 0.0228 0.1826 REM Highest difference peak 0.317, deepest hole -0.295, 1-sigma level 0.052 Q1 1 -0.0535 0.0247 0.8441 11.00000 0.05 0.32 Q2 1 0.2037 0.5068 0.8072 11.00000 0.05 0.16 Q3 1 0.5823 0.5219 0.8388 11.00000 0.05 0.16 ; _shelx_res_checksum 82183 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' 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_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br Br1 -0.12221(4) 0.01906(8) 0.76130(4) 0.05028(14) Uani d . . . 1 . . C C1 0.5415(5) 0.5982(5) 0.5775(4) 0.0352(8) Uani d . . . 1 . . C C2 0.6765(4) 0.4976(8) 0.6758(4) 0.0452(9) Uani d . . . 1 . . H H2A 0.776193 0.577061 0.693162 0.054 Uiso calc U . R 1 . . H H2B 0.701529 0.380941 0.631267 0.054 Uiso calc U . R 1 . . C C3 0.6415(5) 0.4464(6) 0.8137(4) 0.0440(9) Uani d . . . 1 . . H H3A 0.573179 0.331645 0.804012 0.053 Uiso calc U . R 1 . . H H3B 0.745843 0.421539 0.882118 0.053 Uiso calc U . R 1 . . C C4 0.5517(5) 0.6081(6) 0.8614(4) 0.0389(8) Uani d . . . 1 . . H H4A 0.621211 0.721886 0.871835 0.047 Uiso calc U . R 1 . . H H4B 0.530989 0.577818 0.952154 0.047 Uiso calc U . R 1 . . C C5 0.3895(4) 0.6466(5) 0.7595(3) 0.0314(7) Uani d . . . 1 . . C C6 0.2634(4) 0.4928(6) 0.7566(3) 0.0290(7) Uani d . . . 1 . . C C7 0.2164(5) 0.4458(5) 0.8772(4) 0.0396(9) Uani d . . . 1 . . H H7 0.263725 0.511187 0.959742 0.048 Uiso calc U . R 1 . . C C8 0.1021(5) 0.3060(6) 0.8787(4) 0.0405(9) Uani d . . . 1 . . H H8 0.071568 0.275225 0.961414 0.049 Uiso calc U . R 1 . . C C9 0.0334(4) 0.2123(5) 0.7586(4) 0.0347(8) Uani d . . . 1 . . C C10 0.0741(5) 0.2565(5) 0.6380(4) 0.0384(8) Uani d . . . 1 . . H H10 0.024327 0.191984 0.555614 0.046 Uiso calc U . R 1 . . C C11 0.1887(5) 0.3964(5) 0.6375(3) 0.0344(8) Uani d . . . 1 . . H H11 0.216902 0.42719 0.553785 0.041 Uiso calc U . R 1 . . C C12 0.3177(5) 0.8357(5) 0.7864(4) 0.0416(9) Uani d . . . 1 . . H H12A 0.220153 0.862584 0.711072 0.05 Uiso calc U . R 1 . . H H12B 0.280777 0.828018 0.872937 0.05 Uiso calc U . R 1 . . O O1 0.4132(3) 0.6681(4) 0.6196(2) 0.0338(5) Uani d . . . 1 . . O O2 0.5421(4) 0.6257(5) 0.4588(3) 0.0554(8) Uani d . . . 1 . . O O3 0.4306(4) 0.9853(4) 0.7963(3) 0.0520(8) Uani d . . . 1 . . H H3O 0.435225 1.019407 0.717114 0.078 Uiso calc U . R 1 . . 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 0.0513(2) 0.0494(2) 0.0521(2) -0.0112(2) 0.01619(15) 0.0025(3) C1 0.044(2) 0.0279(16) 0.039(2) -0.0050(15) 0.0189(16) -0.0066(14) C2 0.0401(18) 0.041(3) 0.057(2) 0.005(2) 0.0174(15) -0.005(2) C3 0.039(2) 0.045(2) 0.044(2) 0.0060(17) 0.0013(17) 0.0061(16) C4 0.037(2) 0.046(2) 0.0316(19) -0.0019(17) 0.0039(16) 0.0013(16) C5 0.0374(19) 0.0349(19) 0.0238(16) 0.0026(15) 0.0110(14) 0.0002(14) C6 0.0324(14) 0.030(2) 0.0253(13) 0.0050(15) 0.0082(11) 0.0022(15) C7 0.045(2) 0.047(2) 0.0274(17) -0.0045(16) 0.0098(15) -0.0024(14) C8 0.044(2) 0.050(2) 0.0292(18) -0.0021(18) 0.0130(16) 0.0028(16) C9 0.0331(18) 0.0336(19) 0.0379(19) 0.0036(15) 0.0094(15) 0.0042(15) C10 0.042(2) 0.042(2) 0.0304(18) -0.0014(17) 0.0067(15) -0.0036(16) C11 0.0403(19) 0.0374(19) 0.0269(16) 0.0038(16) 0.0107(14) 0.0026(15) C12 0.058(2) 0.035(2) 0.037(2) 0.0056(18) 0.0218(18) -0.0006(16) O1 0.0397(13) 0.0391(14) 0.0258(12) 0.0051(11) 0.0140(10) 0.0041(10) O2 0.074(2) 0.0593(18) 0.0430(17) 0.0073(16) 0.0347(15) 0.0029(14) O3 0.0842(19) 0.035(2) 0.0406(13) -0.0090(15) 0.0234(13) -0.0050(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O2 C1 O1 . . 116.3(4) ? O2 C1 C2 . . 123.1(3) ? O1 C1 C2 . . 120.6(3) ? C1 C2 C3 . . 115.7(3) ? C4 C3 C2 . . 108.7(3) ? C3 C4 C5 . . 111.0(3) ? O1 C5 C4 . . 110.9(3) ? O1 C5 C6 . . 108.0(3) ? C4 C5 C6 . . 112.9(3) ? O1 C5 C12 . . 103.0(3) ? C4 C5 C12 . . 111.6(3) ? C6 C5 C12 . . 109.9(3) ? C11 C6 C7 . . 117.5(3) ? C11 C6 C5 . . 122.8(3) ? C7 C6 C5 . . 119.7(3) ? C8 C7 C6 . . 121.3(3) ? C9 C8 C7 . . 119.0(3) ? C10 C9 C8 . . 121.3(4) ? C10 C9 Br1 . . 119.7(3) ? C8 C9 Br1 . . 119.0(3) ? C9 C10 C11 . . 119.2(3) ? C10 C11 C6 . . 121.5(3) ? O3 C12 C5 . . 113.2(3) ? C1 O1 C5 . . 124.2(3) ? 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 C9 . 1.902(4) ? C1 O2 . 1.208(5) ? C1 O1 . 1.341(4) ? C1 C2 . 1.495(6) ? C2 C3 . 1.525(6) ? C3 C4 . 1.516(5) ? C4 C5 . 1.517(5) ? C5 O1 . 1.471(4) ? C5 C6 . 1.519(5) ? C5 C12 . 1.527(5) ? C6 C11 . 1.390(5) ? C6 C7 . 1.400(5) ? C7 C8 . 1.385(5) ? C8 C9 . 1.377(5) ? C9 C10 . 1.370(5) ? C10 C11 . 1.386(5) ? C12 O3 . 1.414(5) ? 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 C2 H2B Br1 1_655 0.99 3.10 3.813(5) 129.8 ? C4 H4B O3 2_647 0.99 2.55 3.510(5) 163.0 ? O3 H3O O2 2_656 0.84 1.97 2.806(4) 173.5 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O2 C1 C2 C3 . . . . -169.8(4) ? O1 C1 C2 C3 . . . . 12.0(6) ? C1 C2 C3 C4 . . . . -40.2(5) ? C2 C3 C4 C5 . . . . 60.7(4) ? C3 C4 C5 O1 . . . . -51.8(4) ? C3 C4 C5 C6 . . . . 69.6(4) ? C3 C4 C5 C12 . . . . -166.0(3) ? O1 C5 C6 C11 . . . . -0.3(4) ? C4 C5 C6 C11 . . . . -123.3(4) ? C12 C5 C6 C11 . . . . 111.4(4) ? O1 C5 C6 C7 . . . . -179.1(3) ? C4 C5 C6 C7 . . . . 57.9(4) ? C12 C5 C6 C7 . . . . -67.4(4) ? C11 C6 C7 C8 . . . . 1.3(6) ? C5 C6 C7 C8 . . . . -179.8(3) ? C6 C7 C8 C9 . . . . -0.2(6) ? C7 C8 C9 C10 . . . . -1.0(6) ? C7 C8 C9 Br1 . . . . 179.5(3) ? C8 C9 C10 C11 . . . . 1.1(6) ? Br1 C9 C10 C11 . . . . -179.5(3) ? C9 C10 C11 C6 . . . . 0.1(5) ? C7 C6 C11 C10 . . . . -1.2(5) ? C5 C6 C11 C10 . . . . 180.0(3) ? O1 C5 C12 O3 . . . . -67.6(4) ? C4 C5 C12 O3 . . . . 51.5(4) ? C6 C5 C12 O3 . . . . 177.5(3) ? O2 C1 O1 C5 . . . . 179.0(3) ? C2 C1 O1 C5 . . . . -2.7(5) ? C4 C5 O1 C1 . . . . 22.6(5) ? C6 C5 O1 C1 . . . . -101.6(3) ? C12 C5 O1 C1 . . . . 142.2(3) ?