#------------------------------------------------------------------------------ #$Date: 2020-04-08 04:30:33 +0300 (Wed, 08 Apr 2020) $ #$Revision: 250473 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/77/1557750.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_1557750 loop_ _publ_author_name 'Baek, Doohyun' 'Ryu, Huijeong' 'Ryu, Ji Yeon' 'Lee, Junseong' 'Stoltz, Brian M.' 'Hong, Sukwon' _publ_section_title ; Catalytic Enantioselective Synthesis of Tetrasubstituted Chromanones via Palladium-Catalyzed Asymmetric Conjugate Arylation Using Chiral Pyridine-Dihydroisoquinoline Ligands ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D0SC00412J _journal_year 2020 _chemical_formula_moiety 'C20 H22 O2' _chemical_formula_sum 'C20 H22 O2' _chemical_formula_weight 294.37 _chemical_name_systematic (S)-2-(4-(tert-butyl)phenyl)-2-methylchroman-4-one _chemical_properties_physical Heat-sensitive _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_Hall 'C 2y' _space_group_name_H-M_alt 'C 1 2 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014 _audit_update_record ; 2019-09-20 deposited with the CCDC. 2020-04-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.9349(17) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 23.2747(4) _cell_length_b 6.77810(10) _cell_length_c 10.2443(2) _cell_measurement_reflns_used 9930 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 25.42 _cell_measurement_theta_min 2.61 _cell_volume 1615.20(5) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_unetI/netI 0.0130 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -28 _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 12536 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.424 _diffrn_reflns_theta_min 1.751 _exptl_absorpt_coefficient_mu 0.076 _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.211 _exptl_crystal_description block _exptl_crystal_F_000 632 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Hexane' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.150 _refine_diff_density_max 0.147 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.045 _refine_ls_abs_structure_details ; Flack x determined using 1292 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.0(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 203 _refine_ls_number_reflns 2965 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0306 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0501P)^2^+0.4895P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0793 _refine_ls_wR_factor_ref 0.0802 _reflns_Friedel_coverage 0.827 _reflns_Friedel_fraction_full 0.996 _reflns_Friedel_fraction_max 0.987 _reflns_number_gt 2880 _reflns_number_total 2965 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc00412j2.cif _cod_data_source_block hsw58-1 _cod_original_sg_symbol_H-M 'C 2' _cod_database_code 1557750 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.985 _shelx_estimated_absorpt_t_max 0.989 _shelxl_version_number 2014-3 _shelx_res_file ; TITL hsw58-1 in C2 CELL 0.71073 23.27467 6.7781 10.2443 90 91.9349 90 ZERR 4 0.00041 0.0001 0.0002 0 0.0017 0 LATT -7 SYMM -X,+Y,-Z SFAC C H O UNIT 80 88 8 OMIT 0 0 1 L.S. 20 ACTA BOND FMAP 2 PLAN 5 SIZE 0.15 0.18 0.2 TEMP 23 WGHT 0.050051 0.489453 FVAR 0.18295 O1 3 0.823149 1.035805 0.407507 11.00000 0.04926 0.04059 = 0.03305 -0.01214 0.00536 -0.00503 O2 3 0.846736 0.774645 0.053112 11.00000 0.02130 0.03353 = 0.01931 0.00292 0.00021 -0.00164 C1 1 0.827646 0.961831 0.300182 11.00000 0.02263 0.02987 = 0.02863 -0.00080 -0.00061 0.00514 C2 1 0.800262 0.773207 0.262001 11.00000 0.01845 0.02701 = 0.02290 0.00165 -0.00158 0.00413 C3 1 0.809829 0.692676 0.138822 11.00000 0.01694 0.02599 = 0.02111 0.00484 -0.00186 0.00371 C4 1 0.889711 0.910937 0.107123 11.00000 0.02104 0.02703 = 0.02427 0.00300 0.00132 -0.00283 C5 1 0.859630 1.060556 0.192736 11.00000 0.02558 0.02291 = 0.03553 0.00362 -0.00188 0.00308 AFIX 23 H5A 2 0.887977 1.150255 0.230970 11.00000 -1.20000 H5B 2 0.832837 1.137491 0.138980 11.00000 -1.20000 AFIX 0 C6 1 0.761893 0.677559 0.343288 11.00000 0.02351 0.03677 = 0.02205 0.00290 0.00094 0.00370 AFIX 43 H6 2 0.755674 0.728306 0.425964 11.00000 -1.20000 AFIX 0 C7 1 0.733238 0.509552 0.302690 11.00000 0.02182 0.03826 = 0.02916 0.00801 0.00133 -0.00186 AFIX 43 H7 2 0.707974 0.446901 0.357603 11.00000 -1.20000 AFIX 0 C8 1 0.742445 0.434286 0.178585 11.00000 0.02444 0.02963 = 0.03519 0.00173 -0.00348 -0.00398 AFIX 43 H8 2 0.722799 0.321731 0.150520 11.00000 -1.20000 AFIX 0 C9 1 0.780482 0.524892 0.096416 11.00000 0.02423 0.03213 = 0.02442 -0.00149 -0.00195 0.00135 AFIX 43 H9 2 0.786305 0.473828 0.013645 11.00000 -1.20000 AFIX 0 C10 1 0.914022 1.009005 -0.013023 11.00000 0.03088 0.04162 = 0.03335 0.01292 0.00405 -0.00329 AFIX 137 H10A 2 0.883661 1.075011 -0.061415 11.00000 -1.50000 H10B 2 0.930860 0.910530 -0.067181 11.00000 -1.50000 H10C 2 0.942854 1.103230 0.013865 11.00000 -1.50000 AFIX 0 C11 1 0.936966 0.793824 0.179847 11.00000 0.01883 0.02656 = 0.02296 0.00193 0.00300 -0.00141 C12 1 0.950348 0.603826 0.140739 11.00000 0.02747 0.03503 = 0.03713 -0.01347 -0.01125 0.00399 AFIX 43 H12 2 0.927745 0.542655 0.076004 11.00000 -1.20000 AFIX 0 C13 1 0.996984 0.503678 0.196820 11.00000 0.02993 0.03005 = 0.04275 -0.01466 -0.00789 0.00739 AFIX 43 H13 2 1.004930 0.376566 0.168404 11.00000 -1.20000 AFIX 0 C14 1 1.032171 0.587472 0.294119 11.00000 0.01881 0.02433 = 0.02528 -0.00038 0.00040 -0.00137 C15 1 1.017945 0.776424 0.333752 11.00000 0.02739 0.02307 = 0.02679 -0.00153 -0.00516 -0.00379 AFIX 43 H15 2 1.040246 0.837151 0.399202 11.00000 -1.20000 AFIX 0 C16 1 0.971255 0.877380 0.278257 11.00000 0.02882 0.01998 = 0.03007 -0.00177 -0.00135 -0.00069 AFIX 43 H16 2 0.962852 1.003549 0.307756 11.00000 -1.20000 AFIX 0 C17 1 1.086227 0.480343 0.347707 11.00000 0.02094 0.02592 = 0.03145 -0.00073 -0.00155 0.00083 C18 1 1.132742 0.502628 0.245769 11.00000 0.02569 0.05424 = 0.06269 0.02068 0.01046 0.00810 AFIX 137 H18A 2 1.167356 0.438485 0.276762 11.00000 -1.50000 H18B 2 1.140285 0.640126 0.231793 11.00000 -1.50000 H18C 2 1.119642 0.443193 0.165075 11.00000 -1.50000 AFIX 0 C19 1 1.074722 0.260134 0.366725 11.00000 0.03412 0.03302 = 0.04431 0.00847 -0.00709 -0.00065 AFIX 137 H19A 2 1.044759 0.243277 0.427895 11.00000 -1.50000 H19B 2 1.109142 0.196814 0.399663 11.00000 -1.50000 H19C 2 1.063046 0.202144 0.284547 11.00000 -1.50000 AFIX 0 C20 1 1.108295 0.565444 0.477143 11.00000 0.04304 0.05118 = 0.05666 -0.01829 -0.02673 0.01729 AFIX 137 H20A 2 1.121094 0.698440 0.464206 11.00000 -1.50000 H20B 2 1.139787 0.486914 0.510680 11.00000 -1.50000 H20C 2 1.077948 0.564745 0.538320 11.00000 -1.50000 AFIX 0 HKLF 4 REM hsw58-1 in C2 REM R1 = 0.0306 for 2880 Fo > 4sig(Fo) and 0.0315 for all 2965 data REM 203 parameters refined using 1 restraints END WGHT 0.0443 0.5215 REM Highest difference peak 0.147, deepest hole -0.182, 1-sigma level 0.045 Q1 1 1.0574 0.5351 0.3209 11.00000 0.05 0.15 Q2 1 0.9214 1.0079 0.4614 11.00000 0.05 0.13 Q3 1 0.7952 1.1732 0.0220 11.00000 0.05 0.12 Q4 1 0.6443 0.4348 0.3151 11.00000 0.05 0.12 Q5 1 0.7743 1.0734 0.1033 11.00000 0.05 0.12 ; _shelx_res_checksum 63886 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _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 _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.82315(7) 1.0358(2) 0.40751(14) 0.0409(4) Uani 1 1 d . . . . . O2 O 0.84674(5) 0.77465(19) 0.05311(11) 0.0247(3) Uani 1 1 d . . . . . C1 C 0.82765(8) 0.9618(3) 0.30018(18) 0.0271(4) Uani 1 1 d . . . . . C2 C 0.80026(7) 0.7732(3) 0.26200(16) 0.0228(4) Uani 1 1 d . . . . . C3 C 0.80983(7) 0.6927(3) 0.13882(16) 0.0214(4) Uani 1 1 d . . . . . C4 C 0.88971(7) 0.9109(3) 0.10712(17) 0.0241(4) Uani 1 1 d . . . . . C5 C 0.85963(8) 1.0606(3) 0.19274(19) 0.0281(4) Uani 1 1 d . . . . . H5A H 0.8880 1.1503 0.2310 0.034 Uiso 1 1 calc R U . . . H5B H 0.8328 1.1375 0.1390 0.034 Uiso 1 1 calc R U . . . C6 C 0.76189(7) 0.6776(3) 0.34329(17) 0.0274(4) Uani 1 1 d . . . . . H6 H 0.7557 0.7283 0.4260 0.033 Uiso 1 1 calc R U . . . C7 C 0.73324(7) 0.5096(3) 0.30269(18) 0.0297(4) Uani 1 1 d . . . . . H7 H 0.7080 0.4469 0.3576 0.036 Uiso 1 1 calc R U . . . C8 C 0.74244(8) 0.4343(3) 0.17859(19) 0.0299(4) Uani 1 1 d . . . . . H8 H 0.7228 0.3217 0.1505 0.036 Uiso 1 1 calc R U . . . C9 C 0.78048(7) 0.5249(3) 0.09642(17) 0.0270(4) Uani 1 1 d . . . . . H9 H 0.7863 0.4738 0.0136 0.032 Uiso 1 1 calc R U . . . C10 C 0.91402(8) 1.0090(3) -0.01302(19) 0.0352(5) Uani 1 1 d . . . . . H10A H 0.8837 1.0750 -0.0614 0.053 Uiso 1 1 calc R U . . . H10B H 0.9309 0.9105 -0.0672 0.053 Uiso 1 1 calc R U . . . H10C H 0.9429 1.1032 0.0139 0.053 Uiso 1 1 calc R U . . . C11 C 0.93697(7) 0.7938(3) 0.17985(16) 0.0227(4) Uani 1 1 d . . . . . C12 C 0.95035(8) 0.6038(3) 0.1407(2) 0.0335(5) Uani 1 1 d . . . . . H12 H 0.9277 0.5427 0.0760 0.040 Uiso 1 1 calc R U . . . C13 C 0.99698(8) 0.5037(3) 0.1968(2) 0.0344(4) Uani 1 1 d . . . . . H13 H 1.0049 0.3766 0.1684 0.041 Uiso 1 1 calc R U . . . C14 C 1.03217(7) 0.5875(3) 0.29412(16) 0.0228(4) Uani 1 1 d . . . . . C15 C 1.01794(8) 0.7764(3) 0.33375(17) 0.0259(4) Uani 1 1 d . . . . . H15 H 1.0402 0.8372 0.3992 0.031 Uiso 1 1 calc R U . . . C16 C 0.97125(8) 0.8774(3) 0.27826(18) 0.0263(4) Uani 1 1 d . . . . . H16 H 0.9629 1.0035 0.3078 0.032 Uiso 1 1 calc R U . . . C17 C 1.08623(7) 0.4803(3) 0.34771(18) 0.0262(4) Uani 1 1 d . . . . . C18 C 1.13274(9) 0.5026(4) 0.2458(3) 0.0473(6) Uani 1 1 d . . . . . H18A H 1.1674 0.4385 0.2768 0.071 Uiso 1 1 calc R U . . . H18B H 1.1403 0.6401 0.2318 0.071 Uiso 1 1 calc R U . . . H18C H 1.1196 0.4432 0.1651 0.071 Uiso 1 1 calc R U . . . C19 C 1.07472(9) 0.2601(3) 0.3667(2) 0.0373(5) Uani 1 1 d . . . . . H19A H 1.0448 0.2433 0.4279 0.056 Uiso 1 1 calc R U . . . H19B H 1.1091 0.1968 0.3997 0.056 Uiso 1 1 calc R U . . . H19C H 1.0630 0.2021 0.2845 0.056 Uiso 1 1 calc R U . . . C20 C 1.10830(10) 0.5654(4) 0.4771(2) 0.0509(7) Uani 1 1 d . . . . . H20A H 1.1211 0.6984 0.4642 0.076 Uiso 1 1 calc R U . . . H20B H 1.1398 0.4869 0.5107 0.076 Uiso 1 1 calc R U . . . H20C H 1.0779 0.5647 0.5383 0.076 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0493(9) 0.0406(9) 0.0330(7) -0.0121(7) 0.0054(6) -0.0050(7) O2 0.0213(6) 0.0335(7) 0.0193(6) 0.0029(5) 0.0002(4) -0.0016(5) C1 0.0226(8) 0.0299(10) 0.0286(9) -0.0008(7) -0.0006(7) 0.0051(7) C2 0.0184(8) 0.0270(9) 0.0229(8) 0.0017(7) -0.0016(6) 0.0041(7) C3 0.0169(7) 0.0260(9) 0.0211(8) 0.0048(7) -0.0019(6) 0.0037(7) C4 0.0210(8) 0.0270(9) 0.0243(8) 0.0030(7) 0.0013(6) -0.0028(7) C5 0.0256(9) 0.0229(10) 0.0355(10) 0.0036(8) -0.0019(7) 0.0031(8) C6 0.0235(9) 0.0368(11) 0.0220(9) 0.0029(8) 0.0009(7) 0.0037(8) C7 0.0218(8) 0.0383(11) 0.0292(9) 0.0080(8) 0.0013(7) -0.0019(8) C8 0.0244(9) 0.0296(10) 0.0352(10) 0.0017(8) -0.0035(7) -0.0040(8) C9 0.0242(8) 0.0321(10) 0.0244(8) -0.0015(8) -0.0019(6) 0.0013(8) C10 0.0309(10) 0.0416(12) 0.0333(10) 0.0129(9) 0.0040(8) -0.0033(9) C11 0.0188(8) 0.0266(9) 0.0230(8) 0.0019(7) 0.0030(6) -0.0014(7) C12 0.0275(9) 0.0350(11) 0.0371(10) -0.0135(9) -0.0112(8) 0.0040(8) C13 0.0299(9) 0.0300(10) 0.0427(11) -0.0147(9) -0.0079(8) 0.0074(8) C14 0.0188(8) 0.0243(9) 0.0253(8) -0.0004(7) 0.0004(6) -0.0014(7) C15 0.0274(9) 0.0231(9) 0.0268(9) -0.0015(7) -0.0052(7) -0.0038(7) C16 0.0288(9) 0.0200(9) 0.0301(9) -0.0018(7) -0.0013(7) -0.0007(7) C17 0.0209(8) 0.0259(10) 0.0315(9) -0.0007(7) -0.0015(7) 0.0008(7) C18 0.0257(9) 0.0542(15) 0.0627(14) 0.0207(12) 0.0105(9) 0.0081(10) C19 0.0341(10) 0.0330(11) 0.0443(11) 0.0085(9) -0.0071(8) -0.0006(9) C20 0.0430(12) 0.0512(15) 0.0567(14) -0.0183(12) -0.0267(11) 0.0173(11) 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' 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O2 C4 116.87(12) . . ? O1 C1 C2 123.18(18) . . ? O1 C1 C5 122.50(18) . . ? C2 C1 C5 114.26(16) . . ? C3 C2 C6 118.66(17) . . ? C3 C2 C1 119.77(16) . . ? C6 C2 C1 121.46(16) . . ? O2 C3 C9 116.42(15) . . ? O2 C3 C2 122.90(16) . . ? C9 C3 C2 120.66(16) . . ? O2 C4 C10 103.81(14) . . ? O2 C4 C5 108.49(13) . . ? C10 C4 C5 111.36(16) . . ? O2 C4 C11 109.21(14) . . ? C10 C4 C11 109.83(14) . . ? C5 C4 C11 113.65(14) . . ? C1 C5 C4 111.86(16) . . ? C7 C6 C2 121.02(17) . . ? C6 C7 C8 119.38(17) . . ? C9 C8 C7 120.88(18) . . ? C8 C9 C3 119.38(16) . . ? C16 C11 C12 117.40(16) . . ? C16 C11 C4 121.96(16) . . ? C12 C11 C4 120.39(16) . . ? C11 C12 C13 120.96(18) . . ? C12 C13 C14 122.04(19) . . ? C15 C14 C13 116.52(17) . . ? C15 C14 C17 122.14(15) . . ? C13 C14 C17 121.21(17) . . ? C14 C15 C16 121.74(16) . . ? C11 C16 C15 121.31(17) . . ? C20 C17 C19 108.34(18) . . ? C20 C17 C18 109.30(18) . . ? C19 C17 C18 108.22(17) . . ? C20 C17 C14 112.37(16) . . ? C19 C17 C14 111.19(15) . . ? C18 C17 C14 107.32(15) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.216(2) . ? O2 C3 1.367(2) . ? O2 C4 1.457(2) . ? C1 C2 1.475(3) . ? C1 C5 1.506(3) . ? C2 C3 1.400(2) . ? C2 C6 1.401(3) . ? C3 C9 1.389(3) . ? C4 C10 1.524(2) . ? C4 C5 1.526(3) . ? C4 C11 1.530(2) . ? C6 C7 1.377(3) . ? C7 C8 1.393(3) . ? C8 C9 1.386(3) . ? C11 C16 1.386(2) . ? C11 C12 1.387(3) . ? C12 C13 1.388(3) . ? C13 C14 1.390(3) . ? C14 C15 1.387(3) . ? C14 C17 1.538(2) . ? C15 C16 1.389(3) . ? C17 C20 1.519(3) . ? C17 C19 1.530(3) . ? C17 C18 1.537(3) . ?