Cobalt Catalysis for Enantioselective Cyclobutanone Construction.
Kim, Daniel K.; Riedel, Jan; Kim, Raphael S.; Dong, Vy M.; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b05327

data_4126283
_publ_section_title
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 Cobalt Catalysis for Enantioselective Cyclobutanone Construction.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b05327
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H22 O2'
_chemical_formula_sum            'C18 H22 O2'
_chemical_formula_weight         270.35
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-11-15
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.336(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9373(6)
_cell_length_b                   6.0706(2)
_cell_length_c                   16.2408(6)
_cell_measurement_reflns_used    9244
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.02
_cell_measurement_theta_min      2.82
_cell_volume                     1515.33(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26101
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         70.165
_diffrn_reflns_theta_min         2.821
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  0.6617
_exptl_absorpt_correction_T_min  0.5594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1206 before and 0.0577 after correction.
The Ratio of minimum to maximum transmission is 0.8454.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 2317 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_coef       0.0027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         5688
_refine_ls_number_restraints     107
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0375P)^2^+0.2678P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0785
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                5464
_reflns_number_total             5688
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b05327_si_002.cif
_cod_data_source_block           uci_vmd26x
_cod_database_code               4126283
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C11B-C10B = C10-C11 = C28-C29 = C29B-C28B
 1.54 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(C28B) = Uanis(C28)
4. Rigid body (RIGU) restrains
 O2, C8, C9, C10, C10B, C11, C11B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
 O4, C26, C27, C28, C28B, C29, C29B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H9BC)=Sof(H9BD)=Sof(C11B)=Sof(H11C)=Sof(H11D)=Sof(C10B)=Sof(H10C)=
 Sof(H10D)=1-FVAR(1)
 Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11A)=Sof(H11B)=
 FVAR(1)
 Sof(H27C)=Sof(H27D)=Sof(C28B)=Sof(H28C)=Sof(H28D)=Sof(C29B)=Sof(H29C)=
 Sof(H29D)=1-FVAR(2)
 Sof(H27A)=Sof(H27B)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(C29)=Sof(H29A)=Sof(H29B)=
 FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C6(H6), C24(H24)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C9(H9A,H9B), C9(H9BC,H9BD), C10(H10A,H10B),
 C11(H11A,H11B), C21(H21A,H21B), C23(H23A,H23B), C27(H27A,H27B), C27(H27C,H27D),
  C28(H28A,H28B), C29(H29A,H29B), C28B(H28C,H28D), C11B(H11C,H11D), C10B(H10C,
 H10D), C29B(H29C,H29D)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C32(H32),
 C33(H33), C34(H34), C35(H35), C36(H36)
6.d X=CH2 refined with riding coordinates:
 C1(H1A,H1B), C19(H19A,H19B)
6.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              99027
_shelx_hkl_checksum              22177
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'