Copper-catalyzed highly diastereoselective cross-dehydrogenative coupling between 8-hydroxyisochromanes and 1,3-dicarbonyl compounds
Zhang, Zhen; Tu, Yong-Qiang; Zhang, Xiao-Ming; Zhang, Fu-Min; Wang, Shao-Hua; Organic Chemistry Frontiers 6 (2019) 2275–; doi:10.1039/C9QO00353C

data_1554882
_publ_section_title
;
 Copper-catalyzed highly diastereoselective cross-dehydrogenative coupling
 between 8-hydroxyisochromanes and 1,3-dicarbonyl compounds
;
_journal_issue                   13
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2275
_journal_paper_doi               10.1039/C9QO00353C
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C14 H13 F3 O5'
_chemical_formula_sum            'C14 H13 F3 O5'
_chemical_formula_weight         318.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-02-26 deposited with the CCDC.	2019-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                68.951(11)
_cell_angle_beta                 83.144(9)
_cell_angle_gamma                83.818(8)
_cell_formula_units_Z            2
_cell_length_a                   6.4241(6)
_cell_length_b                   10.1906(11)
_cell_length_c                   11.3167(14)
_cell_measurement_reflns_used    1758
_cell_measurement_temperature    294.9(7)
_cell_measurement_theta_max      69.7930
_cell_measurement_theta_min      7.7920
_cell_volume                     684.79(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.9(7)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
  1 omega   29.00   66.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   30.0000 25

  2 omega  -26.00   28.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   30.0000 36

  3 omega  -76.00  -43.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000  -90.0000 22

  4 omega  -75.00  -42.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  150.0000 22

  5 omega  -38.00   11.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000  -90.0000 33

  6 omega  -15.00   37.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000   90.0000 35

  7 omega   12.00   85.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  120.0000 49

  8 omega   42.00  114.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 48

  9 omega  -15.00   81.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  -90.0000 64

 10 omega   85.00  172.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -180.0000 58

 11 omega  142.00  169.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   90.0000 -178.0000 18

 12 omega   85.00  145.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  150.0000 40

 13 omega   42.00   87.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 30

 14 omega  144.00  171.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   90.0000 18

 15 omega   50.00  140.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 60

 16 omega   43.00  163.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000  150.0000 80

 17 omega   47.00  101.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   30.0000 36

 18 omega   71.00  129.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  150.0000 39

 19 omega  107.00  146.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -120.0000 26

 20 omega   40.00  101.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 41

 21 omega   42.00   93.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 34

 22 omega   54.00   84.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 20

 23 omega   66.00   93.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 18

 24 omega  101.00  126.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   90.0000 -178.0000 17

 25 omega   52.00  115.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 42

 26 omega   57.00  105.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 32

 27 omega   86.00  129.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000    0.0000 29

 28 omega   68.00   93.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 17

 29 omega   44.00  114.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 47

 30 omega   69.00   94.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 17

 31 omega   72.00   99.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -120.0000 18
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0803328000
_diffrn_orient_matrix_UB_12      -0.1317185000
_diffrn_orient_matrix_UB_13      -0.0330514000
_diffrn_orient_matrix_UB_21      -0.0426705000
_diffrn_orient_matrix_UB_22      0.0805929000
_diffrn_orient_matrix_UB_23      -0.1397672000
_diffrn_orient_matrix_UB_31      0.2243941000
_diffrn_orient_matrix_UB_32      0.0502252000
_diffrn_orient_matrix_UB_33      -0.0284862000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4363
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         4.20
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.250
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0658P)^2^+0.1636P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1220
_reflns_number_gt                1958
_reflns_number_total             2341
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9qo00353c2.cif
_cod_data_source_block           zhangzh_0523
_cod_original_cell_volume        684.79(13)
_cod_database_code               1554882
_reflns_odcompleteness_completeness 96.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_date_sample_data_collection 2018-05-23
_olex2_submission_special_instructions 'No special instructions were received'