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_1554883
_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         'C17 H20 O4'
_chemical_formula_sum            'C17 H20 O4'
_chemical_formula_weight         288.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-09
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-26 deposited with the CCDC.	2019-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.011(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1636(11)
_cell_length_b                   10.2486(7)
_cell_length_c                   12.3402(11)
_cell_measurement_reflns_used    1067
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.8820
_cell_measurement_theta_min      3.8960
_cell_volume                     1445.5(2)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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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      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -95.00  -60.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  178.0000  -90.0000 35

  2 omega  -46.00   28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000   60.0000 74

  3 omega  -22.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000 -120.0000 120
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0304056000
_diffrn_orient_matrix_UB_12      0.0488562000
_diffrn_orient_matrix_UB_13      -0.0191331000
_diffrn_orient_matrix_UB_21      -0.0414772000
_diffrn_orient_matrix_UB_22      -0.0051386000
_diffrn_orient_matrix_UB_23      -0.0565784000
_diffrn_orient_matrix_UB_31      -0.0348400000
_diffrn_orient_matrix_UB_32      0.0487453000
_diffrn_orient_matrix_UB_33      0.0131576000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5398
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.006
_diffrn_reflns_theta_min         3.352
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93267
_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    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0532
_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^)+(0.0494P)^2^+0.2871P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1438
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1825
_reflns_number_total             2846
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00353c2.cif
_cod_data_source_block           zhangzh_0907
_cod_database_code               1554883
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,
 H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              88892
_shelx_hkl_checksum              36466
_olex2_date_sample_data_collection 2018-09-07
_olex2_submission_special_instructions 'No special instructions were received'