Stereospecific Synthesis of Tetrahydronaphtho[2,3-b]furans Enabled by a Nickel-Promoted Tandem Reductive Cyclization.
Peng, Yu; Xiao, Jian; Xu, Xiao-Bo; Duan, Shu-Ming; Ren, Li; Shao, Yong-Liang; Wang, Ya-Wen; Organic letters 18 (2016) 5170–5173; doi:10.1021/acs.orglett.6b02665

data_1555849
_publ_section_title
;
 Stereospecific Synthesis of Tetrahydronaphtho[2,3-b]furans Enabled by a
 Nickel-Promoted Tandem Reductive Cyclization.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5170
_journal_page_last               5173
_journal_paper_doi               10.1021/acs.orglett.6b02665
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C16 H22 O4'
_chemical_formula_sum            'C16 H22 O4'
_chemical_formula_weight         278.33
_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             2016-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.350(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.983(2)
_cell_length_b                   5.7576(5)
_cell_length_c                   10.4224(11)
_cell_measurement_reflns_used    993
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.1260
_cell_measurement_theta_min      3.6220
_cell_volume                     1533.8(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -56.00  -20.00   1.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -57.0000  -60.0000 24

  2 omega    5.00   92.00   1.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   77.0000 -180.0000 58

  3 omega  -46.00   57.50   1.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -77.0000   60.0000 69
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0117686000
_diffrn_orient_matrix_UB_12      -0.0887385000
_diffrn_orient_matrix_UB_13      -0.0320479000
_diffrn_orient_matrix_UB_21      0.0246799000
_diffrn_orient_matrix_UB_22      0.0267062000
_diffrn_orient_matrix_UB_23      0.0384454000
_diffrn_orient_matrix_UB_31      -0.0047350000
_diffrn_orient_matrix_UB_32      -0.0811042000
_diffrn_orient_matrix_UB_33      0.0478002000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5615
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.188
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
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    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3121
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1725
_refine_ls_R_factor_gt           0.0845
_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^)+(0.1100P)^2^+0.4413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2153
_refine_ls_wR_factor_ref         0.2818
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1366
_reflns_number_total             3121
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02665_si_003.cif
_cod_data_source_block           0403
_cod_database_code               1555849
_reflns_odcompleteness_completeness 99.68
_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
2. Restrained distances
 C12-O4'
 1.2 with sigma of 0.01
 O4'-C13'
 1.3 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C14) \\sim Ueq, Uanis(C14') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O4') \\sim Ueq, Uanis(C13') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: H12(0.9) H12A(0.1) O4(0.9) C13(0.85) H13A(0.85) H13B(0.85)
 C14(0.75) H14A(0.75) H14B(0.75) H14C(0.75) O4'(0.1) C13'(0.15) H13C(0.15)
 H13D(0.15) C14'(0.25) H14D(0.25) H14E(0.25) H14F(0.25)
5.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C12(H12), C12(H12A)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C13'(H13C,H13D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5)
5.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C14(H14A,H14B,H14C), C14'(H14D,H14E,
 H14F)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'