Facile Synthesis of Chiral [2,3]-Fused Hydrobenzofuran via Asymmetric Cu(I)-Catalyzed Dearomative 1,3-Dipolar Cycloaddition
Liang, Lei; Niu, Hongying; Wang, Dong-Chao; Yang, Xinhe; Qu, Gui-Rong; Guo, Hai-Ming; Chemical Communications  (2018) –; doi:10.1039/C8CC09226E

data_7122716
_publ_section_title
;
 Facile Synthesis of Chiral [2,3]-Fused Hydrobenzofuran via Asymmetric
 Cu(I)-Catalyzed Dearomative 1,3-Dipolar Cycloaddition
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC09226E
_journal_year                    2018
_chemical_formula_moiety         'C18 H15 Cl N2 O5'
_chemical_formula_sum            'C18 H15 Cl N2 O5'
_chemical_formula_weight         374.77
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-08-28 deposited with the CCDC.
2018-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   11.0671(2)
_cell_length_b                   11.0671(2)
_cell_length_c                   11.8214(2)
_cell_measurement_reflns_used    7554
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      73.4300
_cell_measurement_theta_min      3.6980
_cell_volume                     1253.91(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -67.00  29.00   1.00    1.00    --  -40.98  57.00 -30.00   96
  2  \w    -34.00  -7.00   1.00    1.00    --  -40.98 125.00 -30.00   27
  3  \w    -60.00  26.00   1.00    1.00    --  -40.98  57.00-150.00   86
  4  \w     58.00  89.00   1.00    1.00    --   40.98-125.00   0.00   31
  5  \w     29.00 107.00   1.00    1.00    --  106.95 -94.00 120.00   78
  6  \w     49.00 121.00   1.00    1.00    --  106.95-125.00  60.00   72
  7  \w     33.00 118.00   1.00    1.00    --  106.95 -30.00  60.00   85
  8  \w     63.00 152.00   1.00    1.00    --  106.95  15.00   0.00   89
  9  \w     79.00 177.00   1.00    1.00    --  106.95  30.00-120.00   98
 10  \w    107.00 133.00   1.00    1.00    --  106.95 -45.00-150.00   26
 11  \w     48.00 108.00   1.00    1.00    --  106.95 -94.00-180.00   60
 12  \w     37.00  89.00   1.00    1.00    --  106.95 -45.00-150.00   52
 13  \w     37.00 139.00   1.00    1.00    --  106.95 -77.00-150.00  102
 14  \w     99.00 133.00   1.00    1.00    --  106.95 125.00 150.00   34
 15  \w    109.00 177.00   1.00    1.00    --  106.95 125.00-180.00   68
 16  \w   -111.00 -39.00   1.00    1.00    --  -40.98 -57.00  60.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0640565000
_diffrn_orient_matrix_UB_12      0.1424881000
_diffrn_orient_matrix_UB_13      0.0599878000
_diffrn_orient_matrix_UB_21      -0.0288654000
_diffrn_orient_matrix_UB_22      -0.0735747000
_diffrn_orient_matrix_UB_23      0.1155264000
_diffrn_orient_matrix_UB_31      0.1447069000
_diffrn_orient_matrix_UB_32      0.0117197000
_diffrn_orient_matrix_UB_33      -0.0036682000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8112
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.496
_diffrn_reflns_theta_min         4.614
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.329
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       block
_exptl_crystal_F_000             582
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1402 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3098
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0608P)^2^+0.1076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0785
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.876
_reflns_Friedel_fraction_max     0.850
_reflns_number_gt                3087
_reflns_number_total             3098
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09226e2.cif
_cod_data_source_block           ll_1
_cod_original_cell_volume        1253.91(5)
_cod_database_code               7122716
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C12(H12), C3(H3), C5(H5), C4(H4), C16(H16), C15(H15), C14(H14)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.700
_oxdiff_exptl_absorpt_empirical_full_min 0.650