Highly stereoselective synthesis of 2,3-dihydrofurans via cascade Michael addition-alkylation process: nitro group as the leaving group
Mo, Yiran; Liu, Siyang; Liu, Yingying; Ye, Ling; Shi, Zhichuan; Zhao, Zhi-Gang; Li, Xuefeng; Chemical Communications  (2019) –; doi:10.1039/C9CC01509D

data_7123410
_publ_section_title
;
 Highly stereoselective synthesis of 2,3-dihydrofurans via cascade Michael
 addition-alkylation process: nitro group as the leaving group
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01509D
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_compound_source        EtOH
_chemical_formula_moiety         'C21 H18 O3'
_chemical_formula_sum            'C21 H18 O3'
_chemical_formula_weight         318.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2019-04-12 deposited with the CCDC.    2019-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5720(3)
_cell_length_b                   9.4216(2)
_cell_length_c                   20.1701(6)
_cell_measurement_reflns_used    2977
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.6440
_cell_measurement_theta_min      4.3610
_cell_volume                     1628.98(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -104.00 -20.00   1.00    1.00    --  -36.29 -57.00 -90.00   84
  2  \w    -94.00  -6.00   1.00    1.00    --  -36.29 132.00-167.00   88
  3  \w     20.00 104.00   1.00    1.00    --   36.29  57.00-180.00   84
  4  \w      1.00  75.00   1.00    1.00    --   36.29 -99.00 120.00   74
  5  \w     39.00 115.00   1.00    1.87    --  108.71-111.00   0.00   76
  6  \w     40.00 126.00   1.00    1.87    --  108.71 -45.00 150.00   86
  7  \w     91.00 177.00   1.00    1.87    --  108.71  45.00 -90.00   86
  8  \w     39.00 109.00   1.00    1.87    --  108.71 -94.00 150.00   70
  9  \w     39.00 115.00   1.00    1.87    --  108.71-111.00 -30.00   76
 10  \w     39.00 109.00   1.00    1.87    --  108.71 -94.00-120.00   70
 11  \w     91.00 166.00   1.00    1.87    --  108.71  45.00 150.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1667673000
_diffrn_orient_matrix_UB_12      0.0082976000
_diffrn_orient_matrix_UB_13      -0.0283121000
_diffrn_orient_matrix_UB_21      -0.0670831000
_diffrn_orient_matrix_UB_22      0.0270278000
_diffrn_orient_matrix_UB_23      -0.0697416000
_diffrn_orient_matrix_UB_31      0.0027360000
_diffrn_orient_matrix_UB_32      0.1609917000
_diffrn_orient_matrix_UB_33      0.0129924000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6074
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        64.207
_diffrn_reflns_theta_max         64.207
_diffrn_reflns_theta_min         4.384
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.690
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.298
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1001 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0955P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1327
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2544
_reflns_number_total             2684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01509d2.cif
_cod_data_source_block           lxf-190411-150k
_cod_original_cell_volume        1628.99(8)
_cod_database_code               7123410
_reflns_odcompleteness_completeness 99.94
_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
2.a Ternary CH refined with riding coordinates:
 C005(H005), C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00C,H00E), C00G(H00G,H00H), C00J(H00J,H00K)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00D(H00D), C00F(H00F), C00H(H00I), C00K(H00L),
 C00L(H00M), C00M(H00N), C00N(H00O), C00O(H00P)
;
_shelx_res_checksum              54143
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-04-11
_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 1.290
_oxdiff_exptl_absorpt_empirical_full_min 0.799