Enantioselective Dearomative [3+2] Cycloaddition of 2-Nitrobenzofurans with Aldehyde-Derived Morita−Baylis−Hillman Carbonates
Guo, Hai-Ming; Yang, Xin-He; Li, Jianping; Wang, Dong-Chao; Xie, Ming-Sheng; Qu, Gui-Rong; Chemical Communications  (2019) –; doi:10.1039/C9CC04542B

data_7123784
_publ_section_title
;
 Enantioselective Dearomative [3+2] Cycloaddition of 2-Nitrobenzofurans
 with Aldehyde-Derived Morita&#x2212;Baylis&#x2212;Hillman Carbonates
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC04542B
_journal_year                    2019
_chemical_formula_moiety         'C20 H17 N O5'
_chemical_formula_sum            'C20 H17 N O5'
_chemical_formula_weight         351.35
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-28 deposited with the CCDC.    2019-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.08830(10)
_cell_length_b                   9.08830(10)
_cell_length_c                   41.3484(8)
_cell_measurement_reflns_used    15073
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2190
_cell_measurement_theta_min      2.1070
_cell_volume                     3415.26(8)
_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      100.00(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 0.993
_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   -115.00 -17.00   1.00    1.00    --  -41.11 -38.00 -90.00   98
  2  \w   -114.00 -60.00   1.00    1.00    --  -41.11-146.00 107.00   54
  3  \w    -66.00  33.00   1.00    1.00    --  -41.11  38.00   0.00   99
  4  \w     23.00  97.00   1.00    1.00    --   41.11-125.00 -90.00   74
  5  \w     25.00 109.00   1.00    1.00    --  106.95 -95.00-180.00   84
  6  \w     31.00 135.00   1.00    1.00    --  106.95 -30.00 150.00  104
  7  \w     79.00 178.00   1.00    1.00    --  106.95  30.00 120.00   99
  8  \w     31.00 140.00   1.00    1.00    --  106.95 -77.00-150.00  109
  9  \w     94.00 178.00   1.00    1.00    --  106.95 125.00-180.00   84
 10  \w     25.00 160.00   1.00    1.00    --  106.95 -15.00  30.00  135
 11  \w   -117.00  -9.00   1.00    1.00    --  -41.11 -77.00 150.00  108
 12  \w   -115.00 -17.00   1.00    1.00    --  -41.11 -38.00-180.00   98
;
_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      -0.1251312000
_diffrn_orient_matrix_UB_12      -0.0114687000
_diffrn_orient_matrix_UB_13      0.0250225000
_diffrn_orient_matrix_UB_21      -0.1144815000
_diffrn_orient_matrix_UB_22      0.0064270000
_diffrn_orient_matrix_UB_23      -0.0274755000
_diffrn_orient_matrix_UB_31      0.0041881000
_diffrn_orient_matrix_UB_32      -0.1688306000
_diffrn_orient_matrix_UB_33      -0.0027832000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            22632
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.747
_diffrn_reflns_theta_min         4.277
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73173
_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    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.796
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 1258 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_coef       0.0030(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0768
_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^)+(0.1246P)^2^+4.3748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2148
_refine_ls_wR_factor_ref         0.2155
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3364
_reflns_number_total             3424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04542b2.cif
_cod_data_source_block           yxh
_cod_original_cell_volume        3415.26(10)
_cod_database_code               7123784
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.915
_reflns_odcompleteness_completeness 99.95
_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. Rigid bond restraints
 O5, C12
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
O5 \\sim C12: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
4.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C3(H3), C2(H2), C17(H17), C18(H18), C14(H14), C11(H11),
 C15(H15)
4.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.391
_oxdiff_exptl_absorpt_empirical_full_min 0.711