Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones
Xie, Lihua; Dong, Shunxi; Zhang, Qian; Feng, Xiaoming; Liu, Xiaohua; Chemical Communications  (2018) –; doi:10.1039/C8CC08985J

data_7122694
_publ_section_title
;
 Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via
 desymmetrization of p-quinols with azlactones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC08985J
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C H2 Cl2, C23 H21 N O4'
_chemical_formula_sum            'C24 H23 Cl2 N O4'
_chemical_formula_weight         460.33
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-11-07 deposited with the CCDC.
2018-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                75.516(4)
_cell_angle_beta                 69.837(4)
_cell_angle_gamma                89.852(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4955(4)
_cell_length_b                   11.2983(5)
_cell_length_c                   11.3062(5)
_cell_measurement_reflns_used    9307
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.9890
_cell_measurement_theta_min      4.9630
_cell_volume                     1097.76(9)
_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 0.999
_diffrn_measured_fraction_theta_max 0.986
_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  22.00   1.00    1.04    --    0.00 -68.00  30.57   89
  2  \w    -39.00  -4.00   1.00    1.04    --   16.00 128.00 131.67   35
  3  \w   -104.00 -20.00   1.00    1.04    --  -36.42 -57.00-120.00   84
  4  \w    -53.00  31.00   1.00    1.04    --  -36.42  57.00-180.00   84
  5  \w      1.00  75.00   1.00    1.04    --   36.42 -99.00 -90.00   74
  6  \w     23.00  90.00   1.00    1.04    --   36.42-125.00   0.00   67
  7  \w    -31.00  53.00   1.00    1.04    --   36.42 -57.00  30.00   84
  8  \w     23.00  90.00   1.00    1.04    --   36.42-125.00  30.00   67
  9  \w      1.00  75.00   1.00    1.04    --   36.42 -99.00 150.00   74
 10  \w      8.00  35.00   1.00    1.04    --   40.00  86.00  32.43   27
 11  \w      7.00  33.00   1.00    1.04    --   40.00  89.00-104.66   26
 12  \w      7.00  33.00   1.00    1.04    --   40.00  88.00 113.09   26
 13  \w     20.00  47.00   1.00    1.04    --   48.00  79.00-179.87   27
 14  \w     18.00  45.00   1.00    1.04    --   48.00  82.00 -38.76   27
 15  \w     26.00 119.00   1.00    1.04    --   52.00  75.00 102.58   93
 16  \w     26.00 119.00   1.00    1.04    --   52.00  76.00  -5.05   93
 17  \w     26.00 119.00   1.00    1.04    --   52.00  75.00 132.26   93
 18  \w     25.00 120.00   1.00    1.04    --   52.00  77.00-108.33   95
 19  \w     26.00 119.00   1.00    1.04    --   52.00  75.00-138.57   93
 20  \w     26.00 119.00   1.00    1.04    --   52.00  75.00 -71.70   93
 21  \w     26.00 119.00   1.00    1.04    --   52.00  75.00  47.94   93
 22  \w     31.00 123.00   1.00    1.04    --   56.00  74.00 146.65   92
 23  \w     31.00 123.00   1.00    1.04    --   56.00  73.00  76.00   92
 24  \w     33.00 128.00   1.00    1.04    --   60.00  77.00   9.16   95
 25  \w     82.00 176.00   1.00    4.17    --  108.71  77.00 -30.00   94
 26  \w     91.00 176.00   1.00    4.17    --  108.71  61.00  30.00   85
 27  \w     87.00 178.00   1.00    4.17    --  108.71  30.00 120.00   91
 28  \w     91.00 176.00   1.00    4.17    --  108.71  61.00 -90.00   85
 29  \w     39.00 109.00   1.00    4.17    --  108.71 -94.00 -30.00   70
 30  \w     91.00 176.00   1.00    4.17    --  108.71  61.00 -30.00   85
 31  \w     82.00 176.00   1.00    4.17    --  108.71  77.00  30.00   94
 32  \w     91.00 176.00   1.00    4.17    --  108.71  61.00 150.00   85
 33  \w     82.00 176.00   1.00    4.17    --  108.71  77.00 150.00   94
 34  \w     91.00 176.00   1.00    4.17    --  108.71  61.00-120.00   85
 35  \w     39.00 109.00   1.00    4.17    --  108.71 -94.00 150.00   70
 36  \w     82.00 176.00   1.00    4.17    --  108.71  77.00  90.00   94
 37  \w     91.00 176.00   1.00    4.17    --  108.71  61.00   0.00   85
 38  \w     82.00 176.00   1.00    4.17    --  108.71  77.00 -60.00   94
 39  \w     42.00 127.00   1.00    4.17    --  108.71 -61.00-180.00   85
 40  \w     82.00 176.00   1.00    4.17    --  108.71  77.00-180.00   94
 41  \w     42.00 127.00   1.00    4.17    --  108.71 -61.00   0.00   85
 42  \w     82.00 176.00   1.00    4.17    --  108.71  77.00-120.00   94
 43  \w     82.00 176.00   1.00    4.17    --  108.71  77.00-150.00   94
 44  \w     82.00 176.00   1.00    4.17    --  108.71  77.00   0.00   94
 45  \w     77.00 106.00   1.00    4.17    --  108.71-111.00 -90.00   29
 46  \w    137.00 163.00   1.00    4.17    --  108.71  77.00 -90.00   26
 47  \w     91.00 169.00   1.00    4.17    --  108.71  61.00  60.00   78
 48  \w     91.00 119.00   1.00    4.17    --  108.71  61.00 120.00   28
 49  \w     82.00 108.00   1.00    4.17    --  108.71  77.00 -90.00   26
 50  \w     91.00 150.00   1.00    4.17    --  108.71  61.00 -60.00   59
 51  \w     82.00 108.00   1.00    4.17    --  108.71  77.00  60.00   26
 52  \w     84.00 176.00   1.00    4.17    --  108.71  77.00 120.00   92
 53  \w     74.00 105.00   1.00    4.17    --  108.71 -94.00  60.00   31
 54  \w     91.00 116.00   1.00    4.17    --  108.71  61.00-150.00   25
;
_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      -0.1680503000
_diffrn_orient_matrix_UB_12      -0.0007433000
_diffrn_orient_matrix_UB_13      0.0808970000
_diffrn_orient_matrix_UB_21      0.0413951000
_diffrn_orient_matrix_UB_22      0.0074438000
_diffrn_orient_matrix_UB_23      0.1184349000
_diffrn_orient_matrix_UB_31      0.0129469000
_diffrn_orient_matrix_UB_32      0.1412270000
_diffrn_orient_matrix_UB_33      -0.0458503000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22281
_diffrn_reflns_point_group_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.991
_diffrn_reflns_theta_min         4.058
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.923
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05095
_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    1.393
_exptl_crystal_description       needle
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 3005 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         7754
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0547
_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^)+(0.1008P)^2^+0.0567P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_full    0.807
_reflns_Friedel_fraction_max     0.783
_reflns_number_gt                7442
_reflns_number_total             7754
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc08985j2.cif
_cod_data_source_block           fxm-xxx-150k
_cod_original_cell_volume        1097.76(8)
_cod_database_code               7122694
_reflns_odcompleteness_completeness 99.97
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G), C00P(H00P)
2.b Secondary CH2 refined with riding coordinates:
 C015(H01A,H01B), C019(H01M,H01O), C01D(H01P,H01Q), C01F(H01E,H01F), C01P(H01Z,
 H), C01Q(H01Y,HA)
2.c Aromatic/amide H refined with riding coordinates:
 N00B(H00B), N00C(H00C), C00L(H00L), C00Q(H00Q), C00R(H00R), C00T(H00T),
 C00V(H00V), C00W(H00W), C00Y(H00Y), C00Z(H00Z), C010(H010), C012(H012),
 C013(H013), C016(H016), C017(H017), C018(H018), C01A(H01C), C01B(H01D),
 C01E(H01R), C01G(H01G), C01H(H01S), C01I(H01I), C01J(H01T), C01K(H01U),
 C01L(H01L), C01N(H01N)
2.d Idealised Me refined as rotating group:
 C01M(H01H,H01J,H01K), C01O(H01V,H01W,H01X)
;
_shelx_res_checksum              85915
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2018-11-06
_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 13.439
_oxdiff_exptl_absorpt_empirical_full_min 0.606