“On Water” Organocatalyzed [4 + 2] Cycloaddition of Enones and Nitro Dienes for the Enantioselective Synthesis of Densely Substituted Cyclohexanones
Vamisetti, Ganga B.; Chowdhury, Raghunath; Kumar, Mukesh; Ghosh, Sunil K.; Organic Letters  (2016) –; doi:10.1021/acs.orglett.6b00460

data_1543153
_publ_section_title
;
 &#x201C;On Water&#x201D; Organocatalyzed [4 + 2] Cycloaddition of Enones
 and Nitro Dienes for the Enantioselective Synthesis of Densely
 Substituted Cyclohexanones
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.6b00460
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H18 Cl N O3'
_chemical_formula_sum            'C20 H18 Cl N O3'
_chemical_formula_weight         355.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.297(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9375(5)
_cell_length_b                   12.3627(14)
_cell_length_c                   12.7571(11)
_cell_measurement_reflns_used    1220
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9870
_cell_measurement_theta_min      3.5320
_cell_volume                     924.12(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.3200
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
  1 omega  -15.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.6003  -38.0000 -150.0000 80

  2 omega  -29.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.6003  -19.0000  120.0000 99

  3 omega   42.00   77.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      101.9611  -45.0000   60.0000 35

  4 omega   32.00   69.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      101.9611  -30.0000    0.0000 37

  5 omega   30.00   57.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      101.9611  -30.0000 -150.0000 27

  6 omega   29.00   57.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      101.9611  -30.0000  -90.0000 28

  7 omega   29.00   64.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      101.9611  -30.0000  -30.0000 35

  8 omega   30.00   59.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      101.9611  -30.0000  150.0000 29

  9 omega   44.00   69.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      101.9611  -45.0000  120.0000 25

 10 omega   41.00   68.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      101.9611  -45.0000  -60.0000 27

 11 omega   31.00   56.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      101.9611  -30.0000 -120.0000 25

 12 omega   84.00  111.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      101.9611   30.0000  120.0000 27

 13 omega  123.00  152.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      101.9611   30.0000  120.0000 29

 14 omega   77.00  157.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      101.9611   61.0000  150.0000 80

 15 omega  132.00  158.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      101.9611    0.0000    0.0000 26

 16 omega   31.00   57.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      101.9611  -30.0000   90.0000 26

 17 omega   30.00   57.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      101.9611  -30.0000 -180.0000 27

 18 omega   79.00  105.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      101.9611    0.0000    0.0000 26
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Titan'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1932801000
_diffrn_orient_matrix_UB_12      0.0735792000
_diffrn_orient_matrix_UB_13      0.0547502000
_diffrn_orient_matrix_UB_21      -0.0605035000
_diffrn_orient_matrix_UB_22      -0.0303666000
_diffrn_orient_matrix_UB_23      0.1092200000
_diffrn_orient_matrix_UB_31      0.1674743000
_diffrn_orient_matrix_UB_32      -0.0959167000
_diffrn_orient_matrix_UB_33      0.0073075000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_av_unetI/netI     0.0895
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4368
_diffrn_reflns_point_group_measured_fraction_full 0.814
_diffrn_reflns_point_group_measured_fraction_max 0.781
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.291
_diffrn_reflns_theta_min         3.511
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.977
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.279
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.3689
_exptl_crystal_size_mid          0.1946
_exptl_crystal_size_min          0.0619
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 364 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2902
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0601
_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^)+(0.0484P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1741
_reflns_Friedel_coverage         0.536
_reflns_Friedel_fraction_full    0.612
_reflns_Friedel_fraction_max     0.574
_reflns_number_gt                1756
_reflns_number_total             2902
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00460_si_003.cif
_cod_data_source_block           vgb348_1_3l
_cod_database_code               1543153
_chemical_oxdiff_formula         'C20 H18 N O3 Cl'
_reflns_odcompleteness_completeness 99.83
_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:
 C9(H9), C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
;