“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_1543152
_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         'C21 H18 F3 N O3'
_chemical_formula_sum            'C21 H18 F3 N O3'
_chemical_formula_weight         389.36
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_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'
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Olex2 1.2
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
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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)
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_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)
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_diffrn_ambient_temperature      293(2)
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_diffrn_measured_fraction_theta_full 0.995
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  1 omega   39.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 38

  2 omega  -48.00    7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 55

  3 omega -156.00 -110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7289 -126.0000   60.0000 46

  4 omega  -68.00  -30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7289   30.0000 -150.0000 38

  5 omega -153.00 -112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7289  -95.0000  120.0000 41

  6 omega  -14.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7289   30.0000 -150.0000 58

  7 omega    2.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega  -45.00  -19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega   19.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577 -112.0000 -150.0000 95

 10 omega   59.00  143.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577   77.0000  120.0000 84

 11 omega   15.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -50.0000 -180.0000 66

 12 omega   72.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577   64.0000 -150.0000 79

 13 omega   85.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  112.0000   30.0000 26

 14 omega   72.00  156.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577   64.0000 -120.0000 84

 15 omega   11.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -38.0000   90.0000 58
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Titan'
_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_21      0.0717716000
_diffrn_orient_matrix_UB_22      0.0852866000
_diffrn_orient_matrix_UB_23      -0.0293293000
_diffrn_orient_matrix_UB_31      -0.2377303000
_diffrn_orient_matrix_UB_32      0.0330217000
_diffrn_orient_matrix_UB_33      0.0085305000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
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_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.995
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_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5982
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.973
_diffrn_reflns_theta_min         4.556
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.955
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_exptl_absorpt_correction_T_min  0.78164
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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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colourless
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_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.814
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
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 Flack x determined using 919 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(15)
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0857
_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^)+(0.1775P)^2^+0.3240P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                2804
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_cod_data_source_file            ol6b00460_si_003.cif
_cod_data_source_block           skg_babu4_3g
_cod_original_cell_volume        1876.44(16)
_cod_database_code               1543152
_chemical_oxdiff_formula         'C21 H18 F3 N O3'
_reflns_odcompleteness_completeness 99.65
_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:
 C8(H8), C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C14(H14), C15(H15), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
;