Organocatalyzed Enantioselective Direct Mannich Reaction of α-Styrylacetates.
Guang, Jie; Rout, Saroj; Bihani, Manisha; Larson, Ariel J.; Arman, Hadi D.; Zhao, John C.-G.; Organic letters 18 (2016) 2648–2651; doi:10.1021/acs.orglett.6b01087

data_1555566
_publ_section_title
;
 Organocatalyzed Enantioselective Direct Mannich Reaction of
 \a-Styrylacetates.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2648
_journal_page_last               2651
_journal_paper_doi               10.1021/acs.orglett.6b01087
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C35 H30 F N O4 S, C2 H6 O S'
_chemical_formula_sum            'C37 H36 F N O5 S2'
_chemical_formula_weight         657.79
_chemical_name_systematic
;
 2-Methylnaphthalen-1-yl(S,E)-4-(4-fluorophenyl)-2-{(S)-[(4-methylphenyl)
sulfonamido](phenyl)methyl}but-3-enoate dimethyl sulfoxide solvate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                102.470(11)
_cell_angle_beta                 103.640(11)
_cell_angle_gamma                105.496(13)
_cell_formula_units_Z            2
_cell_length_a                   8.6308(13)
_cell_length_b                   13.950(2)
_cell_length_c                   15.866(3)
_cell_measurement_reflns_used    5018
_cell_measurement_temperature    293
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.7
_cell_volume                     1707.7(5)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
scan:
	Number of images: 240
	           Slice: -95.0000 - 25.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 180.0000
	             XTD: 35.0348
	          2theta: -35.0108
scan:
	Number of images: 124
	           Slice: -66.0000 - -4.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 270.0000
	             XTD: 35.0348
	          2theta: -35.0108
scan:
	Number of images: 114
	           Slice: -68.0000 - -11.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 90.0000
	             XTD: 35.0348
	          2theta: -35.0108
scan:
	Number of images: 108
	           Slice: -67.0000 - -13.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 270.0000
	             XTD: 35.0348
	          2theta: -35.0108
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.009782
_diffrn_orient_matrix_UB_12      -0.122975
_diffrn_orient_matrix_UB_13      -0.006934
_diffrn_orient_matrix_UB_21      0.077158
_diffrn_orient_matrix_UB_22      0.008320
_diffrn_orient_matrix_UB_23      -0.007069
_diffrn_orient_matrix_UB_31      -0.015951
_diffrn_orient_matrix_UB_32      0.013348
_diffrn_orient_matrix_UB_33      0.064678
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9462
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.494
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_min         2.534
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       plate
_exptl_crystal_F_000             692
_exptl_crystal_recrystallization_method
'crystallization by slow evaporation of dichloromethane and hexanes'
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         6244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0200P)^2^+2.4000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1389
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5128
_reflns_number_total             6244
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01087_si_002.cif
_cod_data_source_block           MMBEDMSO
_cod_database_code               1555566
_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.a Ternary CH refined with riding coordinates:
 C15(H15), C1(H1A)
2.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C16(H16), C10(H10), C7(H7), C14(H14), C32(H32), C11(H11), C17(H17),
 C28(H28), C3(H3), C13(H13), C12(H12), C6(H6), C33(H33), C4(H4), C30(H30),
 C29(H29), C19(H19), C23(H23), C22(H22), C20(H20)
2.c Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C8(H8A,H8B,H8C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              40961
_shelx_hkl_checksum              189
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'