Synthesis of Difluoroalkyl Unsaturated β-Amino Acid Derivatives Exclusively through Alkyne Difunctionalization.
Wang, Qiang; Jin, Jia-Ni; Chen, Xi; Wang, Xin-Gang; Zhang, Bo-Sheng; Ma, Jun-Wei; Liang, Yong-Min; The Journal of organic chemistry 83 (2018) 14626–14636; doi:10.1021/acs.joc.8b02440

data_4035692
_publ_section_title
;
 Synthesis of Difluoroalkyl Unsaturated \b-Amino Acid Derivatives
 Exclusively through Alkyne Difunctionalization.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14626
_journal_page_last               14636
_journal_paper_doi               10.1021/acs.joc.8b02440
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C13 H19 F2 N O5'
_chemical_formula_sum            'C13 H19 F2 N O5'
_chemical_formula_weight         307.29
_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   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                92.577(13)
_cell_angle_beta                 94.129(16)
_cell_angle_gamma                93.294(13)
_cell_formula_units_Z            2
_cell_length_a                   5.7929(11)
_cell_length_b                   10.1326(13)
_cell_length_c                   13.119(3)
_cell_measurement_reflns_used    1617
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.1650
_cell_measurement_theta_min      3.7860
_cell_volume                     765.8(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -51.00  -25.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273   77.0000 -150.0000 13

  2 omega   25.00   51.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273   77.0000 -150.0000 13

  3 omega   -7.00   19.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000   90.0000 13

  4 omega   -1.00   31.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000    0.0000 16

  5 omega  -45.00   47.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  -30.0000 46

  6 omega    2.00   92.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  120.0000 45

  7 omega  -48.00   46.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -150.0000 47
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0805933000
_diffrn_orient_matrix_UB_12      -0.0088002000
_diffrn_orient_matrix_UB_13      0.0377088000
_diffrn_orient_matrix_UB_21      0.0929019000
_diffrn_orient_matrix_UB_22      -0.0025797000
_diffrn_orient_matrix_UB_23      0.0380085000
_diffrn_orient_matrix_UB_31      0.0008112000
_diffrn_orient_matrix_UB_32      0.0696014000
_diffrn_orient_matrix_UB_33      0.0088757000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4881
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.53
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0440P)^2^+0.3012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1212
_reflns_number_gt                2328
_reflns_number_total             3006
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02440_si_003.cif
_cod_data_source_block           2641
_cod_original_cell_volume        765.9(2)
_cod_database_code               4035692
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3A)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_date_sample_data_collection 2018-07-27
_olex2_submission_special_instructions 'No special instructions were received'