An insight into the synthesis of novel aryl-substituted alicyclic β-amino acid derivatives through substrate-directed palladium-catalysed regio- and stereoselective cross-coupling
Nonn, Melinda; Kiss, Lorand; Hänninen, Mikko; Fulop, Ferenc; RSC Adv.  (2015) –; doi:10.1039/C4RA16196C

data_7219285
_publ_section_title
;
 An insight into the synthesis of novel aryl-substituted alicyclic
 \b-amino acid derivatives through substrate-directed palladium-catalysed
 regio- and stereoselective cross-coupling
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA16196C
_journal_year                    2015
_chemical_formula_moiety         'C19 H25 N O4'
_chemical_formula_sum            'C19 H25 N O4'
_chemical_formula_weight         331.40
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2014-12-10 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.778(3)
_cell_length_b                   6.9181(14)
_cell_length_c                   17.853(4)
_cell_measurement_reflns_used    2457
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      0.41
_cell_measurement_wavelength     0.71073
_cell_volume                     1825.2(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            '95mm CCD camera on \k-goniostat'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_UB_11      0.049678
_diffrn_orient_matrix_UB_12      -0.059198
_diffrn_orient_matrix_UB_13      0.019029
_diffrn_orient_matrix_UB_21      -0.075075
_diffrn_orient_matrix_UB_22      -0.032407
_diffrn_orient_matrix_UB_23      -0.039584
_diffrn_orient_matrix_UB_31      0.112816
_diffrn_orient_matrix_UB_32      0.004502
_diffrn_orient_matrix_UB_33      -0.034721
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3465
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.666
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1951
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      14.476
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0549
_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^)+(0.0646P)^2^+0.8478P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1478
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1585
_reflns_number_total             1951
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra16196c2.cif
_cod_data_source_block           KLHN53
_cod_original_cell_volume        1825.2(6)
_cod_database_code               7219285
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H4 of C4, H19A of C19A, H20A of C20A, H21 of C21, H20B
  of C20B, {H19B,H8A,H8B} of C19B
 At 1.5 times of:
  {H16A,H16B,H16C} of C16, {H15A,H15B,H15C} of C15, {H9A,H9B,H9C} of C9, H11
  of C19B
2. Restrained distances
 N11-H11
 0.87 with sigma of 0.005
 C9-C8
 1.54 with sigma of 0.01
 H8B-C8 = H8B-H8A
 0.99 with sigma of 0.001
 C18-C19A = C19A-C20A = C20A-C21 = C21-C20B_$1 = C20B_$1-C19B_$1 = C19B_$1-C18
 = C18-C19B = C19B-C20B
 1.39 with sigma of 0.005
 H8A-H8B
 1.615 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
C18 \\sim C19A \\sim C20A \\sim C21 \\sim C20B \\sim C19B: within 2A with sigma
of 0.005 and sigma for terminal atoms of 0.01
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C20B) \\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4. Others
 Fixed Sof: H5B(0.5) H5A(0.5) H3A(0.5) H3B(0.5) H16A(0.5) H16B(0.5) H16C(0.5)
 C8(0.5) C19A(0.5) H19A(0.5) C4(0.5) H4(0.5) C20A(0.5) H20A(0.5) C9(0.5)
 H9A(0.5) H9B(0.5) H9C(0.5) C21(0.5) H21(0.5) C20B(0.5) H20B(0.5) C19B(0.5)
 H19B(0.5) H8B(0.5)
5.a Ternary CH refined with riding coordinates:
 C4(H4)
5.b Secondary CH2 refined with riding coordinates:
 C5(H5B,H5A), C3(H3A,H3B)
5.c Aromatic/amide H refined with riding coordinates:
 C19A(H19A), C20A(H20A), C21(H21), C20B(H20B), C19B(H19B)
5.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C9(H9A,H9B,H9C)
;