Stereoselective synthesis of backbone extended π-conjugated amino esters.
Nalawade, Sachin A.; Singh, Manjeet; Puneeth Kumar, DRGKoppalu R; Dey, Sanjit; Gopi, Hosahudya N.; Organic & biomolecular chemistry 21 (2023) 2586–2595; doi:10.1039/d3ob00090g

data_7159200
_publ_section_title
;
 Stereoselective synthesis of backbone extended &#x3c0;-conjugated amino
 esters.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2586
_journal_page_last               2595
_journal_paper_doi               10.1039/d3ob00090g
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration S
_chemical_formula_moiety         'C12 H23 N O3'
_chemical_formula_sum            'C12 H23 N O3'
_chemical_formula_weight         229.31
_chemical_name_common
'(tert-butyl (S,E)-(6-hydroxy-2-methylhex-4-en-3-yl)carbamate)'
_chemical_name_systematic
'(tert-butyl (S,E)-(6-hydroxy-2-methylhex-4-en-3-yl)carbamate)'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-10-17 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3864(10)
_cell_length_b                   10.5866(17)
_cell_length_c                   19.684(3)
_cell_measurement_reflns_used    2590
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.823
_cell_measurement_theta_min      4.492
_cell_volume                     1330.8(4)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  microfocus
_diffrn_measurement_method       APEXIII
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12047
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.823
_diffrn_reflns_theta_min         4.492
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS,2008
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_description       needle-shape
_exptl_crystal_F_000             504.0
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 759 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.65(14)
_refine_ls_extinction_coef       0.0064(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2590
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0215P)^2^+0.5503P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.658
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.911
_reflns_number_gt                2161
_reflns_number_total             2590
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00090g2.cif
_cod_data_source_block           3a
_cod_depositor_comments
'Adding full bibliography for 7159200--7159209.cif.'
_cod_database_code               7159200
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.968
_exptl_absorpt_special_details   multi-scan
_shelx_res_checksum              46600