Toward a Stable α-Cycloalkyl Amino Acid with a Photoswitchable Cationic Side Chain
Riccardo Rossi Paccani; Donato Donati; Stefania Fusi; Loredana Latterini; Grazia Farina; Vinicio Zanirato; Massimo Olivucci; Journal of Organic Chemistry 77 (2012) 1738–1748; doi:10.1021/jo2022263

data_4026956
_publ_contact_author_address
'Department of Chemistry, University of Siena, Via A. Moro, 2 53100 Siena-Italy'
_publ_contact_author_email       rossipaccani@unisi.it
_publ_contact_author_name        'Rossi Paccani Riccardo'
_publ_section_title
;
 Toward a Stable \a-Cycloalkyl Amino Acid with a Photoswitchable Cationic
 Side Chain
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1738
_journal_page_last               1748
_journal_paper_doi               10.1021/jo2022263
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C15 H14 F3 N O5'
_chemical_formula_weight         345.27
_chemical_name_systematic
;
 ethyl 5-methoxy-1-oxo-2-(2,2,2-trifluoroacetamido)-2,3-dihydro
-1H-indene-2-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.90(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.214(8)
_cell_length_b                   9.281(5)
_cell_length_c                   9.715(5)
_cell_measurement_reflns_used    53
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.84
_cell_measurement_theta_min      5.25
_cell_volume                     1587.0(14)
_computing_cell_refinement       'XSCANS (Siemens, 1994)'
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        'XSCANS (Siemens, 1994)'
_computing_molecular_graphics    'Ortep-3 (Farrugia, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3596
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.16
_diffrn_standards_decay_%        0.0(2)
_diffrn_standards_interval_count 197
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'XEMP, Siemens, 1989'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0.206
_refine_ls_shift/su_mean         0.020
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0846P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1537
_reflns_number_gt                1728
_reflns_number_total             2738
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2022263_si_003.cif
_cod_data_source_block           rrp57
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026956