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_4026955
_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_moiety         'C19 H17 F3 N2 O3'
_chemical_formula_sum            'C19 H17 F3 N2 O3'
_chemical_formula_weight         378.35
_chemical_name_systematic
;
 2,2,2-trifluoro-N-(8-methoxy-3-methyl-5-oxo-1,2,3,5,5a,6_
-hexahydroindeno[1,2-e]indol-5a-yl)acetamide
;
_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           'CrysAlisPro, Oxf...'
_cell_angle_alpha                90.00
_cell_angle_beta                 101.658(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6439(4)
_cell_length_b                   19.2458(9)
_cell_length_c                   9.3848(6)
_cell_measurement_reflns_used    2397
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0435
_cell_measurement_theta_min      2.1530
_cell_volume                     1705.93(16)
_computing_cell_refinement       'CrysAlisPro, Oxf...'
_computing_data_collection       'CrysAlisPro, Oxf...'
_computing_data_reduction        'CrysAlisPro, Oxf...'
_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_detector_area_resol_mean 16.0827
_diffrn_measured_fraction_theta_full 0.857
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0809
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8174
_diffrn_reflns_theta_full        29.08
_diffrn_reflns_theta_max         29.08
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro, Oxford Diffraction Ltd.,
 Version 1.171.33.42
 empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.3548
_exptl_crystal_size_mid          0.2654
_exptl_crystal_size_min          0.0978
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.791
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.791
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0397P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0832
_reflns_number_gt                1825
_reflns_number_total             3922
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2022263_si_002.cif
_cod_data_source_block           ste3
_cod_original_cell_volume        1705.93(15)
_cod_database_code               4026955