Photochemical Synthesis of 2-Azabicyclo[3.2.0]heptanes: Advanced Building Blocks for Drug Discovery. Synthesis of 2,3-Ethanoproline.
Druzhenko, Tetiana; Skalenko, Yevhen; Samoilenko, Maryna; Denisenko, Aleksandr; Zozulya, Sergey; Borysko, Petro O.; Sokolenko, Maria I.; Tarasov, Alexandr; Mykhailiuk, Pavel K.; The Journal of organic chemistry 83 (2018) 1394–1401; doi:10.1021/acs.joc.7b02910

data_4033361
_publ_section_title
;
 Photochemical Synthesis of 2-Azabicyclo[3.2.0]heptanes: Advanced Building
 Blocks for Drug Discovery. Synthesis of 2,3-Ethanoproline.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1394
_journal_page_last               1401
_journal_paper_doi               10.1021/acs.joc.7b02910
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C16 H17 F3 I N O3'
_chemical_formula_weight         455.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.832(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8527(3)
_cell_length_b                   13.2507(4)
_cell_length_c                   13.5893(5)
_cell_measurement_reflns_used    3332
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7
_cell_measurement_theta_min      3.7
_cell_volume                     1698.14(10)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17164
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         3.383
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.931
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.853
_refine_diff_density_min         -1.301
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       0.0190(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0761P)^2^+0.3973P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1559
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3609
_reflns_number_total             4921
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02910_si_004.cif
_cod_data_source_block           tolm318
_cod_depositor_comments
'Adding full bibliography for 4033361--4033363.cif.'
_cod_database_code               4033361
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.699
_shelx_estimated_absorpt_t_max   0.910
_shelx_hkl_checksum              66968