Executing and Rationalizing the Synthesis of a Difluorinated Analogue of a Ring-Expanded Calystegine B2
Sara H. Kyne; Jonathan A. L. Miles; Jonathan M. Percy; Kuldip Singh; Journal of Organic Chemistry 77 (2012) 991–998; doi:10.1021/jo2022845

data_4026902
_publ_section_title
;
 Executing and Rationalizing the Synthesis of a Difluorinated Analogue of
 a Ring-Expanded Calystegine B2
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              991
_journal_page_last               998
_journal_paper_doi               10.1021/jo2022845
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C15 H19 F2 N O3'
_chemical_formula_sum            'C15 H19 F2 N O3'
_chemical_formula_weight         299.31
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.428(3)
_cell_length_b                   24.352(6)
_cell_length_c                   10.474(2)
_cell_measurement_reflns_used    870
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.25
_cell_measurement_theta_min      2.77
_cell_volume                     2914.9(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19696
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
absorption correction based on 8492 reflections (SADABS); Rint 0.052 
before correction and 0.036 after.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0561P)^2^+0.9465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1194
_reflns_number_gt                2233
_reflns_number_total             2576
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2022845_si_003_2.cif
_cod_data_source_block           13a
_cod_original_cell_volume        2915.0(12)
_cod_database_code               4026902