Noncovalent Interactions of Fluorine with Amide and CH<sub>2</sub> Groups in N-Phenyl γ-Lactams: Covalently Identical Fluorine Atoms in Nonequivalent Chemical Environments.
Xi, Ning; Sun, Xiaohua; Li, Minxiong; Sun, Mingming; Xi, Michael A.; Zhan, Zeping; Yao, Jia; Bai, Xu; Wu, Yanjun; Liao, Min; The Journal of organic chemistry 83 (2018) 11586–11594; doi:10.1021/acs.joc.8b01562

data_4035285
_publ_section_title
;
 Noncovalent Interactions of Fluorine with Amide and CH<sub>2</sub> Groups
 in N-Phenyl \g-Lactams: Covalently Identical Fluorine Atoms in
 Nonequivalent Chemical Environments.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11586
_journal_page_last               11594
_journal_paper_doi               10.1021/acs.joc.8b01562
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H11 F2 N O'
_chemical_formula_weight         211.21
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   8.7532(3)
_cell_length_b                   9.7766(3)
_cell_length_c                   11.3827(3)
_cell_measurement_reflns_used    3175
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      65.0610
_cell_measurement_theta_min      5.9460
_cell_volume                     974.09(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.5058
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5040
_diffrn_reflns_theta_full        65.27
_diffrn_reflns_theta_max         65.27
_diffrn_reflns_theta_min         5.97
_exptl_absorpt_coefficient_mu    1.014
_exptl_absorpt_correction_T_max  0.9233
_exptl_absorpt_correction_T_min  0.7507
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.18(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+0.0660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0827
_reflns_number_gt                1501
_reflns_number_total             1610
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01562_si_001.cif
_cod_data_source_block           Compound_2
_cod_database_code               4035285