Unraveling the Role of Alkyl F on CH-π Interactions and Uncovering the Tipping Point for Fluorophobicity.
Ams, Mark R.; Fields, Michael; Grabnic, Timothy; Janesko, Benjamin G.; Zeller, Matthias; Sheridan, Rose; Shay, Amanda; The Journal of organic chemistry 80 (2015) 7764–7769; doi:10.1021/acs.joc.5b01072

data_4031326
_publ_section_title
;
 Unraveling the Role of Alkyl F on CH-\p Interactions and Uncovering the
 Tipping Point for Fluorophobicity.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7764
_journal_page_last               7769
_journal_paper_doi               10.1021/acs.joc.5b01072
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C27 H26 F2 N2 O2'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 75.381(6)
_cell_angle_gamma                74.812(6)
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_cell_length_b                   9.0503(12)
_cell_length_c                   15.703(2)
_cell_measurement_reflns_used    9838
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.5958
_cell_measurement_theta_min      2.9099
_cell_volume                     1084.8(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2014)'
_computing_data_collection       'Apex2 v2014.1-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_refinement
;  
SHELXL-2013 (Sheldrick, 2013), 
SHELXLE Rev645 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
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_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker AXS Prospector CCD diffractometer'
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_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
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_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.982
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_diffrn_reflns_limit_l_min       -18
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_diffrn_reflns_point_group_measured_fraction_full 0.965
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_diffrn_reflns_theta_max         67.238
_diffrn_reflns_theta_min         2.908
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2 v2014.1-0 (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       rod
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 3245 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     600
_refine_ls_number_reflns         7230
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0648
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1085P)^2^+1.1233P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1744
_refine_ls_wR_factor_ref         0.1764
_reflns_Friedel_coverage         0.978
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                7055
_reflns_number_total             7230
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           Prosp14mz018_0m
_cod_depositor_comments
'Adding full bibliography for 4031325--4031329.cif.'
_cod_database_code               4031326
_shelx_estimated_absorpt_t_min   0.805
_shelx_estimated_absorpt_t_max   0.961
_shelxl_version_number           2013-4
_shelx_res_checksum              38257
_shelx_hkl_checksum              89088