Exploiting a Difference in Leaving Group Ability: An Approach to β-Substituted Monofluoroalkenes Using gem-Chlorofluoropropenes.
Hamel, Jean-Denys; Cloutier, Mélissa; Paquin, Jean-François; Organic letters 18 (2016) 1852–1855; doi:10.1021/acs.orglett.6b00590

data_1555523
_publ_section_title
;
 Exploiting a Difference in Leaving Group Ability: An Approach to
 \b-Substituted Monofluoroalkenes Using gem-Chlorofluoropropenes.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1852
_journal_page_last               1855
_journal_paper_doi               10.1021/acs.orglett.6b00590
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C17 H25 F N O, Cl'
_chemical_formula_sum            'C17 H25 Cl F N O'
_chemical_formula_weight         313.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2014-10-08
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.8818(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3762(8)
_cell_length_b                   9.6596(6)
_cell_length_c                   13.4588(8)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.60
_cell_volume                     1735.01(18)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18661
_diffrn_reflns_theta_full        28.2288
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         1.53
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0936 before and 0.0367 after correction.
The Ratio of minimum to maximum transmission is 0.9364.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.2014
_exptl_crystal_description       plate
_exptl_crystal_F_000             672.8915
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.3664
_refine_diff_density_min         -0.1989
_refine_diff_density_rms         0.0450
_refine_ls_d_res_high            0.7513
_refine_ls_d_res_low             13.3455
_refine_ls_goodness_of_fit_ref   1.0425
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    37
_refine_ls_number_parameters     196
_refine_ls_number_reflns         4270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0425
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0423P)^2^+0.5329P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0887
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              17
_reflns_limit_h_min              -17
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3689
_reflns_number_total             4270
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ol6b00590_si_002.cif
_cod_data_source_block           JDR1007_0m
_cod_database_code               1555523
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C2(H2a,H2b), C3(H3a,H3b), C4(H4a,H4b), C5(H5a,H5b)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c), C17(H17a,H17b,H17c)
;
_olex2_submission_special_instructions 'No special instructions were received'