Sustainable Difluoroalkylation Cyclization Cascades of 1,8-Enynes.
Huang, Honggui; Li, Yi; The Journal of organic chemistry 82 (2017) 4449–4457; doi:10.1021/acs.joc.7b00350

data_4032465
_publ_section_title
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 Sustainable Difluoroalkylation Cyclization Cascades of 1,8-Enynes.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4449
_journal_page_last               4457
_journal_paper_doi               10.1021/acs.joc.7b00350
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C29 H23 Br F2 N O3'
_chemical_formula_sum            'C29 H23 Br F2 N O3'
_chemical_formula_weight         551.39
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                77.526(3)
_cell_angle_beta                 70.388(4)
_cell_angle_gamma                79.507(4)
_cell_formula_units_Z            2
_cell_length_a                   9.654(3)
_cell_length_b                   10.951(3)
_cell_length_c                   13.265(4)
_cell_measurement_reflns_used    2439
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.992
_cell_measurement_theta_min      2.897
_cell_volume                     1280.7(7)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.755
_diffrn_measured_fraction_theta_max 0.775
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.755
_diffrn_reflns_Laue_measured_fraction_max 0.775
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4257
_diffrn_reflns_point_group_measured_fraction_full 0.755
_diffrn_reflns_point_group_measured_fraction_max 0.775
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         1.918
_exptl_absorpt_coefficient_mu    1.650
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       plate
_exptl_crystal_F_000             562
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3495
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0634
_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^)+(0.0967P)^2^+2.4681P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.1890
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2439
_reflns_number_total             3495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00350_si_002.cif
_cod_data_source_block           p-1
_cod_database_code               4032465
_shelxl_version_number           2013-2
_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. Uiso/Uaniso restraints and constraints
C29 \\sim C28: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04
Uanis(C28) \\sim Ueq, Uanis(C29) \\sim Ueq, : with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C2(H2), C13(H13), C20(H20), C17(H17), C19(H19), C11(H11),
 C18(H18), C10(H10), C28(H28), C9(H9)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C24(H24A,H24B,H24C), C29(H29A,H29B,H29C)
;
_olex2_submission_special_instructions 'No special instructions were received'