Metal-free cascade radical cyclization of 1,6-enynes with aldehydes
Jian-Yi Luo; Hui-Liang Hua; Zi-Sheng Chen; Zhao-Zhao Zhou; Yan-Fang Yang; Ping-Xin Zhou; Yu-Tao He; Xue-Yuan Liu; Yong-Min Liang; Chem.Commun. 50 (2014) 1564–; doi:10.1039/c3cc48339h

data_7111861
_publ_section_title
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 Metal-free cascade radical cyclization of 1,6-enynes with aldehydes
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_journal_name_full               Chem.Commun.
_journal_page_first              1564
_journal_paper_doi               10.1039/c3cc48339h
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C11 H10 F3 N O'
_chemical_formula_sum            'C11 H10 F3 N O'
_chemical_formula_weight         229.20
_chemical_name_systematic
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?
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_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-08
_audit_creation_method
;
Olex2 1.2
(compiled Dec 5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.331(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.6562(9)
_cell_length_b                   19.9373(18)
_cell_length_c                   12.6769(15)
_cell_measurement_temperature    293(2)
_cell_volume                     2137.3(4)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8622
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.16
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.127
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4070
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.2245
_refine_ls_R_factor_gt           0.1012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1569P)^2^+0.3752P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2881
_refine_ls_wR_factor_ref         0.3854
_reflns_number_gt                1376
_reflns_number_total             4070
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc48339h.txt
_cod_data_source_block           heyt0914
_cod_database_code               7111861
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
H16 of C16, {H19A,H19B} of C19, H14 of C14, H1 of C1, H5 of C5, {H8A,H8B}
of C8, H12 of C12, {H21C,H21D} of C21A, {H21A,H21B} of C21, H9 of C9, {H10A,
H10B} of C10, H20A of C20A, H9A of C9A, {H10C,H10D} of C10A, H13 of C13, H15
of C15, H2 of C2, H4 of C4, H3 of C3, H20 of C20
2. Others
Fixed Sof: C20(0.5) H20(0.5) C9(0.4) H9(0.4) C21(0.5) H21A(0.5) H21B(0.5)
C10(0.6) H10A(0.6) H10B(0.6) C21A(0.5) H21C(0.5) H21D(0.5) C20A(0.5) H20A(0.5)
C9A(0.6) H9A(0.6) C10A(0.4) H10C(0.4) H10D(0.4)
3.a Ternary CH refined with riding coordinates:
C20(H20), C9(H9), C20A(H20A), C9A(H9A)
3.b Secondary CH2 refined with riding coordinates:
C19(H19A,H19B), C8(H8A,H8B), C21(H21A,H21B), C10(H10A,H10B), C21A(H21C,H21D),
C10A(H10C,H10D)
3.c Aromatic/amide H refined with riding coordinates:
C12(H12), C16(H16), C14(H14), C1(H1), C5(H5), C13(H13), C15(H15), C2(H2),
C4(H4), C3(H3)
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