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_7111860
_publ_section_title
;
 Metal-free cascade radical cyclization of 1,6-enynes with aldehydes
;
_journal_name_full               Chem.Commun.
_journal_page_first              1564
_journal_paper_doi               10.1039/c3cc48339h
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C26 H24 Cl2 O5'
_chemical_formula_sum            'C26 H24 Cl2 O5'
_chemical_formula_weight         487.35
_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_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-09-23
_audit_creation_method
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Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
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_cell_angle_alpha                90
_cell_angle_beta                 91.490(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9958(3)
_cell_length_b                   15.4197(5)
_cell_length_c                   19.3202(6)
_cell_measurement_reflns_used    4263
_cell_measurement_temperature    294.11(10)
_cell_measurement_theta_max      70.5120
_cell_measurement_theta_min      4.5720
_cell_volume                     2381.24(14)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_molecular_graphics
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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
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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
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SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
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_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      294.11(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9372
_diffrn_measured_fraction_theta_max 0.9937
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1656858000
_diffrn_orient_matrix_UB_12      -0.0103037000
_diffrn_orient_matrix_UB_13      -0.0381571000
_diffrn_orient_matrix_UB_21      -0.0030196000
_diffrn_orient_matrix_UB_22      0.0972737000
_diffrn_orient_matrix_UB_23      -0.0181728000
_diffrn_orient_matrix_UB_31      0.0983765000
_diffrn_orient_matrix_UB_32      0.0203914000
_diffrn_orient_matrix_UB_33      0.0676456000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12176
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         70.702
_diffrn_reflns_theta_min         3.668
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.3100
_exptl_crystal_size_mid          0.2500
_exptl_crystal_size_min          0.2400
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4548
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0947P)^2^+0.7346P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1541
_refine_ls_wR_factor_ref         0.1670
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3747
_reflns_number_total             4548
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3cc48339h.txt
_cod_data_source_block           luojy0923
_cod_original_cell_volume        2381.25(14)
_cod_database_code               7111860
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 93.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C23(H23), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C19(H19A,H19B,
 H19C)
;
_shelx_res_checksum              2837
_shelx_hkl_checksum              93418