Iron-Catalyzed Radical [2 + 2 + 2] Annulation of Benzene-Linked 1,7-Enynes with Aldehydes: Fused Pyran Compounds.
Lv, Leiyang; Li, Zhiping; Organic letters 18 (2016) 2264–2267; doi:10.1021/acs.orglett.6b00902

data_1555555
_publ_section_title
;
 Iron-Catalyzed Radical [2 + 2 + 2] Annulation of Benzene-Linked
 1,7-Enynes with Aldehydes: Fused Pyran Compounds.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2264
_journal_page_last               2267
_journal_paper_doi               10.1021/acs.orglett.6b00902
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C33 H26 Cl N O5 S'
_chemical_formula_sum            'C33 H26 Cl N O5 S'
_chemical_formula_weight         584.06
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-15
_audit_creation_method
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Olex2 1.2
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_cell_length_c                   12.5597(16)
_cell_measurement_reflns_used    1743
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      26.3740
_cell_measurement_theta_min      3.4260
_cell_volume                     2892.9(6)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega  -65.00   22.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -38.0000  150.0000 87

  2 omega  -30.00   52.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -19.0000 -150.0000 82
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0385793000
_diffrn_orient_matrix_UB_12      0.0023634000
_diffrn_orient_matrix_UB_13      0.0381494000
_diffrn_orient_matrix_UB_21      0.0321455000
_diffrn_orient_matrix_UB_22      0.0262729000
_diffrn_orient_matrix_UB_23      0.0187061000
_diffrn_orient_matrix_UB_31      -0.0530071000
_diffrn_orient_matrix_UB_32      0.0141209000
_diffrn_orient_matrix_UB_33      -0.0413597000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0999
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11234
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.324
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         5656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1260
_refine_ls_R_factor_gt           0.0721
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0990P)^2^+0.0100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1680
_refine_ls_wR_factor_ref         0.2180
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3276
_reflns_number_total             5656
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00902_si_002.cif
_cod_data_source_block           exp_6142
_cod_database_code               1555555
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C33 H26 O2 Cl1 N1 S1'
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.976
_reflns_odcompleteness_completeness 98.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C28(H28), C29(H29),
  C31(H31), C32(H32)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              40185
_shelx_hkl_checksum              89853
_olex2_submission_special_instructions 'No special instructions were received'