Iron-catalyzed decarbonylation initiated [2 + 2 + m] annulation of benzene-linked 1,n-enynes with aliphatic aldehydes
Lv, Leiyang; Bai, Xiaohui; Yan, Xiaoyu; Li, Zhiping; Organic Chemistry Frontiers 3 (2016) 1509–; doi:10.1039/C6QO00429F

data_1553516
_publ_section_title
;
 Iron-catalyzed decarbonylation initiated [2 + 2 + m] annulation of
 benzene-linked 1,n-enynes with aliphatic aldehydes
;
_journal_issue                   11
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1509
_journal_paper_doi               10.1039/C6QO00429F
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C33 H35 N O4 S'
_chemical_formula_sum            'C33 H35 N O4 S'
_chemical_formula_weight         541.68
_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             2016-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-07-16 deposited with the CCDC.
2016-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.550(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4186(13)
_cell_length_b                   11.3388(8)
_cell_length_c                   16.9081(14)
_cell_measurement_reflns_used    2590
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      27.1860
_cell_measurement_theta_min      3.0710
_cell_volume                     2818.4(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -19.00   73.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017   57.0000    0.0000 92

  2 omega  -65.00   33.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -77.0000 -120.0000 98

  3 omega  -20.00   11.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -99.0000 -180.0000 31
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0202000000
_diffrn_orient_matrix_UB_12      0.0082429000
_diffrn_orient_matrix_UB_13      0.0432495000
_diffrn_orient_matrix_UB_21      0.0124785000
_diffrn_orient_matrix_UB_22      0.0582020000
_diffrn_orient_matrix_UB_23      -0.0073744000
_diffrn_orient_matrix_UB_31      -0.0420127000
_diffrn_orient_matrix_UB_32      0.0213318000
_diffrn_orient_matrix_UB_33      0.0033696000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0800
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14537
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.070
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79567
_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_density_diffrn    1.277
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0457P)^2^+1.0085P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1358
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3461
_reflns_number_total             5526
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00429f2.cif
_cod_data_source_block           exp_7090
_cod_database_code               1553516
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C33 O4 N1 S1'
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.977
_reflns_odcompleteness_completeness 99.73
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23), C28(H28), C29(H29), C31(H31), C32(H32)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C33(H33A,H33B,H33C)
;
_olex2_submission_special_instructions 'No special instructions were received'