Copper-Catalyzed [2 + 2 + 3] Annulation of 1,6-Enynes with α-Bromo-1,3-Dicarbonyl Compounds: Synthesis of Dihydrooxepines.
Zheng, Lan; Liang, Yong-Min; The Journal of organic chemistry 82 (2017) 7000–7007; doi:10.1021/acs.joc.7b00879

data_4032584
_publ_section_title
;
 Copper-Catalyzed [2 + 2 + 3] Annulation of 1,6-Enynes with
 \a-Bromo-1,3-Dicarbonyl Compounds: Synthesis of Dihydrooxepines.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7000
_journal_page_last               7007
_journal_paper_doi               10.1021/acs.joc.7b00879
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C26 H28 Br N O5 S'
_chemical_formula_sum            'C26 H28 Br N O5 S'
_chemical_formula_weight         546.46
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-05-27
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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_cell_angle_alpha                67.547(16)
_cell_angle_beta                 63.377(19)
_cell_angle_gamma                67.270(19)
_cell_formula_units_Z            2
_cell_length_a                   11.325(2)
_cell_length_b                   11.6605(19)
_cell_length_c                   11.833(2)
_cell_measurement_reflns_used    1845
_cell_measurement_temperature    289.69(10)
_cell_measurement_theta_max      23.1170
_cell_measurement_theta_min      3.9050
_cell_volume                     1246.5(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      289.69(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -38.00  -12.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479   57.0000   60.0000 17

  2 omega   -9.00   27.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000  -60.0000 24

  3 omega  -47.00   37.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000   60.0000 56

  4 omega   -2.00   25.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  -30.0000 18

  5 omega   -7.00   44.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000  150.0000 34

  6 omega  -46.00   41.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000  -60.0000 58

  7 omega  -20.00   56.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000 -180.0000 51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0708251000
_diffrn_orient_matrix_UB_12      -0.0196173000
_diffrn_orient_matrix_UB_13      -0.0358807000
_diffrn_orient_matrix_UB_21      0.0074196000
_diffrn_orient_matrix_UB_22      0.0603616000
_diffrn_orient_matrix_UB_23      -0.0072184000
_diffrn_orient_matrix_UB_31      0.0139565000
_diffrn_orient_matrix_UB_32      -0.0248823000
_diffrn_orient_matrix_UB_33      0.0588577000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8630
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4886
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+0.5314P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                3254
_reflns_number_total             4886
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00879_si_002.cif
_cod_data_source_block           zhenglan_0512
_cod_depositor_comments
'Adding full bibliography for 4032583--4032584.cif.'
_cod_original_cell_volume        1246.4(4)
_cod_database_code               4032584
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14), C20(H20), C21(H21), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C25(H25A,H25B,
 H25C)
;
_olex2_date_sample_data_collection 2016-05-13
_olex2_submission_special_instructions 'No special instructions were received'