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_4032583
_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         'C24 H28 O7'
_chemical_formula_sum            'C24 H28 O7'
_chemical_formula_weight         428.46
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-05
_audit_creation_method
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Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.534(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9808(6)
_cell_length_b                   19.6620(8)
_cell_length_c                   11.5438(7)
_cell_measurement_reflns_used    1908
_cell_measurement_temperature    293.6(4)
_cell_measurement_theta_max      23.7470
_cell_measurement_theta_min      4.0470
_cell_volume                     2265.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.6(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details
;
  1 omega  -32.00   -4.70   1.0500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.9586   77.0000  -60.0000 26

  2 omega  -39.00   87.00   1.0500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       23.0992   19.0000  150.0000 120

  3 omega    4.00   30.25   1.0500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -19.0000  120.0000 25

  4 omega  -94.00  -48.85   1.0500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -19.0000  120.0000 43

  5 omega   41.00   83.00   1.0500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000   60.0000 40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0576772000
_diffrn_orient_matrix_UB_12      0.0012576000
_diffrn_orient_matrix_UB_13      0.0362856000
_diffrn_orient_matrix_UB_21      0.0300404000
_diffrn_orient_matrix_UB_22      -0.0260781000
_diffrn_orient_matrix_UB_23      -0.0333215000
_diffrn_orient_matrix_UB_31      0.0285747000
_diffrn_orient_matrix_UB_32      0.0249070000
_diffrn_orient_matrix_UB_33      -0.0367550000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9778
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.39
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0580
_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^)+(0.0541P)^2^+0.6683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1610
_reflns_number_gt                2562
_reflns_number_total             4279
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00879_si_004.cif
_cod_data_source_block           zhenlan_0905
_cod_depositor_comments
'Adding full bibliography for 4032583--4032584.cif.'
_cod_database_code               4032583
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 95.26
_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:
 C4(H4A,H4B), C7(H7A,H7B), C9(H9A,H9B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C)
;
_olex2_date_sample_data_collection 2016-09-05
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.610
_oxdiff_exptl_absorpt_empirical_full_min 0.764