Cu(I)-Catalyzed Tandem Reaction of Carbene Coupling and Horner-Wadsworth-Emmons Type Olefination: Access toward Enynes.
Zhou, Yujing; Ye, Fei; Zhou, Qi; Zhang, Yan; Wang, Jianbo; Organic letters 18 (2016) 2024–2027; doi:10.1021/acs.orglett.6b00631

data_1555524
_publ_section_title
;
 Cu(I)-Catalyzed Tandem Reaction of Carbene Coupling and
 Horner-Wadsworth-Emmons Type Olefination: Access toward Enynes.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2024
_journal_page_last               2027
_journal_paper_doi               10.1021/acs.orglett.6b00631
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-10-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.824(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4855(7)
_cell_length_b                   7.5481(6)
_cell_length_c                   13.9074(11)
_cell_measurement_reflns_used    1381
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      27.8200
_cell_measurement_theta_min      3.6220
_cell_volume                     677.30(11)
_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
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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)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   13.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  -99.0000  -30.0000 40

  2 omega  -65.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454    0.0000 -120.0000 146

  3 omega  -65.00  -30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  -38.0000   60.0000 35
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0367464000
_diffrn_orient_matrix_UB_12      0.0124584000
_diffrn_orient_matrix_UB_13      0.0493248000
_diffrn_orient_matrix_UB_21      -0.0930585000
_diffrn_orient_matrix_UB_22      0.0448957000
_diffrn_orient_matrix_UB_23      0.0076376000
_diffrn_orient_matrix_UB_31      -0.0455003000
_diffrn_orient_matrix_UB_32      -0.0815917000
_diffrn_orient_matrix_UB_33      0.0117629000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3583
_diffrn_reflns_point_group_measured_fraction_full 0.888
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         2.945
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85368
_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    1.247
_exptl_crystal_description
;
;
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 617 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -9.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2334
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0408P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1096
_reflns_Friedel_coverage         0.623
_reflns_Friedel_fraction_full    0.759
_reflns_Friedel_fraction_max     0.729
_reflns_number_gt                1871
_reflns_number_total             2334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00631_si_001.cif
_cod_data_source_block           exp_5834
_cod_original_cell_volume        677.29(10)
_cod_database_code               1555524
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C1 H1'
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.993
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
2.b :
 C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'