Copper-Catalyzed One-Pot Synthesis of 1,3-Enynes from 2-Chloro-<i>N</i>-(quinolin-8-yl)acetamides and Terminal Alkynes.
Zhu, Lifan; Guo, Hongyu; Feng, Xiujuan; Yamamoto, Yoshinori; Bao, Ming; The Journal of organic chemistry 85 (2020) 8740–8748; doi:10.1021/acs.joc.0c01102

data_4038498
_publ_section_title
;
 Copper-Catalyzed One-Pot Synthesis of 1,3-Enynes from
 2-Chloro-<i>N</i>-(quinolin-8-yl)acetamides and Terminal Alkynes.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8740
_journal_page_last               8748
_journal_paper_doi               10.1021/acs.joc.0c01102
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C29 H18 F6 N2 O'
_chemical_formula_sum            'C29 H18 F6 N2 O'
_chemical_formula_weight         524.45
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.769(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.5939(6)
_cell_length_b                   13.7390(6)
_cell_length_c                   10.8510(4)
_cell_measurement_reflns_used    2233
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.52
_cell_measurement_theta_min      2.41
_cell_volume                     2437.98(17)
_computing_cell_refinement       'SAINT V8.32B (?, 2016)'
_computing_data_reduction        'SAINT V8.32B (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12577
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         1.936
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0676 before and 0.0391 after correction.
The Ratio of minimum to maximum transmission is 0.8817.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.0667
_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^)+(0.0985P)^2^+0.5709P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1783
_refine_ls_wR_factor_ref         0.2170
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2820
_reflns_number_total             5361
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01102_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 4038498.cif.'
_cod_database_code               4038498
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 N001(H001), C00I(H00I), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C012(H012)
;
_shelx_res_checksum              27796
_shelx_hkl_checksum              1088
_olex2_submission_special_instructions 'No special instructions were received'