Copper(I)-Catalyzed Three-Component Click/Alkynylation: One-Pot Synthesis of 5-Alkynyl-1,2,3-triazoles.
Wang, Weiguo; Wei, Fang; Ma, Yudao; Tung, Chen-Ho; Xu, Zhenghu; Organic letters 18 (2016) 4158–4161; doi:10.1021/acs.orglett.6b02199

data_1555721
_publ_section_title
;
 Copper(I)-Catalyzed Three-Component Click/Alkynylation: One-Pot Synthesis
 of 5-Alkynyl-1,2,3-triazoles.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4158
_journal_page_last               4161
_journal_paper_doi               10.1021/acs.orglett.6b02199
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C24 H19 N3 O'
_chemical_formula_sum            'C24 H19 N3 O'
_chemical_formula_weight         365.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-07-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                104.203(6)
_cell_angle_beta                 90.641(6)
_cell_angle_gamma                96.358(5)
_cell_formula_units_Z            4
_cell_length_a                   9.973(6)
_cell_length_b                   10.372(6)
_cell_length_c                   19.048(11)
_cell_measurement_reflns_used    5513
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.445
_cell_measurement_theta_min      2.549
_cell_volume                     1896.8(19)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17112
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.55
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1194 before and 0.0532 after correction.
The Ratio of minimum to maximum transmission is 0.7316.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         6491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0570
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1716
_reflns_number_gt                4141
_reflns_number_total             6491
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02199_si_002.cif
_cod_data_source_block           p
_cod_depositor_comments
;

2022-03-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C24 H19 N3 O)'
_cod_original_formula_sum        'C48 H38 N6 O2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     730.84
_cod_database_code               1555721
_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:
 C18(H18A,H18B), C42(H42A,H42B)
2.b Aromatic/amide H refined with riding coordinates:
 C41(H41), C5(H5), C37(H37), C12(H12), C3(H3), C27(H27), C13(H13), C6(H6),
 C2(H2), C16(H16), C28(H28), C20(H20), C15(H15), C30(H30), C40(H40), C1(H1),
 C31(H31), C39(H39), C38(H38), C24(H24), C48(H48), C44(H44), C45(H45), C22(H22),
  C23(H23), C21(H21), C46(H46), C47(H47)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'