Copper(ii) accelerated azide‒alkyne cycloaddition reaction using mercaptopyridine-based triazole ligands
Gonzalez-Silva, Karen; Rendon-Nava, David; Alvarez-Hernández, Alejandro; Mendoza-Espinosa, Daniel; New Journal of Chemistry 43 (2019) 16538–; doi:10.1039/C9NJ03974K

data_7058862
_publ_section_title
;
 Copper(ii) accelerated azide--alkyne cycloaddition reaction using
 mercaptopyridine-based triazole ligands
;
_journal_issue                   42
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16538
_journal_paper_doi               10.1039/C9NJ03974K
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C34 H38 Cl4 Cu2 N8 O S2, C2 H5 O'
_chemical_formula_sum            'C36 H43 Cl4 Cu2 N8 O2 S2'
_chemical_formula_weight         952.78
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-29 deposited with the CCDC.    2019-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                73.700(3)
_cell_angle_beta                 68.919(3)
_cell_angle_gamma                66.430(4)
_cell_formula_units_Z            2
_cell_length_a                   12.4862(4)
_cell_length_b                   13.9075(5)
_cell_length_c                   14.5276(5)
_cell_measurement_reflns_used    10103
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.3750
_cell_measurement_theta_min      3.2290
_cell_volume                     2129.73(14)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
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)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3659
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
  1 omega  -81.00   37.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824   19.0000 -120.0000 118

  2 omega  -21.00   28.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824   38.0000   90.0000 49

  3 omega  -26.00   32.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824   38.0000  -60.0000 58

  4 omega    1.00   81.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       42.4824  -99.0000   30.0000 80

  5 omega   19.00   76.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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  6 omega   14.00   64.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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  7 omega   40.00   66.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   37.00   73.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega  114.00  145.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -77.0000  -90.0000 31

 10 omega   43.00   86.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 11 omega   42.00   68.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000 -120.0000 26

 12 omega   64.00  123.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -130.0000  108.0000 59

 13 omega  105.00  174.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 14 omega   31.00   93.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000 -150.0000 62

 15 omega   54.00   86.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 16 omega   84.00  156.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 17 omega   78.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -125.0000  -60.0000 43

 18 omega   39.00   86.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000    0.0000 47

 19 omega   32.00   86.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000  150.0000 54

 20 omega   98.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000   60.0000 79

 21 omega   76.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -125.0000   30.0000 45

 22 omega   59.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000   90.0000 50

 23 omega   69.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -125.0000 -150.0000 52

 24 omega   43.00   84.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000  -60.0000 41

 25 omega   95.00  126.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  -30.0000 31

 26 omega  137.00  168.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  -30.0000 31

 27 omega   66.00   95.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000  150.0000 29

 28 omega  109.00  135.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  125.0000 -120.0000 26

 29 omega  104.00  130.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  125.0000  -30.0000 26

 30 omega   52.00   78.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000 -180.0000 26

 31 omega   39.00  100.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -77.0000  -90.0000 61

 32 omega -119.00  -10.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824  -77.0000   90.0000 109

 33 omega  -50.00   32.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824   38.0000    0.0000 82

 34 omega -117.00  -18.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824  -38.0000  -90.0000 99

 35 omega -115.00  -14.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824  -57.0000 -150.0000 101

 36 omega   18.00   99.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       42.4824 -125.0000 -180.0000 81

 37 omega   10.00  119.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       42.4824   77.0000   30.0000 109

 38 omega   61.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   15.0000  -90.0000 117

 39 omega   85.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   61.0000 -180.0000 93

 40 omega   81.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   77.0000  -30.0000 97

 41 omega   81.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   77.0000   90.0000 97

 42 omega   86.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   30.0000   60.0000 92

 43 omega   88.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  -60.0000 90

 44 omega   81.00  169.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   77.0000 -120.0000 88

 45 omega   85.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   61.0000  150.0000 93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0361387000
_diffrn_orient_matrix_UB_12      0.0723359000
_diffrn_orient_matrix_UB_13      -0.0935493000
_diffrn_orient_matrix_UB_21      -0.1138251000
_diffrn_orient_matrix_UB_22      0.0714711000
_diffrn_orient_matrix_UB_23      0.0669908000
_diffrn_orient_matrix_UB_31      0.0735864000
_diffrn_orient_matrix_UB_32      0.0681823000
_diffrn_orient_matrix_UB_33      -0.0040551000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            36855
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
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_diffrn_reflns_theta_min         3.303
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51906
_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_density_diffrn    1.486
_exptl_crystal_F_000             978
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     496
_refine_ls_number_reflns         8976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0694P)^2^+5.7196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1732
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7081
_reflns_number_total             8976
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj03974k2.cif
_cod_data_source_block           dme-45
_cod_depositor_comments          'Adding full bibliography for 7058862.cif.'
_cod_original_cell_volume        2129.73(15)
_cod_database_code               7058862
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C12 H26 N6 Cu Cl2'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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, All O(H) groups, All O(H,H) groups
2.a Rotating group:
 O1(H1A,H1B)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C0AA(H0AA,H0AB)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C25(H25), C22(H22), C30(H30), C21(H21), C20(H20), C19(H19), C7(H7),
 C17(H17), C5(H5), C28(H28), C16(H16), C14(H14), C15(H15), C36(H36)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C), C33(H33A,H33B,H33C), C11(H11A,H11B,
 H11C), C35(H35A,H35B,H35C), C34(H34A,H34B,H34C), C37(H37A,H37B,H37C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'